Author(s): R. Benassi, C. Bertarini, L. Hilfert, G. Kempter, E. Kleinpeter, J. Spindler, F. Taddei and S. Thomas
Title: Exocyclic push-pull conjugated compounds. Part 3. An experimental NMR and theoretical MO ab initio study of the structure, the electronic properties and barriers to rotation about the exocyclic partial double bond in 2-exo-methylene- and 2-cyanoimino-quinazolines and -benzodiazepines
J. Mol. Struct. (Theochem.) Vol. 520, No. 1-3, p. 273-294 (2000); ISSN: 0166-1280; CODEN: THEODJ

keywords: push-pull ethylene; push-pull conjugated compounds; NMR spectroscopy; Ab initio study
Abstract:
The structure of a number of 2-exo-methylene substituted quinazolines and benzodiazepines, respectively, 1, 3a,b, I (X = -CN, -COOEt) and their 2-cyanoimino substituted analogues 2, 3c,d (X = -CN, -SO₂C₆H₄-Me(p) was completely assigned by the whole arsenal of 1D and 2D NMR spectroscopic methods, The E/Z isomerism at the exo-cyclic double bond was determined by both NMR spectroscopy and confirmed by ab initio quantum chemical calculations; the Z isomer is the preferred one, its amount proved dependent on steric hindrance. Due to the push-pull effect in this part of the molecules the restricted rotation about the partial C-2,C-11 and C-2,N-11 double bonds, could also be studied and the barrier to rotation measured by dynamic NMR spectroscopy. The free energies of activation of this dynamic process proved very similar along the compounds studied but being dependent on the polarity of the solvent. Quantum chemical calculations at the ab initio level were employed to prove the stereochemistry at the exo-cyclic partial double bonds of 1-4, to calculate the barriers to rotation but also to discuss in detail both the ground and the transition state of the latter dynamic process in order to better understand electronic, inter- and intramolecular effects on the barrier to rotation which could be determined experimentally in the cyanoimino substituted compounds 2, 3c,d, the MO ab initio calculations evidence the isomer interconversion to be better described by the internal rotation process than by the lateral shift mechanism.

Author(s): R. Benassi, C. Bertarini, E. Kleinpeter, F. Taddei and S. Thomas
Title: Exocyclic push-pull conjugated compounds. Part 1. Theoretical study of the effect of ring size on the structure, electronic properties and rotational barriers of cyclic analogoues of 1,1-diamino-2,2-dicyanoethylene
J. Mol. Struct. (Theochem.) Vol. 498, No. 1-3, p. 201-215 (2000); ISSN: 0166-1280; CODEN: THEODJ

keywords: push-pull ethylenes; electronic properties; rotational barrier; heterocyclic derivatives; conformations
Abstract:
An MO theoretical ab initio study was performed on 2-exo-methylene push-pull derivatives having as donor groups nitrogen atoms, components of a heterocyclic ring, and as acceptors CN and COOEt groups. Five-, six- and seven-membered ring derivatives were considered. Calculations were also performed on a number of push-pull ethylenes whose experimental properties were reported in the chemical literature in order to test the soundness of the conclusions from theoretical approaches. The physical properties calculated for the latter molecules were compared with known experimental values, in order to check the predictive ability of the theoretical approaches employed. Geometrical features and torsional barriers in solution are satisfactorily reproduced. Results were obtained with different basis sets, second-order Moller-Plesset theory, in order to perform comparisons at different theoretical levels with a view to carrying out calculations in larger molecular systems. The widest range of comparisons between calculated values for the different molecules were carried out at the HF/6-31G*//HF/6-31G* level. The origin of the torsional barrier for isomer interconversion as a function of the electronic properties of these molecules is discussed, in particular by examining the polarized character of the exo double bond. The role of the lone pairs of the nitrogen atoms in the push-pull mechanism is investigated, also in competition with an unsaturated bond within the ring. The different conjugation patterns that can be exploited within these molecules is examined within the donor-acceptor model and Natural Bond Orbital (NBO) theory. Empirical correlations are proposed in order to estimate dipole moments and absorption wavelengths for the family of push-pull olefins.

Author(s): R. Benassi, C. Bertarini, E. Kleinpeter and F. Taddei
Title: Exocyclic push-pull conjugated compounds. Part 2. The effect of donor and acceptor substituents on the rotational barrier of push-pull ethylenes
J. Mol. Struct. (Theochem.) Vol. 498, No. 1-3, p. 217-225 (2000); ISSN: 0166-1280; CODEN: THEODJ

keywords: push-pull ethylenes; push-pull compounds; rotational barrier; multiconfigurational approach; electronic properties; conformations
Abstract:
The energy of the rotational barriers and electronic structure of the transition state in substituted ethylenes are discussed in the light of the results obtained from different theoretical MO ab initio approaches. The 6-31G* basis set at Hartree-Fock (HF) level and with second-order Moller-Plesset perturbation theory (MP2) was employed, critical points were localized through Full geometry relaxation and characterized by vibrational analysis. A multiconfigurational approach (MCSCF) with different active spaces was also employed. For alkenes the correct rotational transition state is obtained only from the MCSCF approach, whereas for push-pull olefins the HF approach with correlation corrections at MP2 level provides correct answers for the internal rotation around C(sp(2))-C(sp(2)) bonds. The choice is more critical when only acceptor or donor groups are present, especially when change of hybridization occurs at the atoms at the edges of the C-C bond in the critical points.

Author(s): K. Mohanalingam, P.C. Ray and P.K Das
Title: First hyperpolarizabilities of push-pull olefins measured by the hyper-Rayleigh scattering technique
Synth. Metals Vol. 82, No. 1, p. 47-51 (1996); ISSN: 0379-6779; CODEN: SYMEDZ

keywords: Hyper-Rayleigh scattering; push-pull olefines; bond length alternation; first hyperpolarizability; push-pull ethylenes; butadiene; Rayleigh scattering; electromagnetic wave polarization; chemical bonds; computational methods; correlation methods; first hyperpolarizability; Hyper Rayleigh scattering
Abstract:
First hyperpolarizabilities of a series of donor-acceptor substituted ethylenes and butadienes have been measured using the hyper-Rayleigh scattering technique. Keeping the donor group fixed as dimethylamino, the second-order nonlinear coefficient b in these aliphatic systems has been measured and is shown to increase as a function of the acceptor strength with the exception of the cyano group. b values of the substituted butadienes are correlated with their bond length alternation parameter (dr) obtained from semi-empirical calculations. It is shown that even in these small push-pull olefins, it is possible to generate a variety of ground state structures by choosing a suitable acceptor with a fixed donor.

Author(s): K. Mohanalingam, M. Nethaji and P.K. Das
Title: Second harmonic generation in push-pull ethylenes: Influence of chirality and hydrogen bonding
J. Mol. Struct. Vol. 378, No. 3, p. 177-188 (1996); ISSN: 0022-2860; CODEN: JMOSB4

keywords: hydrogen bonding; chirality; second harmonic generation; push-pull ethylenes
Abstract:
The effect of chiral substituents and hydrogen bonding functional groups on the microscopic and macroscopic second-order non-linearities in some donor-acceptor substituted ethylenes has been investigated. It appears that extensive intramolecular and intermolecular hydrogen bonding helps to improve both the microscopic hyperpolarizability (b) as well as the powder second harmonic generation (SHG) efficiency in these compounds. The substitution of the chiral a-methylbenzylamine donor guarantees a non-centrosymmetric structure. Cocrystallization with triphenylphosphine oxide (TPPO) does not appear to yield better SHG efficiency in the a-methylbenzylamine substituted ethylene compound which has an extended hydrogen bonding network.

Author(s): K. Mohanalingam and P.K. Das
Title: First order hyperpolarizabilities of push-pull olefins
Indian J. Chem. Vol. 31A, No. 8, p. 518-525 (1992); ISSN: 0376-4710; CODEN: IJCADU


Abstract:
In this paper we have reviewed, in brief, the second order polarizabilities of p-conjugated systems, viz., olefins having donor acceptor substituents. Results from our laboratory as well as other groups working in this area have been considered, and a general trend seems to be emerging. Trends in future design and modification of polarized olefinic compounds for a wide range of applications have been discussed.

Author(s): K. Mohanalingam, P.K. Das and S. Rajappa
Title: Second harmonic generation in some donor-acceptor ethylenes
Spectrochim. Acta Vol. 48A, No. 11-12, p. 1647-1656 (1992); ISSN: 0584-8539; CODEN: SAMCAS


Abstract:
We report the absorption spectra, oscillator strengths, ground state and excited state dipole moments, and molecular second order polarizability coefficients (bCT) due to donor-acceptor charge transfer in four trisubstituted ethylenes, namely 1,1-bis(dimethylamino)-2-nitroethylene, 1,1-bispyrolidino-2-nitroethylene, 1,1-bispiperidino-2-nitroethylene and 1,1-bismorpholino-2-nitroethylene. The results are compared with that of trans-N,N-dimethylamino-nitroethylene, which has a large bCT. The powder second harmonic generation (SHG) intensity of all these molecules is also measured and only 1,1-bispiperidino-2-nitroethylene is found to possess an efficiency of 20 % of that of urea under the same conditions. The SHG efficiency of this compound and deficiency in the other molecules in the powdered state is discussed in terms of their arrangements in the unit cell. The crystal structure of the active molecule is also presented and the structure-property relationship is critically examined in all these molecules.

Author(s): R.R. Pappalardo, E.S. Marcos, M.F. Ruiz-Lopez, D. Rinaldi and J.-L. Rivail
Title: Solvent effects on molecular geometries and isomerization processes: A study of push-pull ethylenes in solution
J. Am. Chem. Soc. Vol. 115, No. 9, p. 3722-3730 (1993); ISSN: 0002-7863; CODEN: JACSAT


Abstract:
A detailed study of enamines substituted (H₂NC(H)=C(H)R) by an electron acceptor group (R = NO₂, CN, CHO) in solution has been performed by using the self-consistent reaction field (SCRF) approach. The solvent effects on the E-Z equilibrium as well as on the barriers to internal rotation are in agreement with the known experimental data. Consideration of the electronic wave function allows a detailed analysis of the solvent effects. The polarization of the solute under the influence of the solvent as well as the modifications of its geometry are far from being negligible. Preliminary attempts to estimate electron correlation effects have also been evaluated, and they appear less important than the former effects.

Author(s): R.R. Pappalardo, M.F. Ruiz-Lopez, E.S. Marcos, D. Rinaldi and J.-L. Rivail
Title: Theoretical study of simple push-pull ethylenes in solution
J. Phys. Org. Chem. Vol. 4, No. 3, p. 141-148 (1991); ISSN: 0894-3230; CODEN: JPOCEE


Abstract:
The influence of solvation on the Z - E isomerization process of three representative molecules of simple push-pull ethylenes [H₂N(H)C1=C2(H)R = NO₂, COH and CN] derived from aminoethylene was investigated by means of RHF-SCF ab initio calculations at the 3-21 + G level. Solute-solvent interactions were modelled by a cavity model. The shape of the cavity is based on electronic isodensity surfaces. By using an ellipsoidal cavity very close to the isodensity surface, the perturbation due to the solvent takes an analytical form which is incorporated into the Hartree-Fock equations and leads to efficient quantum chemical computations. The polarization of the solutes under the influence of the solvent is noticeable and was analysed in detail. Similarly, the barriers to internal rotations are substantially modified by the solvent: the barrier around the CC double bond is appreciably decreased in the thermal mechanism whereas its lowering is less important in the anionic mechanism; in contrast, the barrier around the C-1N bond is slightly increased. The variation of the barriers with the nature of the acceptor group is fairly well reproduced by the computations. The electronic structure of the push-pull ethylene molecules and the modifications of this structure under the influence of the solvent are analysed in detail.

Author(s): A. Abbatto, S. Bradamante, N. Capri, H.S. Rzepa, D.J. Williams and A. White
Title: Diheteroarylmethanes. Part 6. Probing the electron-withdrawing rank of heteroaryl groups by conformational studies of push-pull ethylenes. Isolation of NH-enamine tautomers of a,a-diheteroarylacetaldehydes (Heteroaryl = 2-Benzoxazolyl, 2-Benzothiazolyl)
J. Org. Chem. Vol. 61, No. 5, p. 1770-1778 (1996); ISSN: 0022-3263; CODEN: JOCEAH


Abstract:
Enamines and enol ethers substituted in the b-position by the 2-benzoxazolyl and 2-benzothiazolyl group have been obtained by condensing dimethylformamide dimethyl acetal and ethyl orthoformate, respectively, with bis(2-benzoxazolyl)methane and bis(2-benzothiazolyl)methane. A dynamic NMR and semiempirical (PM3) investigation on rotational energy barriers has been carried out in order to rank the electron-withdrawing capacity of the heterocyclic rings. The NMR-based evaluation of the energy barriers corresponding to the rotation along the enaminic double bond has shown that the -electron-withdrawing power of benzothiazole is larger than that of benzoxazole, in full accord with previously obtained charge demand values based on ¹³C and ¹⁵N -charge/shift relationships. The NMR and the computational approaches have led to consistent results. The X-ray crystal structure of a,a-bis(2-benzothiazolyl)-b-(dimethylamino)ethene shows that only one heteroaryl ring is coplanar with the enaminic double bond, while the second one is twisted by 73 ° relative to such a plane. Moreover, in this case calculations closely reproduce the experimental results. In the calculated transition states corresponding to the rotational process along the enamine double bond, the two heteroaryl groups become coplanar and conjugation develops between the enaminic nitrogen electron pool and both heterocycles. The lower rotational barrier observed in the case of the 2-benzothiazolyl derivatives, with respect to the 2-benzoxazolyl derivatives, is therefore a direct consequence of the higher electron-withdrawing power of the former group. Furthermore, a stabilizing intramolecular nonbonded S···S interaction in the rotational transition state of the benzothiazolyl derivatives is evidenced by the calculations. An unprecedented isolation of the NH-enamine tautomer involving the benzoxazolyl and benzothiazolyl ring in a,a-diheteroacetaldehydes has been performed, confirming these heterocycles as strong electron-withdrawing substituents.

Author(s): T.J. Dwyer, J.E. Norman and P.G. Jasien
Title: Rotational barriers in push-pull ethylenes: an advanced physical-organic project including 2D EXSY and computational chemistry
J. Chem. Educ. Vol. 75, No. 12, p. 1635-1640 (1998); ISSN: 0021-9584; CODEN: JCEDA8

Author(s): D. Lloyd and H. McNab
Title: Vinamidines and Vinamidinium Salze - Beispiele stabilisierter Push-Pull Alkene
Angew. Chem. Vol. 88, p. 496-504 (1976); ISSN: 0044-8249; CODEN: ANCEAD

Author(s): P. Karafiloglou and E.S. Marcos
Title: Investigating the possibility of simultaneously finding an electron-hole and an electron-pair in a molecule: delocalization competition of ionic vs. covalent character, and related effects in push-pull ethylenes
Int. J. Quantum Chem. Vol. 44, No. 3, p. 337-362 (1992); ISSN: 0020-7608; CODEN: IJQCB2


Abstract:
This work examines the possibility of finding an electron-hole and an electron-pair simultaneously in a p-system substituted by an electron-donating (NH₂) and/or electron-withdrawing (NO₂) group. The contributions of various ionic structures are calculated from ab initio SCF-CI wave functions, using a recently developed general multielectron population analysis. The molecules studied are two monosubstituted ethylenes, aminoethylene and nitroethylene, and a disubstituted ethylene, the 2-nitroethenamine (push-pull ethylene) in its two configurational forms. The influence of the NH₂ and/or NO₂ group in delocalization and ionic (vs. covalent) character of the C=C double bond are investigated, along with examining the experimental chemist formalism of electron-pair displacements in several resonance structures. Analysis of mutual dependence of an electron-hole and an electron-pair, at short and long distances, leads to the conclusion that a push-pull p-system can stimulate the simultaneous existence of an electronhole and an electron-pair even for nonvicinal positions. The relationship between the electronpair distributions and contributions of the corresponding structures are also examined; the effects of electronic correlation are analyzed as well.

Author(s): D. Adhikesavalu and K. Venkatesan
Title: Push-pull ethylenes: the structures of 3-(2-imidazolidinylidene)-2,4-pentanedione (I), C₈H₁₂N₂O₂, and 3-(1,3-dimethyl-2-imidazolidinylidene)-2,4-pentanedione trihydrate (II), C₁₀H₁₆N₂O₂ x 3 H₂O
Acta Crystallogr. Sect. C: Cryst. Struct. Commun. Vol. C39, p. 1044-1048 (1983); ISSN: 0108-2701; CODEN: ACSCEE

Author(s): E. Kleinpeter, M. Heydenreich, S. K. Chatterjee and W.-D. Rudorf
Title: Study of the p-electron distribution in push-pull alkenes by ¹H- and ¹³C-NMR spectroscopy
Phosphorus, Sulfur, Silicon Relat. Elem. Vol. 95-96, No. 1-4, p. 387-388 (1994); ISSN: 1042-6507; CODEN: PSSLEC


Abstract:
The restricted rotation about a partial C,C double bond of push-pull olefines, was studied by dynamic NMR and 2D-EXSY spectroscopy. Since the barrier to C,C rotation cannot be employed to quantify the push-pull effect of these integrated push-pull alkenes (3,4-dihydro-4-oxo-2H-thiins and 2,3-dihydro-4(1H)-pyridones), the ¹³C chemical shift difference Dd(C5,C6) of the carbon atoms of the partial double bond was used to estimate the charge separation. Even smallest variations in the electron-withdrawing effect of the various donor and acceptor substituents along the push-pull moieties were reflected in the ¹³C chemical shift difference Dd(C5,C6) allowing to quantify the push-pull effect of the present compounds.

Author(s): E. Kleinpeter, A. Koch, M. Heydenreich, S.K. Chatterjee and W.-D. Rudorf
Title: Study of the p-electron distribution in push-pull alkenes by ¹H- and ¹³C-NMR spectroscopy. Part 4. The conformation and dynamic behaviour of substituted N-phenyl-2,3-dihydro-4(1H)-pyridones
J. Mol. Struct. Vol. 356, No. 1, p. 25-33 (1995); ISSN: 0022-2860; CODEN: JMOSB4


Abstract:
The ¹H- and ¹³C-NMR spectra of a number of differently substituted N-phenyl-2,3-dihydro-4(1H)-pyridones (integrated push-pull alkenes) were unequivocally assigned by means of a whole arsenal of 1D and 2D NMR spectroscopic methods. From the extracted NMR parameters and the results of accompanying quantum chemical calculations the preferred conformation of the compounds studied was found to be half-chair with the 1- and 2-substituents in pseudo-axial and axial conformations, respectively. By means of dynamic ¹³C-NMR spectroscopy a dynamic process present was studied (restricted N-aryl rotation); the barriers to rotation were determined approximately at the coalescence temperature and in one case (1d) by complete line-shape analysis (CLSA). The dependence of the barrier to C,N rotation on the electron density polarization along the push-pull moiety (push-pull character) is discussed critically.

Author(s): G. Fischer, W.-D. Rudorf and E. Kleinpeter
Title: Study of the distribution of p-electrons in push-pull alkenes by ¹H- and ¹³C-NMR spectroscopy - I
Magn. Reson. Chem. Vol. 29, No. 3, p. 212-222 (1991); ISSN: 0749-1581; CODEN: MRCHEG


Abstract:
Push-pull alkenes with variable structure were investigated with respect to the influence of the different substituents at the central C,C double bond on the dynamic behaviour of this type of compound. ¹H- and ¹³C-NMR spectroscopic investigations were carried out for ketene-S,S-, -S,N- and -N,N-acetals. HMO calculations were employed to discuss the related p-electron density distributions.

Author(s): E. Kleinpeter, St. Thomas, G. Uhlig and W.-D. Rudorf
Title: Study of the distribution of p -electrons in push-pull alkenes by ¹H- and ¹³C-NMR- spectroscopy - II
Magn. Reson. Chem. Vol. 31, No. 8, p. 714-721 (1993); ISSN: 0749-1581; CODEN: MRCHEG

keywords: 13C chemical shifts; incremental system; semi-selective INEPT; E-Z isomerism; s-cis-s-trans isomerism; restricted C-C rotation; restricted C-N rotation
Abstract:
A wide variety of push-pull alkenes were studied by means of variable-temperature ¹H- and ¹³C-NMR spectroscopy with respect to the configuration/conformation and the barriers to rotation about partial C-C and C-N double bonds. For the assignment of the ¹³C-NMR spectra especially the semi-selective INEPT pulse sequence and an incremental system for estimating the ¹³C chemical shift values of aromatic carbon atoms proved useful. The influence of thioether, sulphone and sulphoxide moieties in the acceptor part of the push-pull system on the p-electron distribution is critically considered.

Author(s): E. Kleinpeter, M. Heydenreich, S. K. Chatterjee and W.-D. Rudorf
Title: Study of the distribution of p-electrons in push-pull alkenes by ¹H- and ¹³C-NMR spectroscopy - III. The conformation of 3,4-Dihydro-4-oxo-2H-thiins
Magn. Reson. Chem. Vol. 32, No. 8, p. 473-479 (1994); ISSN: 0749-1581; CODEN: MRCHEG

keywords: conformation; p-bond polarization; force field calculations; HMQC; HMBC; push-pull alkenes
Abstract:
The ¹H- and ¹³C-NMR spectra of a variety of differently 2,5,6-trisubstituted 3,4-dihydro-4-oxo-2H-thiins (integrated push-pull alkenes) were unequivocally assigned by means of a wide variety of 1D and 2D NMR spectroscopic methods. The NMR parameters thus obtained, together with the results of accompanying force-field calculations, proved useful in determining the preferred ring conformation of 3,4-dihydro-4-oxo-2H-thiin (half-chair). Additionally, the ¹³C chemical shift difference, Dd(C-5,C-6), could be employed to indicate the degree of bond polarization of the partial C-5-C-6 double bond (push-pull character); the barrier to rotation, otherwise used to estimate this parameter characterizing the push-pull alkenes, cannot be applied owing to the ring fusion. Interestingly, NH₂ proved less effective in C-5,C-6 bond polarization than NHPh.

Author(s): E. Kleinpeter, M. Heydenreich, J. Woller, G. Wolf, A. Koch and G. Pihlaja, K. Kempter
Title: Configuration and stereodynamics of exo/endo-isomeric push-pull alkenes of pentadiene structure
J. Chem. Soc., Perkin Trans. 2, p. 1877-1888 (1998); ISSN: 0300-9580; CODEN: JCPKBH

Author(s): S.S. Elmorsy, O.M.O. Habib and M.A. Metwally
Title: Synthesis of novel derivatives of 4-arylideno[3,4-B]-pyran, pyridine- and pyrazolo-, triazolo-, tetrazolo[1,5-A]-pyrimidines
An. Quim. Vol. 89, No. 7-8, p. 711-713 (1993); ISSN: 0365-4990; CODEN: ANQUBU


Abstract:
2-Arylideneindan-1,3-dione (2a,b) undergoes Michael reaction with ethyl cyanoacetate, malononitrile, cyanoacetamide to give compounds 3a, b - 5a, b. On the other hand, treatment, of 1,3-indandione 7 with benzylidene ethylcyanoacetate and benzylidene malononitrile gave 3a and 4a, respectively. Reaction of 3-amino-phenyl-2-pyrazolin-5-one, 3-amino-1,2,4-triazole and 5-aminotetrazole monohydrate with 2a afforded compounds 7, 8 and 9. The structures of the hitherto unknown ring systems have been confirmed by IR and PMR spectral data.

Author(s): G. Bourhill, B.G. Tiemann, J.W. Perry and S.R. Marder
Title: Effect of aromaticy on the second hyperpolarizability of conjugated donor-acceptor molecules
Mol. Cryst. Liq. Cryst.: Nonlinear Optics Vol. 10, No. 1-4, p. 49-60 (1995); ISSN: 1058-7268; CODEN: MCLOEB


Abstract:
The second hyperpolarizabilities, g, of a series of conjugated donor-acceptor molecules, with varying donor and acceptor strengths, containing diene, triene, phenyl and styryl bridges were measured, in solvents of varying polarity, by third harmonic generation. The g values for chromophores containing phenyl or styryl bridges, and their solvent dependence, correspond to a lower degree of neutral/charge-transfer mixing than for polyenes of similar conjugation length. For the phenyl- or styryl-bridged molecules, g increases with increasing donor and acceptor strength, suggesting that even for the julolidino/nitro combination, representing a strong donor/acceptor pair, g has not been maximized. Barbituric acid acceptors, that can gain a degree of aromaticity upon polarization, on a phenyl-containing bridge, lead to g values that are enhanced relative to analogous molecules with moderately strong acceptors, such as dicyanovinyl. The indanedione acceptor, whose conjugation length may increase upon polarization, also leads to large g values.

Author(s): S.R. Marder, B.G. Tiemann, A. Friedli, E. Yang and L.-T. Cheng
Title: Large first hyperpolarizabilities of push-pull polyenes with strong acceptors
Mol. Cryst. Liq. Cryst.: Nonlinear Optics Vol. 9, No. 1-4, p. 213-221 (1995); ISSN: 1058-7268; CODEN: MCLOEB


Abstract:
The molecular first hyperpolarizability, b, of a series of conjugated donor-acceptor molecules, containing N,N'-diethylbarbituric acid or indandione based acceptors was measured, by electric-field-induced-second-harmonic-generation (EFISH). The b values for chromophores containing N,N'-diethylbarbituric acid or indandione based acceptors are large relative to those containing nitrophenyl acceptors, but significantly smaller than those containing N,N'-diethylthiobarbituric acid acceptors, examined previously.

Author(s): S. Juršenas, A. Grruodis, G. Kodis, M. Chachisvilis and L. Valkunas
Title: Optical properties of polar molecular compounds derivatives of dimethylaminobenzylidene 1,3-Indandione (DMABI)
Liet. Fiz. Zh. Vol. 34, No. 4, p. 361-369 (1994); ISSN: 1392-1932; CODEN: LFZUE7
Lith. J. Phys. Vol. 34, No. 4, p. 361-369 (1994);

Abstract:
Spectroscopic, polarization and kinetic properties of 2-n dimethylamine-benzylidene-1,3-indandione (DIMABI) crystals and films are investigated. Specific visible fluorescence bands at 620 nm, 668 nm, and 715 nm characteristic to DMABI films and CT and p modifications of the crystals, respectively, are attributed to self-trapped excited molecular states (S_1f, S_1a, and S_1b). The lifetime of S₁ exciton is directly measured for a crystals t = 7 * 10^-9 s and for b crystals t = 15 * 10^-9 s. With the increase of excitation intensity the onset of non-linear bimolecular annihilation of S₁ excitons is found. The bimolecular annihilation rate constant g = 5 * 10^-10 cm³/s for a modification is estimated from the picosecond state fluorescence kinetics. The characteristic relaxation time of S_1f state for a modification at high excitation intensities is obtained to be less than 3 * 10^-11 s. The strong polarisation dependence of the fluorescence of films and crystals is discovered. Different spectral peculiarities of S₁ state polarization correlate to the build up of DMABI films and crystals and confirm the assumption of characteristic exciton bands S_1f, S_1a and S_1b being present.

Author(s): E.M. Afsah, H.A. Etam, W.S. Hamama and A.F. Sayed Ahmed
Title: Condensation of 2-arylidene-1,3-indandiones with antipyrine and indole
Pharmazie Vol. 50, No. 8, p. 567-569 (1995); ISSN: 0031-7144; CODEN: PHARAT

Author(s): S.A.M. Osman, N.M. Yousif and A.G. Hammam
Title: Some reactions with 2-arylidene-1,3-indandiones and related derivatives of antibacterial activities
Egypt. J. Chem. Vol. 31, No. 2, p. 727-734 (1988); ISSN: 0367-0422; CODEN: EGJCA3

Author(s): E. Gudriniece, G. Vanags, A. Strakov and O. Neiland
Title: The sulfonation of b-diketones - VI. Derivatives of 1,3-indanedione-2-sulfonic acid
J. Gen. Chem. USSR Vol. 29, p. 1863-1867 (1959); ISSN: 0022-1279; CODEN: JGCHA4
Zh. Obshch. Khim. Vol. 29, p. 1893-1897 (1959); ISSN: 0044-460X; CODEN: ZOKHA4
keywords: 2,2-dichloro-1,3-indandione; 2,2-dibromo-1,3-indandione; longest absorption maximum of the anion of 1,3-indandione at 425 nm

Author(s): B.P. Bespalov, A.G. Abolin and V.G. Rumyantsev
Title: Reaction of g-Pyrones with 1,3-bis(dicyanomethylene)indane
Chem. Heterocyclic Comp. Vol. 21, No. 5, p. 501-506 (1985); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 21, No. 5, p. 603-608 (1985); ISSN: 0132-6244; CODEN: KGSSAQ

Abstract:
The condensation of g-pyrones with 1,3-bis(dicyanomethylene)indane leads to the corresponding deeply coloured 2-(pyran-4-ylidene)-1,3-bis(dicyanomethylene)indanes. The reaction of the latter with primary aliphatic or aromatic amines leads to replacement of the pyran oxygen by an amino group. The resulting compounds are zwitterions and possesses dichroic properties. The IR and UV spectra, and also the dichroic spectra of the compounds obtained in a liquid crystal are given. A qualitative explanation of the nature of the absorption bands of these compounds in the visible region of the spectrum is presented.

Author(s): G.W. Buchanan, A.B. Driega and C.I. Ratcliffe
Title: Solution and solid phase ¹³C-NMR studies of cyclic and acyclic 1,2-dialkoxybenzenes and their mononitro derivatives
Magn. Reson. Chem. Vol. 31, p. 1094-1095 (1993); ISSN: 0749-1581; CODEN: MRCHEG

keywords: 13C-NMR; solid state NMR; CP/MAS; dioxygenated benzenes
Abstract:
¹³C-NMR chemical shifts are reported for 1,2-dimethoxybenzene (veratol) and related benzodioxane, benzodioxepane and benzodioxenane systems and their 4-nitro derivatives in solution and in the solid state. Results are discussed in terms of the stereoelectronic influence of substituents.

Author(s): C.N. Robinson and C.C., jr. Irving
Title: Carbon 13-NMR chemical shift-substituent effect correlations in p-substituted 5-benzylidenebarbituric acids and 2-benzylidene-1,3-indandiones
J. Heterocyclic Chem. Vol. 16, p. 921-923 (1979); ISSN: 0022-152X; CODEN: JHTCAD


Abstract:
Excellent correlations have been observed between s+ constants and the ¹³C-NMR chemical shifts of several of the carbon atoms of 5-arylidenebarbituric acids and of 2-arylidene-1,3-indandiones.

Author(s): N.F. Eweiss
Title: Synthesis of Heterocycles. Part V. (1). The synthesis of substituted Indenopyridines
J. Heterocyclic Chem. Vol. 19, p. 273-277 (1982); ISSN: 0022-152X; CODEN: JHTCAD


Abstract:
2-Arylmethylene-1-indanones (I) and 2-arylmethylene-1,3-indandiones (VII) react with active methylene compounds in the presence of ammonium acetate as a basic catalyst to afford substituted pyridines. The postulated routes to the formation of the reported compounds are given.

Author(s): E. Haslinger and P. Wolschann
Title: ¹³C-NMR spectra of electronically neutral organic Lewis acids
Bull. Soc. Chim. Belg. Vol. 86, No. 12, p. 907-915 (1977); ISSN: 0037-9646; CODEN: BSCBAG


Abstract:
The ¹³C-NMR spectra of a number of derivatives of the cyclic acylal of malonic acid and of dimethylbarbituric acid are reported. These compounds contain an electron poor polarized carbon-carbon double bond and act therefore, as Lewis acids.

Author(s): H.C. Scarborough and W.A. Gould
Title: The reaction of urea with cyclic 1,3-dicarbonyl and other active hydrogen compounds
J. Org. Chem. Vol. 26, p. 3720-3723 (1961); ISSN: 0022-3263; CODEN: JOCEAH


Abstract:
A number of 2-carbonyl cyclic 1,3-dicarbonyl compounds have been prepared by the reaction of urea and cyclic 1,3-dicarbonyl compounds. Other active methylene compounds failed to give simple carbonyl derivatives.

Author(s): E.Y. Gudriniece, P.V. Pastors and A.F. Ievin'sh
Title: Condensation of 1,3-indandione with malononitrile
Dokl. Chem. (Engl. Transl.) Vol. 204, No. 4, p. 471-472 (1972); ISSN: 0012-5008; CODEN: DKCHAY
Dokl. Akad. Nauk. SSR, Ser. Khim. Vol. 204, No. 4, p. 874-875 (1972); ISSN: 0366-8665; CODEN: DASKAJ

Author(s): A.J. Fatiadi
Title: New applications of malononitrile in organic chemistry. Part I
Synthesis, No. 3, p. 165-204 (1978); ISSN: 0039-7881; CODEN: SYNTBF


Abstract:
Recent applications of malononitrile in organic chemistry are reviewed; an overview of the chemistry of substituted malononitriles is also included. New trends, mechanisms and synthetic methods employing malononitriles are discussed. Among other topics, this survey includes new information on malononitrile dimers and trimers, new Knoevenagel and Michael condensation reactions, reactions with cyclic polyketones, quinones, sulfur and organometallic compounds, and the synthesis of new heterocycles, pesticides, charge-transfer complexes, and solvatochromic dyes.

Author(s): A.J. Fatiadi
Title: New applications of malononitrile in organic chemistry. Part II
Synthesis, No. 4, p. 241-282 (1978); ISSN: 0039-7881; CODEN: SYNTBF

Author(s): K. Bello, J. Griffiths, P.P. de Wit and E.W.P. Erdhuis
Title: Facile irreversible thermochromism of a near-infrared azamethine chromophore
J. Chem. Soc. Chem. Commun., p. 1031-1032 (1993); ISSN: 0022-4936; CODEN: JCCCAT


Abstract:
The near-infrared azamethine chromophoric system 1 show a pronounced colour change on heating, which is due to a facile disrotatory electrocyclic reaction followed by loss of hydrogen cyanide, giving the intense blue chromophore 2.

Author(s): K. Bello, L. Cheng and J. Griffiths
Title: Near-infrared absorbing methine dyes based on Dicyanovinyl derivatives of Indane-1,3-dione
J. Chem. Soc., Perkin Trans. 2, p. 815-818 (1987); ISSN: 0300-9580; CODEN: JCPKBH

Title: Dense ductile platinium-group metal coatings on other metals
(Degussa vorm. Roessler) Brit. Pat. Appl. GB 990174, (28.04.1965); Patent Class.: C23c
CODEN: BAXXDU
keywords: mono-substitution on 1,3-diketones (acetylacetonate, 1,3-indandione) with malononitrile
corresponding patent CH 415228

Inventor(s): S. Horie, M. Nagata, J. Nakano and H. Sato
Title: Electrophotographic light-sensitive material comprising a charge-generating material and a charge-transporting material
(Fuji Photo Film Co., Ltd.) US Pat. Appl. US 4,469,768, (04.09.1984); Patent Class.: G03G5/06B3B; G03G5/06D2D; G03G5/06D2F; G03G5/06D4D; G03G5/06H2B2
CODEN: USXXDP

corresponding patent: JP1606582C, JP2025502B, JP57204550; DE 3,222,024

Abstract:
An electrophotographic light-sensitive material with an electrophotographic light-sensitive layer containing a charge-generating material and a charge-transporting material is described. The material is characterized in that the charge-generating material is a compound represented by the general formula (I) or (II): (I), (II) (wherein the symbols are the same as defined in the claims).

Inventor(s): P.R. Varanasi, K-Y.A. Jen, K.Y. Wong and R.M. Mininni
Title: 1,1-Vinyl substituted nonlinear optical materials
(Enichem S.p.A.) US Pat. Appl. US 5,514,799, (07.05.1996); Patent Class.: G02F1/35; G02F1/361, G02F1/361D2, G02F1/361F, G02F1/361F2, G02F1/361F4, C07D333/36, C07C225/22, C07D239/60, C07D295/14A2, C07D333/22, C07D333/24, C07D409/06, C07D409/14, C07D495/04
CODEN: USXXDP

corresponding patents: JP 7,173,116; EP 0,637,774

Abstract:
Nonlinear optical compounds having structures with delocalized resonance configures corresponding to: wherein A1 and A2 are independently selected from electron withdrawing moieties; R1 and R2 are independently selected from aromatic rings, heteroaromatic rings and fused ring systems consisting of two or three aromatic or heteroaromatic rings; n and m are integers from one to five, and D1 and D2 are independently selected from hydrogen, electron donating groups and polymer attachment groups, with the proviso that at least one of D1 and D2 is an electron donating group. Polymers blended with, cured with, or having pendant side chains of the disclosed nonlinear optical materials and exhibiting second order nonlinear optical properties are also disclosed.

Author(s): A. Beck, R. Gompper, K. Polborn and H.-U. Wagner
Title: Bi[1,3-bis(dicyanmethylen)-indan-2-yliden] - ein Ethylenderivat mit extrem starker Verdrillung der C=C-Bindung
Angew. Chem. Vol. 105, No. 9, p. 1424-1427 (1993); ISSN: 0044-8249; CODEN: ANCEAD
Angew. Chem. Int. Ed. Engl. Vol. 32, No. 9, p. 1352-1354 (1993);

Author(s): A. Beck, R. Gompper, K. Hartmann and K. Yakogawa
Title: Neue Chromogene mit verdrillten p-Elektronensystemen - Über Indigo and "Überindigo"
Chimia Vol. 48, No. 11, p. 492-493 (1994); ISSN: 0009-4293; CODEN: CHIMAD

Author(s): V. Khodorkovsky, A. Ellern and O. Neilands
Title: A new strong electron acceptor. The resurrection of 2,2'-Biindanylidene-1,3,1',3'-tetraone (BIT)
Tetrahedron Lett. Vol. 35, No. 18, p. 2955-2958 (1994); ISSN: 0040-4039; CODEN: TELEAY

Author(s): R. Gompper, K. Hartmann, R. Kellner and K. Polborn
Title: Bis(dicyanmethylen)- and Bis(cyanimino)-Derivate des Indigos and Thioindigos
Angew. Chem. Vol. 107, No. 4, p. 531-534 (1995); ISSN: 0044-8249; CODEN: ANCEAD

keywords: Farbstoffe; Indigoderivate; Thioindigoderivate

Author(s): J.-M. Adam, P. Sutter and T. Winkler
Title: Malononitrile, a synthetic tool for new chromophoric systems
Chimia Vol. 48, p. 505-507 (1994); ISSN: 0009-4293; CODEN: CHIMAD

Author(s): A. Perjéssy and D. Zacharová-Kalavská
Title: Infrared spectra of some derivatives of benzylidene-1,3-indandione and 2-benzyl-3-hydroxyindandione
Collect. Czech. Chem. Commun. Vol. 35, p. 3802-3807 (1970); ISSN: 0366-547X; CODEN: CCCCAK

Inventor(s): W. Baumann
Title: 3-Dicyanomethylidene-2,3-dihydrothiophen-1,1-dioxide derivatives
(Sandoz, Ltd., Basel) US Pat. Appl. US 4281115, (28.07.1982); Patent Class.: C07D333/52 ; C07D409/06; C07D333/60, C09B23/00S, C09B23/04
CODEN: USXXDP

Published under: GB2026528
corresponding patents: AR231993, AT387580B, AT518779, BE877921, BR7904834, CA1140551, CH636116, CH638514, DD145110, DE2929001, ES482926, FR2438045, FR2438655, GB2084153, HK9189, IT1162353, JP1342994C, JP1460314C, JP55034288, JP60186566, JP61005501B, JP63002988B, SG10685G, YU183279, ZA7903851

Abstract:
The present invention relates to disperse dyes containing a group of formula I, (I) in which R1 signifies the atoms necessary to complete an arylene radical, their production and intermediates therefor.

Author(s): E. Haslinger and P. Wolschann
Title: ¹H-NMR spectra and ensuing conformational evidence on carbon-carbon double bonded systems (Electronically neutal Lewis acids - 33)
Org. Magn. Reson. Vol. 9, No. 1, p. 1-7 (1977); ISSN: 0030-4921; CODEN: ORMRBD


Abstract:
The nmr spectra of various derivatives of the cyclic acylal of malonic acid and of dimethylbarbituric acid are described. From the long range coupling constant, conformational evidence on the dihedral angle between the aromatic ring and the diketodioxane ring or the N,N-dimethylbarbituric ring can be derived. The investigated substances show a dependance of the dihedral angle on the aromatic substitution.

Author(s): K.Y. Chu and J. Griffiths
Title: Electronic absorption spectra and application properties of the isomeric 2-(dimethoxybenzylidene)indan-1,3-dione dyes
J. Appl. Chem. Biotechnol. Vol. 28, p. 144-148 (1978); ISSN: 0375-9210; CODEN: JACBBD


Abstract:
The six isomeric 2-(dimethoxybenzylidene)indan-1,3-diones have been prepared and their electronic absorption spectra recorded. The wavelength dependence of the first absorption band on substitution pattern is complicated by steric effects, but the 2,5-dimethoxy-isomer proved to be the most bathochromic, in agreement with Kauffmann's distribution rule. The sublimation transfer-printing, fluorescence and light fastness properties of the dyes on polyester are reported.

Author(s): G., jr. Irick and J.M. Straley
Title: Yellow to red methine dyes derived from 1,3-Indandione
Text. Chem. Color. Vol. 1, No. 13, p. 178-181 (1969); ISSN: 0040-490X; CODEN: TCCOB6


Abstract:
The excellent lightfastness of greenish-yellow methine dyes derived from malonitrile is widely recognized. The purpose of this work was to determine weather lightfast methine dyes could be obtained in shades than yellow. This paper describes novel yellow to red methine dyes prepared by the action of N,N-disubstituted p-aminobenzaldehydes with 1,3-indandione. These dyes have absorption maxima at wavelengths between those of the malononitrile-based dyes and the tricyanovinyl dyes, but their extinction coefficients are greater than those of either dye. These dyes have excellent affinity for cellulose ester and polyester fibres and show very good lightfastness in yellow to orange shades.

Author(s): G., jr. Irick
Title: Reaction of some 1,3-indandione derivatives
J. Chem. Eng. Data Vol. 16, p. 118-221 (1971); ISSN: 0021-9568; CODEN: JCEAAX


Abstract:
Derivatives 2 and 3 of 1,3-indandione having a carbonyl oxygen replaced by a strong electron-withdrawing group (1,3-dioxo-2-indanylidene or dicyanomethylene) were converted to chlorobenzofulvenes by reaction with phosphoryl chloride. The halogens of these chlorobenzofulvenes were displaced by various nucleophiles to produce coloured products. Red to blue methine dyes were obtained by condensation of the methylene groups in both 2 and 3 with aromatic aldehydes. Visible spectra of the coloured products showed that the 1,3-dioxo-2-indanylidene group was a better electron acceptor than the dicyanomethylene group.

Author(s): E.A. Smirnov and A.E. Podorol'skaya
Title: Color Phenomena in 2-Benzylidene-1,3-Indandione derivatives. I.
J. Gen. Chem. USSR Vol. 39, No. 6, p. 1342-1345 (1969); ISSN: 0022-1279; CODEN: JGCHA4
Zh. Obshch. Khim. Vol. 39, No. 6, p. 1373-1377 (1969); ISSN: 0044-460X; CODEN: ZOKHA4

Author(s): E.A. Smirnov and A.E. Podorol'skaya
Title: Color Phenomena in 2-Benzylidene-1,3-Indandione derivatives. II. 2-Salicylidene-1,3-indandiones
J. Gen. Chem. USSR Vol. 39, No. 6, p. 1346-1350 (1969); ISSN: 0022-1279; CODEN: JGCHA4
Zh. Obshch. Khim. Vol. 39, No. 6, p. 1377-1382 (1969); ISSN: 0044-460X; CODEN: ZOKHA4

Author(s): V.F. Kucherov and L.N. Ivanova
Title: Stereochemistry of cyclic compounds. 1,3-Cyclopentenedione in diene synthesis reactions
Dokl. Chem. (Engl. Transl.) Vol. 131, No. 5, p. 357-359 (1960); ISSN: 0012-5008; CODEN: DKCHAY
Dokl. Akad. Nauk. SSR, Ser. Khim. Vol. 131, No. 5, p. 1077-1079 (1960); ISSN: 0002-3264; CODEN: DASKAJ

Author(s): É.Y. Grens and G. Vanags
Title: 4-Cyclopentene-1,3-dione
Dokl. Chem. (Engl. Transl.) Vol. 133, No. 3, p. 829-833 (1960); ISSN: 0012-5008; CODEN: DKCHAY
Dokl. Akad. Nauk. SSR, Ser. Khim. Vol. 133, No. 3, p. 588-591 (1960); ISSN: 0002-3264; CODEN: DASKAJ
keywords: 4-Cyclopenten-1,3-dione; Cyclopent-4-en-1,3-dione; Cyclopentene-3,5-dione; 2-Cylopentene-1,4-dione

Author(s): V.A. Mironov, A.P. Ivanov and A.A. Akhrem
Title: Cyclic unsaturated compounds. Communication 49. 3-sec-Butylidene-1-sec-butyl-1-cyclopentene
Bull. Acad. Sci. USSR, Div. Chem. Sci. Vol. 22, No. 3, p. 570-573 (1973); ISSN: 0568-5230; CODEN: BACCAT
Izv. Akad. Nauk SSR, Ser. Khim. Vol. 22, No. 3, p. 596-599 (1973); ISSN: 0002-3353; CODEN: IASKA6

Author(s): K.A. Bello and J. Griffiths
Title: Azo dyes with absorption bands in the near infrared
J. Chem. Soc. Chem. Commun., p. 1639-1640 (1986); ISSN: 0022-4936; CODEN: JCCCAT


Abstract:
The first example of monoazo dyes absorbing in the near infrared (up to 806 nm in dimethylsulphoxide) have been prepared from 2-(4-amino-2-acetylaminophenylazo)-4-chloro-5-formylthiazoles by condensing the formyl group with suitable electronegative active methylene compounds under base catalysed conditions.

Author(s): J.F.D. Mills and S.C. Nyburg
Title: Thermochromism and related effects in Bixanthylidenes and Bianthronylidenes. II. General observations.
J. Chem. Soc., p. 927-935 (1963); ISSN: 0368-1769; CODEN: JCSOA9

Inventor(s): E.Y. Gudriniece, A.V. Nikitenko and P.V. Pastors
Title: 1,3-Bis(dicyanomethylene)indane
(Riga Polytechnic Institute) USSR Pat. Appl. SU 325,839, (09.02.1972); Otkrytiya, Izobret., Prom. Obraztsy, Tovanye Znaki, Vol. 49 (1972), p. 238; Patent Class.: C07c
CODEN: URXXAF

Abstract cited from Otkrytiya, Izobret., Prom. Obraztsy, Tovanye Znaki Vol. 49, No.7, p. 238: (1972). [ISSN 0007-4020]

Abstract:
1,3-Bis(dicyanomethylene)indane is prepared by treatment of 1,3-indandione with malononitrile and ammonium acetate in boiling ethanol and acidifying to pH 3.0.

Inventor(s): T. Hioki
Title: 1,3-Bis(dicyanomethylene)indane derivative and production thereof
(Sumitomo Chem. Co. Ltd.) Jpn. Kokai Tokkyo Koho JP 1009968, (13.01.1989); Patent Class.: C07C121/64 ; B41M5/26 ; C07C143/78 ; C07C147/107 ; C07C155/03 ; C07C157/09 ; C07D521/00
CODEN: JKXXAF

Abstract:
NEW MATERIAL: A 1,3-bis(dicyanomethylene)indane derivative shown by formula I (R1-R4 are H, alkyl, alkoxy, halogen, nitro, cyano, hydroxy, amino, -A-R or group shown by formula II; A is group shown by formula III, formula IV or formula V; B is group shown by formula VI or formula VII; R, R' and R'' are H, alkyl, aryl, heterocyclic residue or cyclohexyl). EXAMPLE: 1,3-Bis(dicyanomethylene)indane. USE: Useful as an intermediate for synthesizing a dyestuff for optical information recording medium. PREPARATION: An 1,3-indanedione derivative show by formula VIII is reacted with a malononitrile in a solvent such as ethanol or acetonitrile in the presence of an organic base such as mixed solution of piperidine and glacial acetic acid preferably at 40-80 °C to give a compound shown by formula I. 1,3-bis(dicyanomethylene)indane shwoed l_max = 583 and 631 nm (in acetone).

Author(s): J.F.D. Mills and S.C. Nyburg
Title: Thermochromism and related effects in Bixanthenylidenes and Bianthronylidenes. I. Crystal structure analyses.
J. Chem. Soc., p. 308-321 (1963); ISSN: 0368-1769; CODEN: JCSOA9

Author(s): A.J. Fatiadi
Title: Active manganese dioxide oxidations in organic chemistry. Part I.
Synthesis, No. 2, p. 65-104 (1976); ISSN: 0039-7881; CODEN: SYNTBF

keywords: activated Manganese(IV)-oxyde

Author(s): A.J. Fatiadi
Title: Active manganese dioxide oxidations in organic chemistry. Part II.
Synthesis, No. 3, p. 133-167 (1976); ISSN: 0039-7881; CODEN: SYNTBF

keywords: activated Manganese(IV)-oxyde

Inventor(s): T. Suzuki, H. Ono, S. Aramaki, M. Yokoyama and M. Sudo
Title: Photosensitive body for electrophotography
(Mitsubishi Chem. Ind. Co. Ltd.) Jpn. Kokai Tokkyo Koho JP 61063846, (02.04.1986); Patent Class.: G03G5/06; C07D295/14 ; G03G5/04 ; H01L31/08
CODEN: JKXXAF

Abstract:
PURPOSE: To obtain high sensitivity and high durability by providing a photosensitive layer having specific bistetracyano indenylidene compd. on a conductive base. CONSTITUTION: The photosensitive layer containing the bistetracyano indenylidene compound expressed by the formula (X is H, alkyl, alkoxy or acyl amino, Y is H, halogen or nitro, m is 1-4, n is 0, 1) is provided on the conductive base. Such azo compound has two units of charge separation between the tetracyano group and piperazine ring part within the same molecule and therefore said compound contributes to a considerable improvement in the photosensitivity of the photosensitive layer when used in said layer. Since the compound generates charge carriers at high efficiency when the compound absorbs light, the compd. is suitable for the component of the charge generating layer of a lamination type photosensitive body. The photosensitive body which has high photosensitivity and good color sensitivity, decreases the fluctuation of the photosensitivity and electrostatic chargeability in repetitive use and has less photofatigue and excellent durability is thus obtained. The photosensitive body is used for a printer, etc. using a laser, LED, OFT, etc. as a light source in addition to a copying machine.

Inventor(s): S. Maeda, Y. Kurose, Y. Kimura and J. Nakakuki
Title: Methine based compound and optical recording media containing said compound
(Misubishi Chem. Ind. Co. Ltd.) Jpn. Kokai Tokkyo Koho JP 63075065, (05.04.1986); Patent Class.: C09B23/10 ; B41M5/26 ; G11B7/24
CODEN: JKXXAF

corresponding patents: JP2025824C, JP7049529B

Abstract:
NEW MATERIAL: A compound expressed by formula I [R1 and R2 are H, halogen, OH, alkyl, alkoxy, cyano, nitro, alkoxycarbonyl, aryloxycarbonyl, mono--dialkylaminocarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy or aryloxycarbonyloxy; A is residue obtained by removing one H atom of an aromatic ring of a (substituted) aromatic amine]. EXAMPLE: A compound expressed by formula II. USE: An optical recording medium. PREPARATION: A compound formula III is condensed with cinnamic aldehydes expressed by formula IV [R3 and R4 are H, (substituted) 1-20C alkyl, (substituted) aryl, (substituted) allyl or (substituted) cyclohexyl].

Inventor(s): H. Takeshi and A. Tomioka
Title: Methine compounds, their manufacture and optical information recordimg medium containing them
(Sumitomo Chem. Co. Ltd.) Jpn. Kokai Tokkyo Koho JP 1157944, (21.06.1989); Patent Class.: C07C121/48 ; B41M5/26 ; C07C120/00 ; C07C125/06 ; C07C127/19 ; C07C143/72 ; C07C147/06 ; C07C155/03 ; C07C157/09 ; C07D215/12 ; C07D215/18 ; C07D215/40 ; C07D221/10 ; C07D277/42 ; C07D295/14 ; C09B23/00 ; G11B7/24
CODEN: JKXXAF

Abstract:
NEW MATERIAL: The compound of formula I [X is group of formula II, III, etc.; R1-R4 are H, (substituted) alkyl or alkoxy, halogen, nitro, cyano, etc.; R5 and R6 are H, (substituted) alkyl or aryl, etc.; R7 is (substituted) alkyl, alkoxy, etc.; R8 is H, (substituted) alkyl, halogen, etc.; R9-11 are H or alkyl]. USE: An optical information recording medium. It has absorption peak wavelength in a region of 600-800 nm and exhibits high reflectance in a region of 600-870 nm in the state of thin film. PREPARATION: The compound of formula I can be produced by the condensation reaction of a compound of formula IV with a methine compound of formula X-CHO in a solvent (e.g., chloroform) in the presence of a catalyst (e.g., piperidine) at 0-100 °C.

Inventor(s): Y. Matsushima, A. Tomota, A. Kaneko, M. Ishizuka and H. Suzuki
Title: Photochromic compound
(Yamaha Co.) Jpn. Kokai Tokkyo Koho JP 1226835, (11.09.1989); Patent Class.: C07C21/24 ; C07C17/26 ; C07C43/168 ; C07C43/215 ; C07C49/00 ; C07C49/587 ; C07C57/50 ; C07C59/72 ; C07C63/66 ; C07C65/38 ; C07C69/157 ; C07C69/76 ; C07C79/10 ; C07C87/50 ; C07C97/10 ; C07C99/00 ; C07C101/28 ; C07C101/30 ; C07C121/64 ; C09K9/02
CODEN: JKXXAF

Abstract:
NEW MATERIAL: A compound of formulas I and II (ring A is formula III-VI; X is O, S, NR11; R11 is H, alkyl, allyl, aryl; R1 is each group in R11, alkoxy, allyloxy, aralkyl, aryloxy, NH₂; R2-R10 are each group in R11, CF₃, CN, NO₂, alkoxycarbonyl, COOH, acyl, CONH₂ where at least one of R3-R6 is a group other than the groups in R11; Y is each group in R1-R10 except CF3). EXAMPLE: 1,3-Bisdicyanovinyl-2-(2,5-dimethyl-3-thienylvinylidene)indane. USE: A photochromic compound which is improved in long wavelength sensitivity and enables nondestructive reading, thus being suitably used in optical recording, optical storage material, copying material, photosensitive material for printing, optical filter, display material or the like. PREPARATION: A compound of formula VII is subjected to the Knoevenagel reaction to give the compounds of formulas I-II.

Inventor(s): K. Sato, K. Watanabe and S. Kubodera
Title: Thermal transfer dye donating material
(Fuji Photo Film Co., Ltd.) Jpn. Kokai Tokkyo Koho JP 3081192, (05.04.1991); Patent Class.: B41M5/38
CODEN: JKXXAF
keywords: condensation of 1,3-Bis(dicyanomethylene)indane with N-Oxides resulting in N-Methine-dyes, Imino-dyes
Abstract:
PURPOSE: To obtain a thermal transfer dye donating material having strong absorbancy in a near infrared region, low in the absorption of a visible region and excellent in fastness by providing a thermal transfer layer containing a specific thermal transfer dye on a support. CONSTITUTION: A thermal transfer layer containing a thermal transfer dye represented by formula (I) pref. along with a binder is provided on a support. In the formula (I), R1 is a halogen atom, an alkoxy group, an aryloxy group, an acylamino group, an alkoxycarbonylamino group, a sulfonylamino group, a sulfanoyl group, a hydroxyl group, a sulfonyl group or an ureido group, n is an iteger of 0-2, R1 may be same or different when n is 2, R2 and R3 may be same or different and are an alkyl group,an alkoxy group, a halogen atom, an acylamino group, an alkoxycarbonylamino group or an ureido group, R4 and R5 may be same or different and are a hydrogen atom, an alkyl group or an aryl group and X is a cyano group, an acyl group, an alkoxycarbonyl group, a carbamoyl group or a sulfonyl group.

Inventor(s): T. Hioki, K. Kojima and J. Tomioka
Title: Azamethine compounds, process for preparing the same and a medium for recording optical information using such compounds
(Sumitomo Chem. Co. Ltd.) Eur. Pat. Appl. EP 0287377, (14.04.1987); Patent Class.: C07C121/84 ; C07D215/38 ; C07D221/10 ; C07D277/38 ; C07D295/12 ; C07D333/66 ; C07D409/12 ; C07D417/12 ; G11B7/24
CODEN: EPXXDW
keywords: condensation of 1,3-Bis(dicyanomethylene)indane with N-Oxides resulting in N-Methine-dyes, Imino-dyes, Iminoindanylidene derivates of 1,3-Bis(dicycanomethylene)indane
corresponding patents: DE3883583D, DE3883583T, US5028708, US5061796

Inventor(s): T. Hioki, K. Kojima and J. Tomioka
Title: Azamethinyl quinoline derivatives
(Sumitomo Chem. Co. Ltd.) US Pat. Appl. US 5028708, (19.10.1988); Patent Class.: C07C121/84 ; C07D215/38 ; C07D221/10 ; C07D277/38 ; C07D295/12 ; C07D333/66 ; C07D409/12 ; C07D417/12 ; G11B7/24
Klassifikationssymbol (EC) : C07C121/84, G11B7/24B3, C07D215/38, C07D215/40, C07D221/10, C07D277/42, C07D295/12A1, C07D333/66, C07D409/12, C07D417/12
CODEN: USXXDP
keywords: condensation of 1,3-Bis(dicyanomethylene)indane with N-Oxides resulting in N-Methine-dyes, Imino-dyes
corresponding patents: EP0287377, DE3883583D, DE3883583T, US5061796

Abstract:
Azamethine compounds (suitable for use in the recording layer of an optical information recording medium) have the formula: in which X is a group [in which R5 and R6 are the same or are different and each is a hydrogen atom, a substituted or unsubstituted alkyl or aryl group or a cyclohexyl group, or R5 and R6 together form a ring which may contain a hetero atom; R7 and R8 are the same or are different and each is a hydrogen or halogen atom, a substituted or unsubstituted alkyl or alkoxyl, hydroxyl, nitro or cyano group, or a group -A-R or and R and R' are the same or are different and each is a hydrogen atom, a substituted or unsubstituted alkyl or aryl group or a heterocyclic cyclohexyl group), R9 is hydrogen atom or a substituted or unsubstituted alkyl, aryl or heteroaryl group and R10, R11 and R12 are the same are different and each is a hydrogen atom or an alkyl group]; Y is a group C=O, C=C(CN)₂ or SO; R1, R2, R3 and R4 are the same or are different and each is a hydrogen or halogen atom, a substituted or unsubstituted alkyl, alkoxy or amino group, a nitro, cyano or hydroxyl group or a group -A-R or (as defined above); provided that when Y is a group C=C(CN)₂, X is a group. in which R5, R9, R10, R11 and R12 have the meanings defined above; R7 is a substituted or unsubstituted alkyl or alkoxyl group, a hydroxyl group, a halogen atom or a group -O @-R'' (wherein R'' is an optionally substituted alkyl group); and R8 is a hydrogen or halogen atom or a substituted or unsubstituted alkyl or alkoxyl group.

Inventor(s): A. Wagner and J.W. Kessel
Title: Treatment of intestinal helminthiasis with cyclopentene-1,3-diones
(Eastman Kodak Co.) US Pat. Appl. US 3,592,921, (13.07.1971); Patent Class.: A61K27/00; Klassifikationssymbol (EC) : A61K31/12, C07C49/683, C07C49/687, C07C49/697, C07C49/753, C07C79/36K
CODEN: USXXDP

Abstract:
Domestic animals afflicted with intestinal helminthiasis are treated with cyclopentene-1,3-diones having hydrogen or halogen atoms at the 4 and 5 positions and substituted at the 2 position with benzylidene, dihalomethylene, or diaminomethylene radicals. The active agent can be administered in pill or capsule form or as a drench but is preferably incorporated in the feed and / or water supplied to the animal.

Author(s): S. Inayama, K. Mamoto, T. Shibata and T. Hirose
Title: Structure and antitumor activity relationship of 2-arylidene-4-cyclopentene-1,3-diones and 2-arylideneindan-1,3-diones
J. Med. Chem. Vol. 19, No. 3, p. 433-436 (1976); ISSN: 0022-2623; CODEN: JMCMAR


compare: Inayama, S.; Mamoto, K.: p-Hydroxybenzylidene cycloalkene diones, JP 74,108,056 (Sanyo Kokusaka Pulp Co. Ltd.), published 14.10.1974;

Abstract:
A series of 2arylidene-4-cyclopentene-1,3-diones and 2-arylideneindan-1,3-diones, as well as mono- and bis(arylidene substituted) cycloalkanones, was synthesized and examined for antitumor activity against ascites sarcoma-180. All the 2-arylidene-4-cyclopentene-1,3-diones and one arylideneindan-1,3-dione (where the arylidene group was either a hydroxybenzylidene or substituted hydroxybenzylidene) exhibited a high degree of activity. Among both types of 1,3-diones the 3-methoxy-4-hydroxybenzylidene derivatives were found to possess the greatest potency, while all the mono- and bis(arylidene)cycloalkanones were found to be inactive.

Inventor(s): S. Inayama and K. Mamoto
Title: p-Hydroxybenzylidene cycloalkene diones
(Sanyo Kokusaka Pulp Co. Ltd.) Jpn. Kokai Tokkyo Koho JP 74,108,056, (14.10.1974); Patent Class.: 16D21
CODEN: JKXXAF

compare: Inayama, S.; Mamoto, K.; Shibata, T.; Hirose, T.: J. Med. Chem. 19, 1976, 433-436.

Inventor(s): Walter Rumpel
Title: Verfahren zur Herstellung von Divanillyden-Cyclohexanon
(Anton von Waldheim, Pharmazeutische Fabrik, Wien) Austrian Pat. AT 180258, (15.05.1954)
CODEN: AUXXAK
keywords: condensation of vanilline with cyclohexanone under the influence of sulfuric acid catalysis

Author(s): G. Vanags, B. Fal'kenshtein, I. Ershova, L. Egorova and V. Osipova
Title: Results of investigation of the rodenticidal effect of compounds belonging to the Indandione-1,3 group
Latvijas PSR Zinatnu Akad. Vestis Vol. 217, No. 8 (217), p. 129-137 (1965); ISSN: 0023-8929; CODEN: LZAVAL

Author(s): D. Guillaume and L. Wescott
Title: An NMR study of 1,3-Bis(dicyanomethylene)indane
(1998);


EDUCATION Christian Brothers University, Memphis, Tennessee
Bachelor of Science in Chemistry; Graduation
Date May 1998, GPA 3.0/4.0.
Research: An NMR study of 1,3-bis(dicyanomethylene)indane

Douglas Guillaume worked with Dr. Lyle Wescott of CBU and presented a paper entitled: "An NMR Study of 1,3-bis (dicyanomethylene) Indane."

http://www.cbu.edu/~holmes/Sciences/research.html

Resume:
DOUGLAS B. GUILLAUME
Current Address:
650 East Parkway South, Box 93
Memphis, Tennessee 38104
(901) 321-3667

Permanent Address:
17345 Empress Drive
Greenwell Springs, Louisiana 70739
504) 261-7948

Entry no. 78
Author(s): S.-S. Sun, A.W. Harper, C. Zhang, L.R. Dalton, S.M. Garner, A. Chen, A. Yacoubian and W.H. Steier
Title: Synthesis and characterization of 1,3-Bis(dicyanomethylene)indane (BDMI) derived second order NLO materials
A.K.-Y. Jen, C.Y.-C. Lee, L.R. Dalton, M.F. Rubner, G.E. Wnek and L.Y. Chiang (ed.), Vol. 413, p. 263-268 (1996); Materials Research Socety, Pittsburgh; ISBN: 1-55899-316-9; CODENMRSPDH; Materials Research Society Symposium, Boston, Massachusetts, U.S.A, November 27-December 1, 1995

Materials Research Society Symposium Proceedings (1996), Vol. 413 (Electrical, Optical, and Magnetic Properties of Organic Solid State Materials III), 263-268. "Synthesis and Characterization of 1,3-Bis(dicyanomethylene)indane (BDMI) Derived Second Order NLO Materials," Materials Research Society Symposium Proceedings, Vol. 413,
http://www.usc.edu/dept/materials_science/faculty/dalton-pub.htm

Abstract:
Difunctionalized aminophenylenethienylidene-1,3-bisdicyanomethyleneindane (BDMI) derived second order push-pull chromophores and polymers have been synthesized and characterized. Preliminary studies of doped polymeric composite thin films reveal large SHG signals as well as good chemical and thermal stabilities under poling conditions.

Author(s): S.-S. Sun, C. Zhang, L.R. Dalton, S.M. Garner, A. Chen and W.H. Steier
Title: 1,3-Bis(dicyanomethylene)indane based 2nd NLO materials
Chem. Mater. Vol. 8, No. 11, p. 2539-2541 (1996); ISSN: 0897-4756; CODEN: CMATEX

Author(s): S.-S. Sun, C. Zhang, Z. Yang, L.R. Dalton, S.M. Garner, A. Chen and W.H. Steier
Title: Synthesis and characterization of 1,3-Bis(dicyanomethylidene)indane (BDMI) based nonlinear optical polymers
Polymer Vol. 39, No. 20, p. 4977-4981 (1998); ISSN: 0032-3861; CODEN: POLMAG

keywords: 1,3-bis(dicyanomethylidene)indane; nonlinear optical polymers; electro-optic materials
Abstract:
New polymers containing nonlinear optical chromophores of electron donor-bridge moieties amino-phenylenethienylidene (APT) coupled with a strong electron acceptor 1,3-bis(dicyanomethylidene)indane (BDMI) were synthesised by coupling the aldehydic APT precursor polymers with acceptor BDMI in acetic anhydride. The aldehydic APT precursor polymers were prepared via traditional condensation or radical polymerisation schemes where the aldehydic group of APT was found intact. Thermal stability of these BDMI-based polymers determined by t.g.a. was up to 500 °C depending mainly on the chromophore loading density. The electro-optic coefficient (r33) of 10 pm V-1 was obtained in a 30 % by weight chromophore loading polymer.

Author(s): J. Rommens, M. van der Auweraer, F.C. De ScIryver, D. Terrell and S. Demeutter
Title: Electron transport in 1,3-bis(dicyanomethylene)indanes
J. Phys. Chem. Vol. 100, No. 25, p. 10673-10680 (1996); ISSN: 0022-3654; CODEN: JPCHAX


Abstract:
Upon investigation of the photoconductive properties of polycarbonate doped with 1,3-bis(dicyanomethylene)indanes, a large temperature independent quantum yield for charge generation was observed. The field and temperature dependence of the charge carrier mobility could be analyzed in the framework of the disorder model, developed by Baessler et al. The prefactor mobility was found to be of the same order of magnitude as that observed for hole transport materials with a comparable dipole moment. In the framework of the used disorder model, this relationship would suggest a dependence of the wave function decay constant on the molecular dipole moment. This would result in a material dependence of the prefactor mobility, which has also been found for other charge transport molecules.

Author(s): J. Rommens, M. van der Auweraer, F.C. De Schryver and P.M. Borsenberger
Title: A new class of electron-transport compounds - 1,3-Bis(dicyanomethylene)indanes
Adv. Materials Vol. 7, No. 6, p. 574-576 (1995); ISSN: 0935-9648; CODEN: ADVMEW

Author(s): G. Kodis, V. Gulbinas, L. Valkunas and S. Juršenas
Title: Non-linear luminescence of dimethylaminobenzylidene-1,3-indandione solids
Adv. Mater. Opt. Electron. Vol. 6, No. 5&6, p. 391-394 (1996); ISSN: 1057-9257; CODEN: AMELE7


Abstract:
The origin of the nonlinear anti-Stokes luminescence effect in 4-dimethylaminobenzylidene-1,3-indandione (DMABI) crystals, i.e. the luminescence in the visible spectral region created by IR excitation, was studied by ultrafast pump-probe and luminescence spectroscopy. In contrast with the previously proposed luminescence excitation model based an low-energy exciton annihilation, the luminescence state is excited via two-photon absorption through virtual and real (characterized by 1 ps lifetime) intermediate states. Second-harmonic generation and pulse duration effects on the nonlinear luminescence are discussed. Exciton-exciton annihilation on the manifold of luminescent states was observed at high excitation intensities.

Author(s): G. Kodis, V. Gulbinas, L. Valkunas and S. Juršenas
Title: Nonlinear luminescence of polar dimethylaminobenzylidene-1,3-indandione compounds
Liet. Fiz. Zh. Vol. 36, No. 4, p. 336-339 (1996); ISSN: 1392-1932; CODEN: LFZUE7
Lith. J. Phys. Vol. 36, No. 4, p. 336-339 (1996);

Abstract:
The origin of the nonlinear anti-Stakes luminescence effect in 4-dimethylaminobenzylidene-1,3-indandione (DMABI) crystals, i.e. the luminescence in the visible spectral region created by the IR excitation, was studied by ultrafast pump-probe and luminescence spectroscopy. In contrast to the earlier proposed luminescence excitation model based on the low-energy exciton annihilation, the luminescence state is excited via two-photon absorption through the virtual and real (characterized by 1 ps lifetime) intermediate states. The second-harmonic generation and pulse duration effect on the nonlinear luminescence are discussed. The exciton-exciton annihilation on luminescent states manifold was observed at high excitation intensities.

Author(s): Juršenas, S., Aleksa V., Kovalevskij V. and Valkunas L. Gruodis A.
Title: The vibrational spectrum of N,N-dimethylaminobenzylidene 1,3-indandione
Liet. Fiz. Zh. Vol. 38, No. 2, p. 237-243 (1998); ISSN: 1392-1932; CODEN: LFZUE7
Lith. J. Phys. Vol. 38, No. 2, p. 237-243 (1998);

Abstract:
The IR and Raman spectra of N,N-dimethylaminobenzylidene-1,3-indandione (DMABI) as solids and solutes in various solvents have been recorded in the spectral region of 4000-50 cm^-1. The spectra were compared to ab initio calculations in the B3LYP/6-311G basis set. Having assigned the molecular vibrations, the IR absorption and Raman spectra of the crystal phase were studied and the lattice modes were identified.

Author(s): I. Kaulach and E.A. Silinis
Title: Spectral dependence of magnetic field effect on photoconductivity of dimethylaminobenzylidene 1,3­indandione
Latv. J. Phys. Tech. Sci., No. 3, p. 3-11 (1997); ISSN: 0868-8257; CODEN: LJPSED


Abstract:
Spectral dependence measurement of photocurrent quantum efficiency (b), and influence of external static magnetic field (H = 0 to 6 KOe) on b were performed in 0.9-3.3 eV spectral range in vacuum evaporated layers and multilayer Langmuir-Blodgett films of 4-dimethylaminobenzylidene-1,3-indandione (DMABI). Increase of b up to (1-4) % in an external magnetic field was observed in the range hn > 1.9 eV with expressed threshold of the effect at hn = ca. 1.8 eV. This step-like increase of magnetic field effect is interpreted in terms of magnetic field influence on intersystem crossing of localized intermolecular charge transfer (CT) states according to the Merrifields hyperfine interaction model. It was shown that the dissociation of these CT states into free charge carriers is the main charge carrier photogeneration channel in the DMABI samples within the 1.9-3.3 eV spectral range at room temperatures. A schematic energy diagram of conversion of excited CT states in DMABI samples, explaining magnetic field influence on the charge carrier photogeneration process, is presented.

Author(s): S. Juršenas, A. Gruodis, G. Kodis, M. Chachisvilis, V. Gulbinas and E.A. Silinis
Title: Free and self-trapped charge-transfer excitons in crystals of dipolar molecules of N,N-dimethylaminobenzylidene 1,3-indandione
J. Phys. Chem. B Vol. 102B, No. 7, p. 1086-1094 (1998); ISSN: 1089-5647; CODEN: JPCBFK


Abstract:
In this paper we consider the spectral properties of exciton transitions of N,N-dimethylaminobenzylidene-1,3-indandione (DMABI) films and crystals, which are typical examples of polar molecular compounds. A large dipole moment in the electronic ground state and the considerable change (up to 12 D) of this value by excitation of a free DMABI molecule induce strong polarization of the surroundings, which causes the remarkable self-trapping effects in the crystal. The exciton-phonon coupling value g = 1.87 is estimared for the crystal. Charge-transfer (CT) exciton formation is observed in the absorption and luminescence spectra by analyzing the spectral behavior at various thickness of DMABI films. The CT excitons created along molecular stacks dominate in the spectra of the DMABI crystals. Coexistence of free and self-trapped CT excitons is discovered at elevated temperatures. The exciton band parameters are estimated, and the adiabatic energy potential energy for two self-trapped excitons is suggested. Relaxation paths of shallow short-lived and deeply trapped long-lived self-trapped CT excitons are discussed. Mechanisms of two-photon absorption and photoconduction of DMABI crystals and films are considered.

Author(s): V. Oskaja and G. Vanags
Title: Synthesis of certain 2-arylindanediones-1,3 containing methoxy groups
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 1, p. 87-95 (1962); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): G. Tirzitis, R. Zagats and G. Vanags
Title: Preparation of indandione-1,3 and bindone
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 1, p. 97-101 (1962); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): E. Grens and G. Vanags
Title: MO LCAO calculations and keto-enol equilibrium of b-dicarbonyl compounds
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 3, p. 278-286 (1967); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): F. Grunsberg and A. Arens
Title: Correlation of electronic absorption spectra of arylidencyclopentantriones-1,2,4 and arylidenindandiones-1,3 with s+ - constants
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 4, p. 468-470 (1971); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): P.V. Pastors and E.Y. Gudriniece
Title: Condensations of b-dicarbonyl compounds with malononitrile. V. Reactions between 1,1,3,3-tetracyanoindandimethane and aromatic aldehydes
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 3, p. 355-357 (1973); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): I. Zilniece and A. Ziemanis
Title: High-molecular catalysts in organic synthesis. VII. Condensation of cyclic 1,3-diketones with aromatic aldehydes
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 5, p. 616-619 (1984); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): A.J. Birch and R.J. English
Title: b-Triketones. Part IV. The Chromophore of Calythrone
J. Chem. Soc., p. 3805-3806 (1957); ISSN: 0368-1769; CODEN: JCSOA9

Author(s): A.K. Kiang, H.H. Lee and K.Y. Sim
Title: The structure of Linderone and Methyl-linderone
J. Chem. Soc., p. 4338-4345 (1962); ISSN: 0368-1769; CODEN: JCSOA9

Author(s): F. Merényi and M. Nilsson
Title: Facile preparation of 2-acetyl-cyclopentane-1,3-dione and 2-acetylcyclohexane-1,3-dione
Acta Chem. Scand. Vol. 17, No. 6, p. 1801-1802 (1963); ISSN: 0904-213X; CODEN: ACHSE7

Author(s): M. Nilsson
Title: Preparation of 2-Acetylcyclopent-4-ene-1,3-diones from maleic anhydrides and isopropenyl acetate
Acta Chem. Scand. Vol. 18, No. 2, p. 441-446 (1964); ISSN: 0904-213X; CODEN: ACHSE7

Author(s): S. Forsén and M. Nilsson
Title: Spectroscopic studies on Enols. Part 6. Enolisation and hydrogen bonding in 3-Acetylcyclopentane-1,2,4-triones
Acta Chem. Scand. Vol. 18, No. 2, p. 513-520 (1964); ISSN: 0904-213X; CODEN: ACHSE7

Author(s): C.H. DePuy and E.F. Zaweski
Title: Cyclopentene-3,5-dione
J. Am. Chem. Soc. Vol. 79, p. 3923-2924 (1957); ISSN: 0002-7863; CODEN: JACSAT

keywords: 4-Cyclopenten-1,3-dione; Cyclopent-4-en-1,3-dione

Author(s): C.H. DePuy and E.F. Zaweski
Title: Cyclopentene-3,5-dione. I. Synthesis and properties
J. Am. Chem. Soc. Vol. 81, p. 4920-4924 (1959); ISSN: 0002-7863; CODEN: JACSAT

keywords: 4-Cyclopenten-1,3-dione; Cyclopent-4-en-1,3-dione; 2-Cyclopentene-1,4-dione

Author(s): C.H. DePuy and C.E. Lyons
Title: Cyclopentene-3,5-dione. II. Conversion to Cyclopentadienone
J. Am. Chem. Soc. Vol. 82, p. 631-633 (1960); ISSN: 0002-7863; CODEN: JACSAT

keywords: 4-Cyclopenten-1,3-dione; Cyclopent-4-en-1,3-dione; 2-Cyclopentene-1,4-dione

Author(s): C.H. DePuy and P.R. Wells
Title: Cyclopentene-3,5-dione. III. Reactions of the methylene group
J. Am. Chem. Soc. Vol. 82, p. 2909-2913 (1960); ISSN: 0002-7863; CODEN: JACSAT

keywords: 4-Cyclopenten-1,3-dione; Cyclopent-4-en-1,3-dione; 2-Cyclopentene-1,4-dione

Author(s): C.H. DePuy, R.D. Thurn and M. Isaks
Title: Cyclopentene-3,5-dione. IV. Reactions with brominating agents and with ethanol
J. Org. Chem. Vol. 27, p. 744-748 (1962); ISSN: 0022-3263; CODEN: JOCEAH

keywords: 4-Cyclopenten-1,3-dione; Cyclopent-4-en-1,3-dione; 2-Cyclopentene-1,4-dione

Author(s): G.H. Rasmusson, H.O. House, E.F. Zaweski and C.H. DePuy
Title: 2-Cyclopentene-1,4-dione
Org. Synth. Vol. 42, p. 36-39 (1963);

keywords: 4-Cyclopenten-1,3-dione; Cyclopent-4-en-1,3-dione; Cyclopentene-3,5-dione

Author(s): J. Steigman and L.P. Hammett
Title: The Walden inversion: Configurational effects in the solvolytic reactions of a-Phenylethyl chloride
J. Am. Chem. Soc. Vol. 59, p. 2536-2542 (1937); ISSN: 0002-7863; CODEN: JACSAT

keywords: Tetrabutyl ammonium acetate as source of nucleophilic acetate ions

Author(s): G.S. Bahra, J. Griffiths, W. Healy, V. Millar, S.J. Till and J. Till
Title: Towards a structure-RSA relationship for non-linear optical materials
Materials Research Society Symposium Proceedings Vol. 374 (Materials for Optical Limiting), p. 33-38 (1994 (publ. 1995)); ISSN: 0272-9172; CODEN: MRSPDH


Materials for optical limiting : symposium held November 28 - November 30, 1994, Boston, Massachusetts, USA ; [at the 1995 (i.e. 1994) MRS Fall Meeting] / [Symposium on Materials for Optical Limiting]. Ed.: Robert Crane

Abstract:
Measurements on the reverse saturable absorption (RSA) properties of some polyene dyes are presented. For a series of linear dyes, a correlation is observed between the symmetry of a molecule and its ability to exhibit RSA. To our knowledge, this is the first structure-RSA relationship discovered to date. Certain of these materials have been studied with semi-empirical quantum chemical techniques and the observed structure-RSA relationship is rationalised in terms of the calculated electronic structures. In this paper, we report primarily on some studies we have carried out on the linear dye systems.

Author(s): J. Griffiths, V. Millar and G.S. Bahra
Title: The influence of chain length and electron acceptor residues in 3-substituted 7-N,N-diethylaminocoumarin dyes
Dyes Pigm. Vol. 28, No. 4, p. 327-339 (1995); ISSN: 0143-7208; CODEN: DYPIDX


Abstract:
Several 7-N,N-diethylaminocoumarin dyes with vinylogously extended electron acceptor groups in the 3-position have been prepared by condensing the 3-aldehyde with various active methylene compounds. Structures vary according to both the nature of the electron withdrawing moiety and the length of the conjugation pathway between the 7-amino group and the electron acceptor residue. Dyes with colours ranging from red to cyan have been prepared, and their light absorption properties are discussed in terms of the electron acceptor and the extent of conjugation. Steric factors play a major role in influencing the colour properties, and this was exemplified in one extreme case where lengthening the conjugation chain by one vinyl unit caused a hypsochromic shift due to increased steric interactions. In general, the vinylogous donor-acceptor coumarin dyes were not as fluorescent as the more conventional 7-dialkylaminocoumarins which have a shorter conjugation path between the amino group and the 3-acceptor group. Two cationic dyes have been prepared by condensation of the coumarin aldehyde, with enamines, and these show typical cyanine dye characteristics, with intense long wavelength absorption.

Author(s): K.A. Bello and M.K. Yakubu
Title: Novel monazo disperse dyes derived from 3,5-dibromoaminobenzaldehyde as diazo component
Colourage Vol. 44, No. 1, p. 49-52 (1997); ISSN: 0010-1826; CODEN: COLOBG

keywords: condensation of 1,3-bis(dicyanomethylene)indane with aromatic aldehydes of azo dyes
Abstract:
The synthesis and dyeing properties of the azo dye formed by coupling diazotized 4-amino-3,5-dibromobenzaldehyde (I) to 3-acetamido-N,N-diethylaniline and its subsequent condensation with 4 different active methylene compounds have been studies. Replacement of the two bromo groups of (I) by cyano groups affords another series of dyes with bathochromic shift of ~10 nm relative to the I derivatives. The washfastness of the dyes on polyester is adequate, but their lightfastness properties are quite low.

Author(s): K.A. Bello, C.M.O.A. Martius and I.K. Adamu
Title: Methine dyes formed by condensation of indane-1,3-dione and cyanovinyl analogs with benzaldehydes
J. Soc. Dyers Colour. Vol. 110, No. 7, p. 238-240 (1994); ISSN: 0037-9859; CODEN: JSDCAA


Abstract:
A range of dyes has been synthesised by condensing highly electronegative active methylene compounds derived from indane-1,3-dione with the formyl group of substituted benzaldehydes. The visible absorption spectroscopic properties of the dyes were investigated. In general the dyes provided bright colours, ranging from yellow to blue on synthetic fibres when applied by vapour-phase transfer printing, the prints having reasonable fastness to washing (ISO 3).

Author(s): J. Zhu, A.W. Harper, S.-S. Sun, L.R. Dalton, S.M. Garner and W.H. Steier
Title: Progress towards the translation of large microscopic nonlinearities to large macroscopic nonlinearities in high-mb materials
ACS Symp. Ser. Vol. 695 (Organic Thin Films), p. 258-266 (1998); ISSN: 0097-6156; CODEN: ACSMC8


Organic thin films: structure and applications ; developed from a symposium ... at the 213th national meeting of the American Chemical Society, San Francisco, California, April 13 - 17, 1997 / Curtis W. Frank, ed.

Abstract:
By synthetic modification of a high mb chromophore to defeat electrostatic intermolecular interactions, the electro-optic coefficients were doubled (to 42 pm/V) in comparison to the unmodified analogue. We believe that increasing the hydrodynamic volume of a chromophore is a general method to circumvent chromophore-chromophore interactions, which can lead to large macroscopic nonlinearities.

Inventor(s): L. Descloux and L. Chassot
Title: Haarfärbemittel
(Wella AG, Germany) German Pat. Appl. DE 19852337, (18.05.2000); Patent Class.: A61K7/13
CODEN: GWXXBX

corresponding patents: BR9905364, EP1002516, JP2000143466 (JP00143466), US6231622

Inventor(s): S. Kubodera and K. Sato
Title: Heat transfer dye-providing material
(Fuji Photo Film Co. Ltd.) Jpn. Kokai Tokkyo Koho JP 04173290, (19.06.1992); Patent Class.: B41M5/035 ; B41M5/26
Klassifikationssymbol (EC) : B41M5/40F2
CODEN: JKXXAF

corresponding patents: US5192737

Abstract:
There is disclosed a thermal transfer dye-providing material capable of providing a sharp image having a high density. The dye-providing material includes a support having provided thereon a layer containing a thermally migrating dye, wherein at least one of the dye-containing layer and a layer adjacent thereto contains an infrared-absorbing dye represented by Formula (I), (II) or (III): Formula (I) Formula (II) Formula (III).

Inventor(s): A.K.-Y. Jen, R.M. Mininni, P.R. Varanasi, K.Y. Wong and K.J. Drost
Title: Efficient electron-donating groups for nonlinear optical applications
(Enichem Spa.) Eur. Pat. Appl. EP 602,654, (22.06.1994); Patent Class.: G02F1/35; C07D409/06 ; C07D409/14 ; C07D417/06 ; C07D495/04
Klassifikationssymbol (EC) : G02F1/361, G02F1/361B2, G02F1/361D2, G02F1/361F, G02F1/361F4, C07D333/22, C07D409/06, C07D409/14, C07D417/06, C07D495/04
CODEN: EPXXDW

corresponding patent: JP6228153

Abstract:
Nonlinear optical materials having structures with delocalized resonance configurations corresponding to: or: wherein A is a first electron accepting group, R is pi-conjugated non-centrosymmetric organic moiety; R4 and R5 are independently selected from hydrogen, alkyl moieties and functionalized alkyl moieties; E, F, G and H are members of a saturated or unsaturated five- to ten-membered cyclic ring or two-ring systems having five- to ten-membered rings that are electron donating in nature and E, F, G and H are independently selected from -CH-, -CH2-, O, S, N, Se, Te, and -NR2-, wherein R2 is selected from hydrogen, alkyl moieties and functionalized alkyl moieties; and R1 is selected from alkyl moieties and functionalized alkyl moieties. Polymers blended with or having the disclosed nonlinear optical materials as pendant side chains and exhibiting second order nonlinear optical properties are also disclosed.

Inventor(s): P.P. De Wit, E.W.P. Erdhuisen and J. Griffiths
Title: Liquid crystalline and infrared-sensitive liquid-crystalline polyesters
(Akzo NV) US Pat. Appl. US 5525265, (11.06.1996); Patent Class.: G11B7/00 ; G11B7/24 ; G11B7/26
Klassifikationssymbol (EC) : G11B7/00M4L, G11B7/24, G11B7/24B3
CODEN: USXXDP

corresponding patents: EP0478052, DE69106824D, DE69106824T, ES2067848T, JP4283228

Abstract:
Disclosed are liquid-crystalline and infrared-sensitive liquid-crystalline polyesters for optical data storage, processes for the preparation of the same, and an apparatus comprising an infrared-sensitive liquid-crystalline polyester. Owing to covalently bonded dye the liquid crystalline polyester is infrared sensitive and high concentrations of dye are obtainable, without having detrimental effects on the properties of the liquid-crystalline polyester. This results in a highly sensitive liquid-crystalline polyester for optical data storage. Infrared dyes which are preferably bonded in liquid-crystalline polyester are croconium, squarilium, azo, and azamethine dyes.

Author(s): M. Gozález, N. Martín, C. Segura, J. Garín, J. Orduna, R. Alcalá, C. Sánchez and B. Villacampa
Title: Second-order nonlinear optical properties of tetrathiafulvalene-p-3-(dicyanomethylidene)indan-1-one chromophores
Tetrahedron Lett. Vol. 40, No. 49, p. 8599-8602 (1999); ISSN: 0040-4039; CODEN: TELEAY

keywords: tetrathiafulvalenes; electronic spectra; electrochemistry; non-linear optics
Abstract:
Novel conjugated donor-acceptor chromophores, based on the strong electron donating tetrathiafulvalene moiety and the strong electron-withdrawing 3-(dicyanomethylidene)indan-1-one acceptor, exhibit large second-order optical nonlinearities. The effect of increasing the length of the polyenic spacer on the NLO properties of the new molecules has been studied by using the electric field-induced second harmonic generation (EFISH) method.

Author(s): J.-M. Raimundo, P. Blanchard, P. Frére, N. Mercier, I. Ledoux-Rak, R. Hierle and J. Roncalli
Title: Push-pull chromophores based on 2,2'-bi(3,4-ethylenedioxythiophene) (BEDOT) p-conjugating spacer
Tetrahedron Lett. Vol. 42, No. 8, p. 1507-1510 (2001); ISSN: 0040-4039; CODEN: TELEAY


Abstract:
Replacement of 2,2'-bithiophene by BEDOT in push-pull NLO-phores produces a red shift of the absorption maximum accompanied with a large increase of the quadratic nonlinear optical susceptibility.

Inventor(s): L. Descloux and L. Chassot
Title: Dye compositions, especially for dyeing hair, containing indane derivative compounds
(Wella AG, Germany) US Pat. Appl. US 6231622; Patent Class.: A61K7/13B, A61K7/13D
CODEN: USXXDP

corresponding patents: DE19852337, BR9905364, EP1002516, JP2000143466 (JP00143466)

Abstract:
The dye composition for fibers, especially keratin-containing fibers, contains at least one indane derivative compound of formula I, or a physiologically compatible, water-soluble salt thereof:wherein R1 is hydrogen, a halogen atom, a cyano group, a hydroxy group, a C1- to C4- alkoxy group, a C1- to C6- alkyl group, a nitro group, an amino group, an alkylamino group, a dialkylamino group, a -C(O)H group, a -COOR3 group, a -SO2R3 or a -C(O)CH3 group, wherein R3 is hydrogen, phenyl or a C1- to C6- alkyl group; and R2 is hydrogen, a C1- to C6- alkyl group or a phenyl group.

Inventor(s): S. Kubodera and K. Sato
Title: Heat transfer dye-providing material
(Fuji Photo Film Co. Ltd.) US Pat. Appl. US 5192737, (09.03.1993); Patent Class.: 41M5/035 ; B41M5/26; B41M5/40F2
CODEN: USXXDP

corresponding patent: JP4173290

Abstract:
There is disclosed a thermal transfer dye-providing material capable of providing a sharp image having a high density. The dye-providing material includes a support having provided thereon a layer containing a thermally migrating dye, wherein at least one of the dye-containing layer and a layer adjacent thereto contains an infrared-absorbing dye represented by Formula (I), (II) or (III): Formula (I) Formula (II) Formula (III).

Inventor(s): M. Kato, K. Kato and T. Komamura
Title: Heat developable color photographic material
(Konica K.K.) Jpn. Kokai Tokkyo Koho JP 04 86,658, (19.03.1992); Patent Class.: G03C8/40 ; C09B23/00
CODEN: JKXXAF

Abstract:
PURPOSE: To attain the reading of the information recorded by using longer wavelengths of light than 750 nm by using a compound for which at least one compound of dye imparting supplying materials has an absorption maximum at 400-700 nm, and incorporating a specified compound. CONSTITUTION: This material is a heatdevelopable color photosensitive material having photosensitive silver halide, a reducing agent, and a dye imparting material is a compound forming a dye having an absorption maximum at 400-700 nm and further incorporates a compound forming a dye having an absorption maximum at longer wavelengths than 725 nm expressed with formula I. In formula I, R1 and R2 are electron attractive groups of s p > 0.50 and X is atomic groups forming an aromatic cyclic which may have substituted groups and Z is H atom or a coupling type releasing group. Thus by using the photosensitive material, it becomes easy to read the information recorded with longer wavelength light than 750 nm.

Author(s): R. Matsushima
Title: Photochromic properties of 2-arylidene-1,3-bis(dicyanomethylene)indanes
Senryo to Yakuhin Vol. 37, No. 5, p. 116-123 (1992); ISSN: 0370-9671; CODEN: SETYAL

keywords: condensation of 1,3-bis(dicyanomethylene)indane with aromatic aldehydes
Abstract:
A series of 2-arylidene-1,3-bis(methylene) indane derivatives were prepared to investigate the relationship between the structure and photochromic properties. They underwent 6p-electrocyclic photoreactions to give colored forms in a similar manner to the photochromic fulgides, with much lower efficiencies both in solution and PMMA film. Thermal stabilities of the colored forms tended to decease in the order of thienyl > pyrrolyl > phenyl ring derivatives, while the efficiencies for photocoloration were in the reverse order. The photochromic performance of the system were generally poor as yet, though they featured coloration at near-IR region, resistance toward solvolytic degradations, and easy access of the materials, as compared to the photochromic fulgides.

Author(s): L.A. Chetkina, V.E. Zavodnik, A.N. Sobolev, V.K. Bel'skii, B. Bespalov and A.G. Abolin
Title: X-ray structural investigation of 1,3-Bis(dicyanomethylene)indane and its triethylammonium salt
Zh. Strukt. Khim. Vol. 32, No. 3, p. 49-54 (1991); ISSN: 0044-4634; CODEN: ZSTKAI
J. Struct. Chem. (USSR) (Engl. Transl.) Vol. 32, No. 3, p. 353-357 (1991); ISSN: 0022-4766; CODEN: JSTCAM

Abstract:
The title compound is monoclinic, space group P2₁/b, with a = 8.001(2) Å, b = 12.778(2) Å, c = 12.453(3) Å, and g 105.17(1) °; d_c = 1.309 for Z = 4. The salt of the title compound is monoclinic, space group I₂/a, with a = 14.438(3) Å, b = 23.915(5) Å, c = 11.344(2) Å, and g 102.20(2)°; d_c = 1.191 for Z = 8. The atom coordinates are given. The structures were solved by direct methods and refined by least-squares to R = 0.031 and 0.042, respectively. The bond lenghts and angels are described.

Author abstract:
Using x-ray structural analysis we have determined the molecular and crystal structure of 1,3-bis(dicyanomethylene)indane (space group P2₁/b, Z = 4, for 1148 reflections, R = 0.031) and its triethylammonium salt (space group I2/a, Z = 8, for 1448 reflections, R = 0.042). The rotation angles of the dicyanomethylene groups in relation to the planar indane fragment were insignificant (1.6 - 4.2°). Deprotonation leads to a considerable change in the geometry of the 5-membered ring of the indane part of the molecule and the C=C bond which joins it with strong delocalization along the chain of the C=C-C(H₂)-C=C bonds. In the neutral molecule we observed the participation of the CH₂ group of the 5-membered indane ring and the CH group of the 6-membered ring in intermolecular H bonds with nitrile N atoms. Cations and anions of the salt are linked by medium strength NH...N bonds (N...N 2.926 A).

Author(s): A.S. Batsanov, M.R. Bryce, S.R. Davies, J.A.K. Howard, R. Whitehead and B.K. Tanner
Title: Studies on p-acceptor molecules containing the dicyanomethylene group. X-ray crystal structure of the charge-transfer complex of tetramethyltetrathiafulvalene and 2,3-Dicyano-1,4-naphthoquinone: (TMTTF)₃-(DCNQ)₂
J. Chem. Soc., Perkin Trans. 2, p. 313-319 (1993); ISSN: 0300-9580; CODEN: JCPKBH

Author(s): C. Reidlinger, R. Dworczak, W.M.F. Fabian and H. Junek
Title: Structure-color correlations of Penta- and Heptamethines. Synthesis with Nitriles. XCIV.
Dyes Pigm. Vol. 24, No. 3, p. 185-204 (1994); ISSN: 0143-7208; CODEN: DYPIDX


Abstract:
The synthesis of asymmetric cyanine dyes (penta- and heptamethines), prepared by coupling Fischer's base with indandione, benzo[b]thiophene and pyrazole derivatives via a C-1 unit, is described. Three different synthetic strategies for substituted polymethines are presented. Dye characteristics are given and the correlation between the chemical structures and the dye properties are discussed by means of semi-empirical PPP calculations.

Author(s): J.M. Raimundo, P. Blanchard, I. Ledoux-Rak, R. Hierle, L. Michaux and J. Roncali
Title: Huge enhancement of the quadratic nonlinear optical susceptibility in push-pull chromophores based on bridged dithienylethylene spacers
Chem. Commun., No. 17, p. 1597-1598 (2000); ISSN: 1359-7345; CODEN: CHCOFS

Author(s): I. Ino, J.C. Zhong, M. Munakata, T. Kurod-Sowa, M. Maekawa, Y. Suenaga and Y. Kitamori
Title: 2-D- Interwoven and 3-D 5-fold interpenetrating silver(I) complexes 1-(Isocyanidomethyl)-1H-benzotriazole and 1,3-Bis(dicyanomethyidene)indane
Inorg. Chem. Vol. 39, No. 19, p. 4273-4279 (2000); ISSN: 0020-1669; CODEN: INOCAJ

Author(s): L. Valkunas, A. Gruodis, D. Juodzbalis and A. Urbas
Title: Nonlinear spectral effects in films and cystals of polar molecules
Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A Vol. 230, p. 163-168 (1993); ISSN: 1058-725X; CODEN: MCLCE9
Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A Vol. 228, p. 655-660 (1993); ISSN: 1058-725X;

Abstract:
The paper addresses the spectroscopic peculiarities of polar molecular crystals and films of dimethylaminebenzylidene-1,3-indandione (DMABI). Specific visible fluorescence bands for various modifications of the system are discovered. They are identical for all excitation conditions and seem to be correlated with the structural organization of the media. The infrared excitation of these bands is shown to be a two-step process which turns into the saturating regime at higher intensities.

Author(s): I.L. Belaits, N.I. Kunavin, R.V. Nurmukhametov and A.E. Podorol'skaya
Title: Absorption and luminescence spectra of 2-vinyl derivatives of 1,3-Indandione
Opt. Spektrosk. Vol. 38, No. 5, p. 908-912 (1975); ISSN: 0030-4034; CODEN: OPSPAM
Opt. Spectrosc. (USSR) (Engl. Transl.) Vol. 38, No. 5, p. 521-523 (1975); ISSN: 0030-400X; CODEN: OPSUA3

Abstract:
We have investigated the spectral luminescence properties (absorption spectra and phosphorescence spectra at 20 °C; luminescence spectra, quantum yield of fluorescence and phosphorescence, and phosphorescence lifetime at 77 K) of solutions of a series of vinyl-substituted 1,3-indandiones. We have determined the nature and the locations of the lower excited singlet and triplet levels of the pp* and np* type. On the basis of the relative positions of these levels, we have explained the spectral luminescence properties of these compounds, and we have observed in certain cases the activation of fluorescence in polar solvents. We have considered the energy of the np* state as a function of the molecular structure of the series of compounds investigated.

Author(s): N.S. Magomedova, Z.V. Zvonkova, M.G. Neigauz and L.A. Novakoskaya
Title: Crystal structure of the g-modification of 2-(p-dimethylaminobenzylidene)-1,3-indandione
Kristallografiya Vol. 25, No. 2, p. 400-402 (1980); ISSN: 0023-4761; CODEN: KRISAJ
Sov. Phys. Crystallogr. Vol. 25, No. 2, p. 230-232 (1980); ISSN: 0038-5638; CODEN: SPHCA6
keywords: X-ray structure of the g-modification of 2-(p-dimethylaminobenzylidene)-1,3-indandione
Abstract:
This communication gives the results of the g-modification of 2-p-dimethylaminobenzylidene-1,3-indandione (III), measured as a single crystal of 0.05 x 0.1 x 0.6 mm. The data for C₁₈H₁₅NO₂ are as follows: M = 277.18; a = 29.011(9) Å; b = 3.944(1) Å; c = 12.086(4) Å; V = 1383.1(7) ų; Z = 4; Fedorov group Pna2₁. The difference to other modifications of the molecule is discussed.

Author(s): N.S. Magomedova and Z.V. Zvonkova
Title: Crystal structure of the a-modification of 2-(p-dimethylaminobenzylidene)-1,3-indandione
Kristallografiya Vol. 23, No. 2, p. 281-288 (1978); ISSN: 0023-4761; CODEN: KRISAJ
Sov. Phys. Crystallogr. Vol. 23, No. 2, p. 155-159 (1978); ISSN: 0038-5638; CODEN: SPHCA6
keywords: X-ray structure of the a-modification of 2-(p-dimethylaminobenzylidene)-1,3-indandione
Abstract:
This communication gives the results of the a-modification of 2-p-dimethylaminobenzylidene-1,3-indandione, measured as a single crystal of 0.3 x 0.4 x 1.2 mm. The data for C₁₈H₁₅NO₂ are as follows: M = 277.18; a = 12.770(5) Å; b = 15.761(7) Å; c = 14.257(3) Å; b = 105.87(2) ° V = 2759 (4) ų; Z = 8; space group P2₁/c. Atomic coordinates, valence angles, bond length and planar fragments of the molecule are given.

Author(s): N.S. Magomedova, O.V. Kolninov, E.G. Rukhadze and Z.V. Zvonkova
Title: Photoelectric properties of crystalline modifications of 2-(p-dimethylaminobenzylidene)-indan-1,3-dione
Zh. Fiz. Khim. Vol. 49, No. 5, p. 1322-1323 (1975); ISSN: 0044-4537; CODEN: ZFKHA9
Russian J. Phys. Chem. Vol. 49, No. 5, p. 779-780 (1975); ISSN: 0036-0244; CODEN: RJPCAR
keywords: description of the three modifications of 2-(p-dimethylaminobenzylidene)-1,3-indandione
Abstract:
X-ray examination has been established three crystalline modifications, and the ratio of photocurrent to dark current has been measured.

Author(s): Y. Matsuda, K. Katou, H. Matsumoto, M. Yamashita, S. Ide, K. Takahashi, K. Torisu, K. Furuno and S. Maeda
Title: Synthesis of methine dyes having dimethylaminoindolizine skeleton as an electron donor
Yakugaku Zasshi Vol. 112, No. 1, p. 42-49 (1992); ISSN: 0031-6903 / 0372-7750; CODEN: YKKZAJ
J. Pharm. Soc. Jpn. Vol. 112, No. 1, p. 42-49 (1992);

Author(s): V. Petrow, J. Saper and B. Sturgeon
Title: New syntheses of heterocyclic compounds. Part X. 4-Azafluorenones
J. Chem. Soc., p. 2134-2139 (1949); ISSN: 0368-1769; CODEN: JCSOA9

Author(s): St. v. Konstanecki and L. Laczkowski
Title: Ueber Monooxybenzalindandione
Ber. dtsch. Chem. Ges. Vol. 30, p. 2138-2144 (1897); ISSN: 0365-9496; CODEN: BDCGAS

Author(s): A. Cornélis, S. Lambert, P. Laszlo and P. Schaus
Title: Analysis of Carbon-13 nuclear magnetic resonance shifts in terms of substituent parameters: statistical comparison of dual and single substituent parameter treatments
J. Org. Chem. Vol. 46, No. 10, p. 2130-2134 (1981); ISSN: 0022-3263; CODEN: JOCEAH


Abstract:
A systematic comparison is made, by using six different scales of substituent parameters, of the a-, b-, and g-carbon-13 chemical shifts for the olefinic moiety in four series of styrene derivatives. There is no systematic significant superiority, in general, of a dual substituent parameter (DSP) treatment with respect to the simpler single substituent parameter (MSP) treatment. In the case of the g-carbons, with the former type of analysis, the inductive effect is found to be more sensitive than the resonance effect to configurational differences.

Author(s): W.O. Teeters and R.L. Shriner
Title: A new preparation of Ninhydrin
J. Am. Chem. Soc. Vol. 55, p. 3026-3028 (1933); ISSN: 0002-7863; CODEN: JACSAT

keywords: Selendioxide-oxidation of 1,3-indandione; 1,3-indandione-2-carboxylic acid ethylester-sodium salt; condensation of phthalic acid diethylester with ethylacetate and sodium as base

Author(s): S. Ruhemann
Title: Triketohydrindene hydrate
J. Chem. Soc. Trans. Vol. 97, No. pt. 2, p. 2025-2031 (1910); ISSN: 0368-1645; CODEN: JCHTA3

keywords: 2,2-dichloro-1,3-indandione from ninhydrin and phosphorous pentachloride; chlorination of triketohydrindene

Author(s): S. Ruhemann
Title: Triketohydrindene Hydrate. Part III. Its relation to Alloxan
J. Chem. Soc. Trans. Vol. 99, p. 792-800 (1911); ISSN: 0368-1645; CODEN: JCHTA3

keywords: 1,3-indandione-2-carboxylic acid ethylester-sodium salt; condensation of phthalic acid diethylester with ethylacetate and sodium as base; condensation of 1,3-indandione with sodium-p-nitrodimethylaniline resulting in 2-(4-dimethylaminophenylimino)-indan-1,3-dione
2-(4-Dimethylaminophenylimino)-indan-1,3-dione mp. 211 °C, compare Roth, H.J.; Kok, W.: Arch. Pharmaz. 309, 1976, 92-98.

Author(s): H.J. Roth and W. Kok
Title: Zur Kenntnis der Ninhydrin-Reaktion, 4. Mitt. Reaktion mit 2- and 4-Dimethylaminoanilin
Arch. Pharm. Vol. 309, p. 92-98 (1976);

keywords: condensation of 1,3-indandione with p-nitrodimethylaniline resulting in 2-(4-dimethylaminophenylimino)-indan-1,3-dione
2-(4-Dimethylaminophenylimino)-indan-1,3-dione mp. 212 °C, compare Ruhemann, S.: J. Chem. Soc. 99, 1911, 792-800.

Author(s): W.H. Hunter and R.E. Jackmann
Title: The action of phosphorus pentachloride on 1,3-dioxoindane
J. Am. Chem. Soc. Vol. 55, p. 2567-2570 (1933); ISSN: 0002-7863; CODEN: JACSAT

keywords: action of PCl₅ on 1,3-indandione; 1,1-dichloroindan-3-one prepared from indan-1,3-dione and phosphorous pentachloride; chlorination of 1,3-indandione; 1,1,3,3-tetrachloroindane; 1,1,3-trichloro-2-indene

Author(s): W. Wislicenus
Title: Über die Einwirkung von Oxalester auf Lactone
Justus Liebigs Ann. Chem. Vol. 246, p. 342-347 (1888); ISSN: 0075-4617; CODEN: JLACBF

keywords: reaction of oxalic acid esters with phthalic acid anhydride

Author(s): W. Wislicenus
Title: Einwirkung von Essigester auf Phthalsäureester
Justus Liebigs Ann. Chem. Vol. 246, p. 347-355 (1888); ISSN: 0075-4617; CODEN: JLACBF

keywords: 1,3-Indandione-2-carboxylic acid ethylester-sodium salt; condensation of phthalic acid diethylester with ethylacetate and sodium as base; 2,2-Dibromo-1,3-indandione; Bromination of Indan-1,3-dione

Author(s): L. Flatow
Title: Über die Einwirkung von Brom and Chlor auf Natriumdiketohydrindencarbonsäureester
Ber. dtsch. Chem. Ges. Vol. 34, p. 2145-2149 (1901); ISSN: 0365-9496; CODEN: BDCGAS

keywords: 1,3-indandione-2-carboxylic acid ethylester-sodium salt; condensation of phthalic acid diethylester with ethylacetate and sodium as base; 2,2-dibromo-1,3-indandione; bromination of indan-1,3-dione; 2,2-dichloro-1,3-indandione; chlorination of indan-1,3-dione

Author(s): W.H. Hunter and E.C. Yackel
Title: Some derivatives of 1,3-Diketohydrindene
J. Am. Chem. Soc. Vol. 58, p. 1395-1396 (1936); ISSN: 0002-7863; CODEN: JACSAT

keywords: 2,2-dibromo-1,3-indandione; bromination of indan-1,2,3-trione; ninhydrin

Author(s): W. Wislicenus and F. Melms
Title: Ringschlußsynthesen mit Oxalester
Justus Liebigs Ann. Chem. Vol. 436, p. 101-112 (1924); ISSN: 0075-4617; CODEN: JLACBF

keywords: condensation of benzylmethylketone and oxalic acid esters resulting in 1-phenylcyclopentan-2,4,5-trione; 3-phenylcyclopentan-1,2,4-trione; 2-phenylcyclopentan-1,3,5-trione; blue coloration of a solution of 3-phenylcyclopentan-1,2,4-trion on treatment with sodium hydroxide; occurence of blue colouration on alkali hydroxide treatment of a solution of 3-phenylcyclopentan-1,2,4-trione

Author(s): G.M. Robinson
Title: A reaction of Homopiperonyl and of Homoveratryl alcohols
J. Chem. Soc. Trans. Vol. 107, No. pt. 1, p. 267-276 (1915); ISSN: 0368-1645; CODEN: JCHTA3

keywords: 3,3',4,4'-tetramethoxybenzophenone

Author(s): W.H., jr. Perkin and C. Weizmann
Title: Some derivatives of Catechol, Pyrogallol, Benzophenone, and of substances allied to the natural coloring matters
J. Chem. Soc. Trans. Vol. 89, No. pt. 2, p. 1649-1665 (1906); ISSN: 0368-1645; CODEN: JCHTA3

keywords: 3,3',4,4'-tetramethoxybenzophenone

Author(s): W. Lawson and W.H., jr., Robinson, R. Perkin
Title: Harmine and Harmaline. Part VII. A Synthesis of apoHarmine and of certain Carboline and Copyrine derivatives
J. Chem. Soc. Trans. Vol. 125, No. pt. 1, p. 626-657 (1924); ISSN: 0368-1645; CODEN: JCHTA3

keywords: 3,3',4,4'-tetramethoxybenzophenone

Author(s): H. Nishikawa and W.H., jr., Robinson, R. Perkin
Title: Harmine and Harmaline. Part VIII. The constitution of certain Harmaline derivatives
J. Chem. Soc. Trans. Vol. 125, No. pt. 1, p. 657-663 (1924); ISSN: 0368-1645; CODEN: JCHTA3

Author(s): H. Meyer
Title: Über eine allgemein anwendbare Methode zur Darstellung von Chloriden der organischen Säuren
Monatsh. Chem. Vol. 22, p. 415-442 (1901); ISSN: 0026-9247; CODEN: MOCMB7

keywords: 3,4-dimethoxybenzoyl chloride from treatment of 3,4-dimethoxybenzoic acid and thionyl chloride at ambient temperature

Author(s): S. v. Konstanecki and J. Tambor
Title: Synthese des Maclurin-pentamethylethers
Ber. dtsch. Chem. Ges. Vol. 39, p. 4022-4027 (1906); ISSN: 0365-9496; CODEN: BDCGAS

keywords: 3,3',4,4'-tetramethoxybenzophenone

Author(s): J.L. Hartwell and S.R.L. Kornberg
Title: Some a,b-Diphenylethylamines
J. Am. Chem. Soc. Vol. 67, p. 1606-1608 (1945); ISSN: 0002-7863; CODEN: JACSAT

keywords: 3,3',4,4'-tetramethoxybenzophenone

Author(s): W. v. E. Doering and J.A. Berson
Title: A Re-examination of the Diisohomogenol structure
J. Am. Chem. Soc. Vol. 72, p. 1118-1123 (1950); ISSN: 0002-7863; CODEN: JACSAT

keywords: 3,3',4,4'-tetramethoxybenzophenone

Author(s): W. Wislicenus and A. Kötzle
Title: Über Derivate des Diketohydrindens
Justus Liebigs Ann. Chem. Vol. 252, p. 72-79 (1889); ISSN: 0075-4617; CODEN: JLACBF

keywords: bindone; monobromo bindone; 1,3-indandione-2-carboxylic acid; condensation of 1,3-indandione with benzaldehyde forming 2-benzylidene-1,3-indandione; formation of bindone

Author(s): W. Wislicenus and A. Kötzle
Title: Über die Einwirkung von Propionsäureester auf Phthalsäureester (Synthesen von Hydrindenderivaten)
Justus Liebigs Ann. Chem. Vol. 252, p. 80-87 (1889); ISSN: 0075-4617; CODEN: JLACBF

Author(s): W. Wislicenus
Title: Über die Vereinigung verschiedener Ester durch Natrium
Ber. dtsch. Chem. Ges. Vol. 20, p. 589-595 (1887); ISSN: 0365-9496; CODEN: BDCGAS

keywords: 1,3-indandione-2-carboxylic acid ester-sodium salt; condensation of phthalic acid diethylester with ethylacetate and sodium as base

Author(s): S. Gabriel
Title: rearrangement of phthalylidene-derivatives forming derivatives of a,g-Diketohydrindene
Ber. dtsch. Chem. Ges. Vol. 26, p. 951-955 (1893); ISSN: 0365-9496; CODEN: BDCGAS

keywords: 1,3-indandion-2-carboxylic acid ethyl ester-sodium salt; Umlagerung des Kondensationsproduktes aus Phthalsäurediethylester and Ethylacetat mit Natriummethanolat

Author(s): H. Gruen and B.E. Norcross
Title: A modification and extension of an elementary preparation of ninhydrin
J. Chem. Educ. Vol. 42, p. 268 (1965); ISSN: 0021-9584; CODEN: JCEDA8

keywords: 1,3-indandione; condensation of indan-1,3-dione forming bindone on treatment with diluted hydrochloric acid; 1,3-indandione-2-carboxylic acid ethylester-sodium salt; rearrangement of condensation products from phthalic acid dimethylester and ethylacetate on treatment with sodium methoxide

Author(s): A. Schwarz, G. Uray and H. Junek
Title: Notiz über die Reaktion von Carbonsäurehalogeniden mit Ninhydrin
Liebigs Ann. Chem., p. 1919-1922 (1980); ISSN: 0170-2041; CODEN: LACHDL

keywords: 2,2-dichloro-1,3-indandione; chlorination of indan-1,2,3-trione; reaction of ninhydrin with thionyl chloride

Author(s): H. Junek
Title: Synthesen mit Nitrilen. 8. Mitt.; Ringschlüsse zu 1,2-Dihydropyridinen
Monatsh. Chem. Vol. 95, p. 1201-1206 (1964); ISSN: 0026-9247; CODEN: MOCMB7

keywords: 1,3-indandione; malonodinitrile; 1-(dicyanmethylene)-indan-3-one; monosubstitution product of indan-1,3-dione with malononitrile

Author(s): H. Staudinger
Title: Oxalylchlorid. 3. Mitteilung. Einwirkung von Oxalylchlorid auf Carbonylhaltige Verbindungen
Ber. dtsch. Chem. Ges. Vol. 42, p. 3966-3985 (1909); ISSN: 0365-9496; CODEN: BDCGAS

keywords: chlorination of ketones; geminal dichlorides from carbonyl compounds

Author(s): P.K. Grover, G.D. Shah and R.C. Shah
Title: Xanthones. Part IV. A new synthesis of hydroxyxanthones and Hydroxybenzophenones
J. Chem. Soc., p. 3982-3985 (1955); ISSN: 0368-1769; CODEN: JCSOA9

keywords: 2,2'-dihydroxy-4,4'-dimethoxybenzophenone; 3,6-dimethoxyxanthone; reaction of 2,2'-dihydroxy-4,4'-dimethoxybenzophenone at 180-200 °C in water using an autoclave; water separation

Author(s): E.Y. Gudriniece, P.V. Pastors and Y.V. Priede
Title: The synthesis of 2-cyanoindan-1,3-dione
J. Org. Chem. USSR Vol. 9, No. 6, p. 1337 (1973); ISSN: 0022-3271; CODEN: JOCYA9
Zh. Org. Khim. Vol. 9, No. 6, p. 1307-1308 (1973); ISSN: 0514-7492; CODEN: ZORKAE
keywords: condensation of phthalic acid anhydride with cyanoacetic acid ethylester forming cyanomethylphthalide; rearrangement of cyanomethylphthalide formimg 2-cyano-1,3-indandione on treatment with sodium methoxide

Author(s): N.S. Zefirov and D.I. Makhon'kov
Title: Reaction of Triphenylphosphine with Tetracyanomethane
J. Org. Chem. USSR Vol. 9, No. 4, p. 879 (1973); ISSN: 0022-3271; CODEN: JOCYA9
Zh. Org. Khim. Vol. 9, No. 4, p. 851 (1973); ISSN: 0514-7492; CODEN: ZORKAE
keywords: reaction of triphenylphosphine with tetracyanomethane; dicyanomethylenephosphorane; pseudo-halogenic character of tetracyanomethane

Author(s): B.M. Gladshtein, V.M. Zimin, I.M. Shishkov and I.A. Revel'skii
Title: Rearrangement of derivatives of phosphorus(III) acids under the action of protonating reagents with the formation of a C-P bond
J. Gen. Chem. USSR Vol. 57, No. 10, p. 2051-2056 (1987); ISSN: 0022-1279; CODEN: JGCHA4
Zh. Obshch. Khim. Vol. 57, No. 10, p. 2294-2300 (1987); ISSN: 0044-460X; CODEN: ZOKHA4
keywords: reaction of triethylphosphite with malodinitrile; dicyanomethylene phosphonic acid diethylester; trialkylphosphites; malonodinitrile; malonic acid dinitrile; diethyl (dicyanomethyl)phosphonate; reaction of trialkylphosphites with benzylcyanide

Author(s): T.G. Rymareva, B.A. Khaskin, V.B. Sanddakov and V.K. Promonenkov
Title: Diethyl chlorphosphite reaction with Malonodinitril
J. Gen. Chem. USSR Vol. 51, No. 11, p. 2271 (1981); ISSN: 0022-1279; CODEN: JGCHA4
Zh. Obshch. Khim. Vol. 51, No. 11, p. 2633-2634 (1981); ISSN: 0044-460X; CODEN: ZOKHA4
keywords: reaction of diethylchlorophosphite with malodinitrile; dicyanomethylene-O,O-diethylphosphorane; malonodinitrile; malonic acid dinitrile

Author(s): P.A. Chopard, R.F. Hudson and G. Klopman
Title: Nucleophilic reactivity. Part VI. The reaction between Triphenylphosphine and a-halogenated ketones
J. Chem. Soc., p. 1379-1386 (1965); ISSN: 0368-1769; CODEN: JCSOA9

keywords: reaction of triphenylphosphane with a-Halogenoketones; triphenylphosphine