Author(s): D.R. Gedge und G. Pattenden
Title: Rearrangement of 4-ylidenebutenolides to cyclopentene-1,3-diones: synthesis of Calythrone and related compounds
J. Chem. Soc., Chem. Commun., p. 880-882 (1978); ISSN: 0022-4936; CODEN: JCCCAT

keywords: 2,3-Dimethyl-1,4-cyclopent-2-endione; 4,5-Dimethyl-1,3-cyclopent-4-endione

Author(s): T.K. Clausen, S. Scheibye und S.-O. Iawesson
Title: Thiation with 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphophetane 2,4-disulfide: N-Methylthiopyrrolidone
Org. Synth. Vol. 62, p. 158-161 (1984);

keywords: Lawesson-Reagenz; Thiocarbonylverbindungen aus Carbonylverbindungen

Author(s): M.W. Lee und W.C. Herndon
Title: Stereochemistry of the Furan-Maleic anhydride cycloaddition
J. Org. Chem. Vol. 43, No. 3, p. 518 (1978); ISSN: 0022-3263; CODEN: JOCEAH

keywords: Cycloaddition von Furan an Maleinsäureanhydrid; Schutzgruppe für die Doppelbindung der Maleinsäure; Diels-Alder-Rektion

Author(s): J.-S. Lee und S.C. Nyburg
Title: Refinement of the a-modification of 9,9'-Bifluorenylidene, C₂₆H₁₆, and structure analyses of the b-modification, the 2:1 pyrene complex, 2(C₂₆H₁₆)*C₁₆H₁₀, and the 2:1 Perylene complex, 2(C₂₆H₁₆)*C₂₀H₁₂
Acta Crystallogr. Sect. C: Cryst. Struct. Commun. Vol. C41, p. 560-567 (1985); ISSN: 0108-2701; CODEN: ACSCEE

Author(s): J.E. Banfield, G.D. Fallon und B.M. Gatehouse
Title: Heterocyclic derivatives of guanidine. VI. Formation and X-ray structure determination of 2-dimethylamino-7,8-diphenyl-4,6-dihydropyrrolo[1,2-a]pyrimidine-4,6-dione
Aust. J. Chem. Vol. 40, p. 1003-1009 (1987); ISSN: 0004-9425; CODEN: AJCHAS

keywords: Reaktion von (E)-2,3-diphenyl-but-2-enedinitrile mit Guanidinen; Hydrolyse zu 2,3-Diphenylmaleinsäureanhydrid; 2,3-Diphenyl-2-buten-1,4-dicarbonsäurenitril; 2,3-Diphenylbut-2-en-1,4-dinitril; 2,3-Diphenylmaleinsäure; 2,3-Diphenylmaleinsäureanhydrid

Inventor(s): K. Sato, K. Watanabe und 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: Iminoindanylidene derivates of 1,3-Bis(dicycanomethylene)indane
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.

Author(s): F.A. Gollmick und H. Berg
Title: Sensitized photo-oxidation by methylene blue, thiopyronine and pyronine. I. Flash-photo-oxidation of p-diaminotoluene
Photochem. Photobiol. Vol. 7, No. 5, p. 471-475 (1968); ISSN: 0031-8655; CODEN: PHCBAP

Inventor(s): Y. Matsushima, A. Tomota, A. Kaneko, M. Ishizuka und 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


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): T. Hioki und A. Tomioka
Title: Methine compound, its production and optical information recording medium made thereof
(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


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 600-800nm and exhibits high reflectance in a region of 600-870nm 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.

Author(s): B.P. Bespalov, A.G. Abolin, V.K. Bel'skii, V.E. Zavodnik, A.N. Sobolev und L.A. Chetkina
Title: Reaction of Dicyanomethylene compounds with Nitrosoaryls
J. Org. Chem. USSR Vol. 27, No. 4, p. 720-727 (1991); ISSN: 0022-3271; CODEN: JOCYA9
Zh. Org. Khim. Vol. 27, No. 4, p. 836-845 (1991); ISSN: 0514-7492; CODEN: ZORKAE

Abstract:
With nitrosoaryls tetracyanoethylene, tetracyanoquinodimethane, and 2-dicyanomethyleneindane-1,3-dione gives small yields of the corresponding dicyanomethylene anils. With 1-dicyanomethyleneindan-3-one and 1,3-bis(dicyanomethylene)indane in polar solvents the nitrosoaryls form anils at position 2 of the indane. In nonpolar solvents 1,3-bis(dicyanomethylene)indan-2-one is formed preferentially from 1,3-bis(dicyanomethylene)indane. In nonpolar solvents at 100 °C the anils of 1,3-bis(dicyanomethylene)indane are converted into derivatives of indenoquinoline, while in polar solvents in the presence of bases derivatives of indenopyrrole are formed.

Author(s): A.M. Asiri
Title: Synthesis and characterization of dyes exemplified by 2-arylidene-1-dicyanomethyleneindanes
Dyes Pigm. Vol. 42, No. 3, p. 209-213 (1999); ISSN: 0143-7208; CODEN: DYPIDX

keywords: methine dyes; dicyanomethylene; dicyanomethyleneindane; chalcones; Knoevenagel condensation; arylidene dicyanomethylene indanes
Abstract:
The synthesis of methine dyes formed by Knoevenagel condensation of aromatic aldehydes with 1-dicyanomethylene indane 2 afforded a novel series of dyes absorbing in the region 490-593 nm. Substituents on the aromatic aldehyde moiety have a significant effect on the visible absorption maxima of the dyes; increasing the solvent polarity also had a pronounced effect on the absorption maxima.

Author(s): Lidia S. Konstantinova, Oleg A. Rakitin, Charles W. Rees, Ljudmila I. Souvorova und Tomas Torroba
Title: One-pot synthesis of indeno-1,2-thiazines, -(1,2)dithioles and thiophenes; new liquid crystalline materials
J. Chem. Soc., Perkin Trans. 1, No. 8, p. 1023-1028 (1999); ISSN: 0300-922X; CODEN: JCPRB4


Abstract:
In a search for further examples of a new type of discotic liquid crystal, we have examined the reactions of S₂Cl₂ in the presence of a chlorinating agent (NCS) and a base (Huenig's base or DABCO), mostly in THF, with cyclopent-1-enylacetic acid 6, inden-3-ylacetic acid 8 and its nitrile 16 and 1-(dicyanomethylene)indane 22. The cyclopentene acid 6 gives purple crystals of the trichlorocyclopenta(1,2)dithiole ester 7, the product of heterocyclic ring formation, chlorination and dehydrochlorination and, unexpectedly, conversion of the acid in THF into its 4-chlorobutyl ester. Indenylacetic acid 8 gives methyleneindenes 10 and 11, the tricyclic 1,2-dithiolone 12 and the deep purple thiophene 13. Indenylacetonitrile 16 gives the chlorocyanomethylene indane 17 and the E- and Z-isomers of both the dichloroindene 18 and the monochloroindane 19, depending upon the precise reaction conditions. Dicyanomethylene indane 22 gives the dichloroindene 23 and the red, thermochromic indeno-1,2-thiazine 24; the analogous cyano-ester 25 gives the corresponding products. On melting, crystals of 13 and 23 are strongly birefringent. Mechanisms are proposed for the new transformations.

Author(s): Lidia S. Konstantinova, Oleg A. Rakitin, Charles W. Rees, Ljudmila I. Souvorova, Tomas Torroba et al.
Title: One-pot synthesis of new liquid crystalline indeno heterocyclic materials
Chem. Commun., No. 1, p. 73-74 (1999); ISSN: 1359-7345; CODEN: CHCOFS


Abstract:
Disulfur dichloride converts 1-(dicyanomethylene)indane 3 into the methyleneindene 4 and the red indeno-1,2-thiazine 5; it also converts inden-3-ylacetic acid 7 into methyleneindenes 8 and 9, dithiolone 10 and the deep purple thiophenone 11; upon melting crystals of 4 and 11 are strongly birefringent and 5 exhibits thermochromicity; mechanisms are outlined for the novel transformations and X-ray crystal structures for 5 and 10 are analysed.

Author(s): P.M. Borsenberger, E.H. Magin und J. Shi
Title: Charge transport in vapor deposited molecular glasses
Physica B: Condensed Matter Vol. 217, No. 3-4, p. 212-220 (1996); ISSN: 0921-4526; CODEN: PHYBE3


Abstract:
Hole mobilities have been measured in a series of vapor deposited molecular glasses over a wide range of fields and temperatures. The results are described by a theory based on disorder, due to Bässler and coworkers. The theory is based on the assumption that charge transport occurs by hopping through a manifold of localized states with superimposed energetic and positional disorder. A key parameter of the theory is, the energy width of the hopping site manifold. Values of are in agreement with a model based on dipolar disorder, due to Young. The model assumes that the total width is comprised of a dipolar component and a van der Waals component. These results, in conjunction with literature results for a wide range of donor and acceptor glasses, suggest that the van der Waals component is largely of positional or geometrical origin.

Author(s): L. Sicot, C. Fiorini, A. Lorin, J.-M. Nunzi, P. Raimond und C. Sentein
Title: Dye sensitized polythiophene solar cells
Synth. Metals Vol. 102, No. 1-3, p. 991-992 (1999); ISSN: 0379-6779; CODEN: SYMEDZ

keywords: solar cells; spin-cast semiconducting films; polythiophene and derivatives
Abstract:
The photovoltaic characteristics of spin-coated thin films of polythiophene sensitized with two diffrent dyes have been measured. We reported on the influence of the affinity between the polymer and the dye. By changing the dye, the power conversion efficiency is multiplied by 20 to reach 0.01% under a white light of 50 mW.cm-2.

Author(s): L. Sicot, C. Fiorini, A. Lorin, P. Raimond, C. Sentein und J.-M. Nunzi
Title: Improvement of the photovoltaic properties of polythiophene-based cells
Solar Energy Materials and Solar Cells Vol. 63, No. 1, p. 49-60 (2000); ISSN: 0927-0248; CODEN: SEMCEQ

keywords: organic semiconductor; polymer; spectral sensitization; molecular diode; photovoltaic cell
Abstract:
The photovoltaic properties of organic cells based on a polythiophene film have been studied. An external power efficiency of 10-4 % has been obtained in the pristine polymer diode. In order to improve this result, three complementary routes have been investigated. Optical sensitization of the polythiophene with a dye of the indane group leads to a 75 increase in power efficiency. A hybrid molecular/polymeric p-n type junction instead of the original Schottky type provides a 0.15% efficiency. Molecular rectification in oriented polymers incorporating diode-like chromophores increases the PV efficiency by a factor of 40.

Author(s): R. Gompper
Title: Novel donor-acceptor substituted heteroaromatic compounds
Bull. Soc. Chim. Belg. Vol. 92, No. 9, p. 781-792 (1983); ISSN: 0037-9646 / 0374-6585; CODEN: BSCBAG


Abstract:
Vinamidinium salt can be converted via 1,5-dipolar cyclization into electron-rich thiophenes, pyrroles, thiazoles and imidazoles. Diazaquinoneiminium salts react with nucleophiles to methylenepiperazines and dihydropyrazines. Donor-substituted 1,3,5,7-tetrazocines, cyclopentadienylium and aza(diaza)cyclopentadienylium salts, though formally antiaromatic, are stable compounds.

Author(s): Volker Figala, Thomas Gessner, Rudolf Gompper, Erich Haedicke und Stefan Lensky
Title: 1,4-Dibromo-2,5-bis-dicyanomethylene-1-(1-pyridinio)-3-cyclopentene-1-ides: Novel Pyridinium Ylides of the Cyclopentadiene Series
Tetrahedron Lett. Vol. 34, No. 40, p. 6375-6378 (1993); ISSN: 0040-4039; CODEN: TELEAY

keywords: ylides; tetracyanoethylene; cycloaddition; betaine dyes
Abstract:
Pyridiniotetrabromocyclopentadienides react with tetracyanoethylene to form the title ylides in which the pyridinium ring and the cyclopentenide moiety are orthogonally arranged.

Author(s): S. Ruhemann
Title: Triketohydrindene Hydrate. Part IV. Hydrindantin and its analogues
J. Chem. Soc. Trans. Vol. 99, p. 1306-1310 (1911); ISSN: 0368-1645; CODEN: JCHTA3

Author(s): H.-J. Timpe und K.-P. Kronfeld
Title: Light-induced polymer and polymerization reactions XXXIII. Direct photoinitiation of methyl methacrylate polymerization by excited states of ketones
J. Photochem. Photobiol., A: Chem. Vol. 46, p. 253-267 (1989); ISSN: 1010-6030; CODEN: JPPCEJ

keywords: BTX; thiopyronine; thioxanthone; 3,6-bis(dimethylamino)-thioxanthone (BTX); 3,6-bis(dimethylamino)-thioxanthylium-chloride; 3,6-bis(dimethylamino)-thioxanthone; 9-acridinone; thioxanthone; xanthone; N-methylacridone; 10-methylacridone
Abstract:
The S₁ and T₁ excited states of several aromatic ketones (benzophenone, xanthone, fluorenone, thioxanthone, acridone, N-methylacridone) are quenched by methyl methacrylate (MMA). The rate constants of T₁ quenching (k³_q) measured by means of flash experiments show a linear log k³q vs. ET relationship. Results of kinetic treatment agree with the formation of 1,4-diradicals which decompose mainly into the starting materials, whilst some initiate the polymerization of MMA. Data of the kinetic experiments of polymer formation (monomer exponents, light intensity exponents) accord with such a mechanism. The polymers obtained contain the corresponding ketone moiety, identified by absorption and fluorescence measurements.

Author(s): J. Suszko und S. Kinastowski
Title: O Strukture czasteczowwej i wla'sciwo'sciach estru ftalilo- oraz estru ftalidylomalonowego
Roczniki Chemii (Ann. Soc. Chim. Polonorum) Vol. 41, p. 111-117 (1967); ISSN: 0035-7677; CODEN: ROCHAC

keywords: Umsetzung von Phthalylchlorid mit Malonsäurestern

Author(s): J.E. Banfield
Title: Heterocyclic derivatives of Guanidine. Part I. 2H-Pyrroles and 1H-Isoindoles
J. Chem. Soc., p. 2108-2119 (1960); ISSN: 0368-1769; CODEN: JCSOA9

keywords: 2,3-Diphenylmaleinic acid imide; 2,3-Diphenyl-2-butene-1,4-dicarboxylic acid nitrile; 2,3-Diphenylbut-2-ene-1,4-dinitrile; 2,3-Diphenylmaleinic acid; 2,3-Diphenylmaleinic acid anhydride

Author(s): A.T. Blomquist und E.A. LaLancette
Title: Diphenylcyclobutadienoquinone. Synthesis and structure
J. Am. Chem. Soc. Vol. 83, p. 1387-1391 (1961); ISSN: 0002-7863; CODEN: JACSAT

keywords: 2,3-Diphenylbernsteinsäuredichlorid

Author(s): H. Hashimoto, T. Nakashima, K. Hattori, T. Yamada, T. Mizoguchi, Y. Koyama und T. Kobayashi
Title: Structure and non-linear optical properties of polar carotenoid analogues
Pure & Appl. Chem. Vol. 71, No. 12, p. 2225-2236 (1999); ISSN: 0033-4545; CODEN: PACHAS

keywords: 1,3-bis(dicyanomethylene)indane; carotenoides; 1,3-indandione; retinal
Abstract:
The structures and non-linear optical properties of polar carotenoid analogues, in which electron-accepting groups were introduced to the polyene backbone of carotenoids, were studied. Molecular and crystal structures of a novel polar carotenoid analogue b-ionylidene-2,4-dinitrophenylhydrazone, that is applicable as a second-order non-linear optical material, are introduced. Stark spectroscopy, in order to determine the non-linear polarizabilities, is demonstrated. Non-linear polarizabilities of indan-1,3-dione and its mono- and bis-dicyano-methylene derivatives of retinal, that are applicable as third-order non-linear optical materials, are introduced.

Author(s): E.G. Marsden und S. Smiles
Title: The synthesis of derivatives of thioxanthone from aromatic disulfides
J. Chem. Soc. Trans. Vol. 99, p. 1353-1358 (1911); ISSN: 0368-1645; CODEN: JCHTA3

keywords: synthesis of thioxanthones from sulfinic acids; 1,4-dimethylthioxanthone; condensation of 4-dimethylaminosulfinic acid with 3-hydroxybenzoic acid; 1,3-dimethylthioxanthone; bromothioxanthone; chloroethoxythioxanthone; 1-chloro-4-hydroxythioxanthone or 1-hydroxy-4-chlorothioxanthone

Author(s): H.T. Clarke und S. Smiles
Title: The synthesis of derivatives of thioxanthone. Part III. 1,4-Dihydroxythioxanthone
J. Chem. Soc. Trans. Vol. 99, p. 1535-1539 (1911); ISSN: 0368-1645; CODEN: JCHTA3

keywords: 1,4-Dihydroxythioxanthone; 1,4-Dimethoxythioxanthone

Author(s): H. Christopher und S. Smiles
Title: The synthesis of derivatives of thioxanthone. Part VI. Synthesis from aromatic sulphinic acids
J. Chem. Soc. Trans. Vol. 99, p. 2046-2051 (1911); ISSN: 0368-1645; CODEN: JCHTA3

keywords: 2-Hydroxythioxanthone; 2-Hydroxy-7-methylthioxanthone; 4-Hydroxy-7-methylthioxanthone; 2-Aminothioxanthone; 4-Aminothioxanthone; 2-Amino-7-methylthioxanthone; 2-Hydroxy-5-methylthioxanthone

Author(s): W.G. Prescott und S. Smiles
Title: The interaction of aromatic disulfides and sulphuric acid
J. Chem. Soc. Trans. Vol. 99, p. 640-649 (1911); ISSN: 0368-1645; CODEN: JCHTA3

Author(s): H. Decker und G. Dunant
Title: Zur Reduktion der Cylaminone II. Über Bi-acridyl
Ber. dtsch. Chem. Ges. Vol. 42, p. 1176-1178 (1909); ISSN: 0365-9496; CODEN: BDCGAS

Author(s): H. Decker und G. Dunant
Title: Über das Vorkommen des Hydroacridins im Steinkohlenteer
Ber. dtsch. Chem. Ges. Vol. 42, p. 1178-1179 (1909); ISSN: 0365-9496; CODEN: BDCGAS

Author(s): S. Juršenas, V. Gulbinas, Z. Kuprionis, R. Kananavicius, G. Kodis, T. Gustavsson, J.-C. Mialocq und L. Valkunas
Title: Femtosecond excited-state dynamics in N,N-dimethylaminobezylidene-1,3-indandione (DMABI) films
Synth. Metals Vol. 109, No. 1-3, p. 169-172 (2000); ISSN: 0379-6779; CODEN: SYMEDZ

keywords: organic molecular crystals; excitons; self-trapping; femtosecond spectroscopy; luminescence; annihilation
Abstract:
Ultrafast exciton dynamics in polycrystalline films of dipolar N,N-dimethylaminobenzylidene-1,3-indandione (DMABI) molecules was studied by femtosecond luminescence upconversion and transient absorption techniques. An enhanced nonradiative relaxation of the excitons, taking place on the subpicosecond time scale, was observed. It was attributed to the initial localisation and thermalisation of the self-trapped excitons. One-dimensional exciton–exciton annihilation was observed under high excitation conditions.

Author(s): V. Gulbinas, G. Kodis, S. Juršenas, L. Valkunas, A. Gruodis, J.-C. Mialocq, S. Pommeret und T. Gustavsson
Title: Charge transfer induced twisting of N,N-dimethylaminobenzylidene-1,3-indandione in solution
J. Phys. Chem. A Vol. 103, No. 20, p. 3969-3980 (1999); ISSN: 1089-5639; CODEN: JPCAFH


Abstract:
Nonradiative excited-state relaxation via charge transfer induced twisting of N,N dimethylaminobenzylidene-1,3-indandione (DMABI) in solution was investigated by means of picosecond transient absorption and femtosecond fluorescence spectroscopy. The analysis of the experimental data allows us to distinguish between different reaction stages of the molecular twisting in excited and ground states, as well as to consider the molecular dynamics along reactive (twisting) and nonreactive (solvation) coordinates. Quantum chemical calculations of the electronic structure of DMABI and its dependence on the molecular conformation are disc ussed in order to identify the bonds) involved in the twisting reaction. It is found that such a twisting bond is the C=C double bond, which is substantially weakened in the excited state.

Author(s): S. Juršenas, V. Gulbinas, T. Gustavsson, J.-C. Mialocq und L. Valkunas
Title: Femtosecond fluorescence spectroscopy of self-trapped charge-transfer excitons in films of dimethylaminobenzylidene 1,3-indandione (DMABI)
Liet. Fiz. Zh. Vol. 38, No. 1, p. 53-57 (1998); ISSN: 1392-1932; CODEN: LFZUE7
Lith. J. Phys. Vol. 38, No. 1, p. 53-57 (1998);

Abstract:
Ultrafast relaxation processes in 2-[4-(dimethylamino)benzylidene]-1,3-indandione molecular films are studied by fs luminescence spectroscopy. Vibronic relaxation and formation of self-trapped exciton states in a polar molecular film occur extremely fast, in the time scale below 100 fs. Complex dynamics of the redistribution of excitation energy from shallow to deeply trapped exciton states separated by an activation barrier are observed. The equilibration between 2 self-trapped exciton states is established within 20 ps after excitation.

Author(s): L. Valkunas, D. Juodzbalis, A. Urbas, A. Gruodis, A.A. A. Durandin, E. Silinsh, A. Klimkans und S. Larsson
Title: Visible fluorescence on the IR excitation of polar dimethylaminobenzylidende 1,3-indandione crystals
Adv. Mater. Opt. Electron. Vol. 2, No. 5, p. 221-232 (1993); ISSN: 1057-9257; CODEN: AMELE7


Abstract:
A novel nonlinear fluorescence (NLF) effect in polar dimethylaminobenzylidene 1,3-indandione (DMABI) crystals is presented and discussed. A single crystal or vacuum-evaporated layer of MABI excited in the IR region at 1064 nm (by a Q-switched YAG laser) emits red light in the visible region of the spectrum at 600-740 nm depending on the DMABI crystal modification. This anti-Stokes luminescence shows a quadratic dependence on the exciting light intensity which transforms to a linear dependence at very high excitation intensities. The observed NLF effect under IR excitation is detected by optical transitions into intermol. charge transfer (CT) states. Probably the photoexcited singlet 1CT excitations may either interact in a quadratic single-singlet (1CT + 1CT) annihilation reaction or, more probably, form long-lived triplet 3CT excitons via a hyperfine interaction effect which may subsequently annihilate in a similar bimolecular fusion reaction (3CT + 3CT). In both cases the excited mol. singlet state S1 is formed and thus the NLF effect is due to singlet-singlet or triplet-triplet fusion of CT excitons. A detailed energy diagram and kinetic description of the model are presented. Quantum chemical calculations of the electronic structure of the DMABI mol. illustrate the dipolar nature of its ground and excited states.

Author(s): V. Gulbinas, G. Kodis und L. Valkunas
Title: Visible luminescence of dimethylaminobenzylidene-1,3-indandione compounds excited by ultrashort infrared light pulses
J. Phys. Chem. Vol. 100, No. 50, p. 19441-19445 (1996); ISSN: 0022-3654; CODEN: JPCHAX


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

Author(s): Juršenas, S., V. V. Gulbinas, T. Gustavsson, S. Pommeret, J. -C. Mialocqc und L. Valkunas
Title: Excitation relaxation in films of dipolar N,N-dimethylaminobenzylidene 1,3-indandione molecules
Chem. Phys. Vol. 275, No. 1-3, p. 231-242 (2002); ISSN: 0301-0104; CODEN: CMPHC2


Abstract:
Ultrafast relaxation of self-trapped (ST) excitons in polycrystalline film of N,N-dimethylaminobenzylidene-1,3-indandione (DMABI) molecules, which possess pronounced donor–acceptor properties, is studied by using femtosecond luminescence up-conversion spectroscopy. Exciton relaxation dynamics is compared to excitation decay obtained for DMABI molecules embedded in a rigid transparent matrix. Excitons in the film undergo rapid self-trapping on the time scale below 100 fs. A strong nonradiative recombination of ST excitons is observed on the subpicosecond time scale, which is shown to occur concurrently with their final localization. This final localization is attributed to the cooling of locally heated (up to 600 K) ST excitons, that occurs with the time constant c=800 fs. The fast nonradiative relaxation is assigned to the thermally activated transition of the hot excitons to the ground state during their thermalization. After the fast relaxation stage is completed, the second, slow exciton relaxation stage emerges, which is attributed to one-dimensional migration of excitons and their nonradiative decay on structural defects.

Author(s): H. Schwartz, R. Mazor, V. Khodorkovskii, L. Shapiro, J.T. Klug, E. Kovalev, G. Meshulam, G. Berkovic, Z. Kotler und S. Efrima
Title: Langmuir and Langmuir Blodgett films of NLO active 2-(p-N-alkyl-N-methylamino)benzylidene-1,3-indandione - p/A curves, UV-Vis spectra and SHG behavior
J. Phys. Chem. B Vol. 105, No. 25, p. 5914-5923 (2001); ISSN: 1089-5647; CODEN: JPCBFK


Abstract:
We study 2-(p-N-hexadecyl-N-methylamino)benzylidene-1,3-indandione (1a) as a model compound for the preparation of nonlinear optically (NLO) active Langmuir-Blodgett (LB) layers. The pressure-area (p-A) isotherm of (1a) at the air-water interface is investigated. A limiting area of 0.60 ± 0.02 nm2 per molecule is found. The alternate-layer LB deposition of compound (1a) and an inert spacer, cadmium stearate, at different surface pressures is performed. The effects of temperature and delay time between spreading of the Langmuir film and the deposition of the LB films are studied. An increase of collapse pressure from 20 to 30 mN/m is observed as the delay time increases. UV-Vis spectra indicate a uniform transfer of (1a) and show compression-induced changes as a function of the deposition conditions. A split of the absorption maximum is observed for LB films deposited at higher pressures and lower temperatures. The two bands can result from two different molecular electronic transitions, affected by the aligning influence of the surface, and the different environments in the film compared to solution. Alternatively, these two bands can be associated with (at least) two different conformers. The orientation of the transition moments is evaluated on the basis of polarized UV-Vis spectra at different angles of incidence, and found to be 40-44°. Significant second harmonic (SH) generation by the LB films is observed. Analysis of the SH response gives a tilt angle of 44°, in agreement with the finding from UV absorbance.


The 66th Annual Meeting of the Israel Chemical Society.
February 5-6, 2001,
David-Intercontinental Hotel, Tel-Aviv.

Author(s): C. Franz, G. Heinisch, W. Holzer, K. Mereiter, B. Strobl und C. Zheng
Title: Reaction products of 1,3-indandione with heteroaromatic carbaldehydes: synthesis, structure and NMR-investigations
Heterocycles Vol. 41, No. 11, p. 2527-2551 (1995); ISSN: 0385-5414; CODEN: HTCYAM


Abstract:
The synthesis of 1:1 condensation products from 1,3-indandione and various heteroaromatic carbaldehydes is described. Employment of aldehydes derived from n-deficient N-heteroaromatics was found to lead also to 2:1 adducts via Michael-addition of the 1,3-diketone to the initially formed 1:1 condensation products. 1H and 13C nmr spectroscopic studies of the products obtained and of known congeners are presented. The structure of the 2:1 adduct resulting from reaction of 1,3-indandione and 4-quinolinecarbaldehyde was determined by X ray analysis.

Author(s): S. Juršenas, V. Gulbinas, A. Gruodis, G. Kodis, V. Kovalevskij und L. Valkunas
Title: Spectroscopy of self-trapped charge-transfer excitons in polar films and crystals of N,N-dimethylaminobenzylidene 1,3-indandione (DMABI)
Phys. Chem. Chem. Phys. Vol. 1, No. 8, p. 1715-1718 (1999); ISSN: 1463-9076; CODEN: PPCPFQ


Abstract:
The origin of exciton states in crystals built up by dipolar N,N-dimethylaminobenzylidene-1,3-indandione (DMABI) molecules has been investigated by means of absorption and luminescence spectroscopy. The ecsiton spectral and dynamical properties in the solid state are compared to those of the excitation of separated DMABI molecules embedded in a rigid polymer matrix. The luminescence excitation spectra and the luminescence decay kinetics are discussed on the basis of the specific adiabatic potential-energy scheme of the self-trapped excitons.

Author(s): L.A. Chetkina, V.K. Bel'skii, E.G. Popova, B.P. Bespalov und A.G. Abolin
Title: X-ray diffraction structural study of 1,3-bis(dicyanomethylene)-2-(4'-(N,N-dimethylamino)phenylimino)indane
Zh. Strukt. Khim. Vol. 26, No. 5, p. 115-119 (1985); ISSN: 0044-4634; CODEN: ZSTKAI
J. Struct. Chem. (USSR) (Engl. Transl.) Vol. 26, No. 5, p. 748-751 (1985); ISSN: 0022-4766; CODEN: JSTCAM

Abstract:
The structural formula was determined for 1,3-bis(dicyanomethylene)-2-(4'-(N,N-diethylamino)phenylimino)indane in a diffractometric study. The unit cell parameters were a = 8.725, b = 8.238, c = 16.335 Angstroem, a = 74.50 °, b = 89.61 °, g = 69.60 °, space group P₁, Z = 2. A total of 1706 reflexions were recorded. The structure was solved by the direct method to R = 0.049. Due to steric factors, the electron-withdrawng dicyanomethyleneindane fragment and the electron-donor diethylaminophenyl fragment are twisted relative to each other such that dihedral angle between the indane and phenylene rings is 38.2 °. Bond length changes indicate intramolecular charge transfer. The five-membered ring of the indane system has envelope conformation, while the phenylene ring is a compressed boat. The dicyanomethylene groups have different twist angles (19.0 ° and 4.0 °).

Author(s): E.G. Popova, L.A. Chetkina, V.K. Bel'skii, B.P. Bespalov und A.G. Abolin
Title: Structure of the new acceptor 1,3-bis(dicyanomethylene)indan-2-one
Zh. Strukt. Khim. Vol. 24, No. 3, p. 128-132 (1983); ISSN: 0044-4634; CODEN: ZSTKAI
J. Struct. Chem. (USSR) (Engl. Transl.) Vol. 24, No. 3, p. 438-441 (1983); ISSN: 0022-4766; CODEN: JSTCAM

Abstract:
The crystal and molecular strucutre of the new acceptor 1,3-bis-(dicyanomethylene)-indan-2-one has been determined (a = 15.487 Å, b = 20.604 Å, c = 7.622 Å, g = 105.83 °, space group A2/a, Z = 8, diffractometer, 1493 reflections, direct method, R = 0.032). From the bond lengths and valence angles, the molecule has noncrystallogrphic symmetry relative to the line coinciding with the C=O bond. Because of steric hindrance and the influence of packing, the configuration of the molecule deviates considerably from planar. The most nearly planar fragment is the six-membered ring. The dicyanomethylene groups (including the C atoms of the five-membered ring joined to them) are displaced in different directions and to different extents away from the plane passing through the two C atoms common to the rings, and the carbonyl group, and simultaneously undergo rotation about the double bonds through angles of 6.1 and 5.6 °. The molecules in the crystal are packed in layers; a short contact of the C=O...C type is observed. It is also possible to distinguish stacks of molecules in the direction of the c axis.

Author(s): D. Citterioa, L. Jennya, S. Rásonyia und U.E. Spichiger
Title: Dyes for use in integrated optical sensors
Sensors and Actuators B: Chemical Vol. 39, No. 1-3, p. 202-206 (1997); ISSN: 0925-4005; CODEN: SABCEB

keywords: integrated optical sensors; near-infrared dyes; chromoionophores; plasticizers
Abstract:
In order to use chemically selective optode membranes in monolithically integrated optical sensors, the membrane's optical signal output ideally has to be in the near-infrared (NIR) wavelength range. Dyes showing light absorbance in the NIR range have been evaluated for their suitability as chromoionophores in plasticized poly(vinyl chloride) (PVC) membranes. The influence of the membrane plasticizer polarity on the optical properties and on the acidity of the dye has been investigated. It is shown that the pKa of the chromoionophore in the membrane phase can be shifted by changing the plasticizer polarity.

Entry no. 351
Author(s): V. Khodorkovsky und A. Ellern
Title: Molecular and crystal structures of donor-acceptor substitued polyenes involving 1,3-Indandione and Dibenzocycloheptenedione moieties
(1996); XVII Congress and General Assembly of the International Union of Crystallography, Seattle, Washington, USA, August 8-17, 1996

The XVII Congress and General Assembly of the International Union of Crystallography, 8-17 August , 1996 (Washington State Trade and Convention Center, Seattle Washington, USA)

http://www-ext.lmcp.jussieu.fr/iucr-top/cong/17/iucr/abstracts/title/06.00.html

Abstract:
E1150
MOLECULAR AND CRYSTAL STRUCTURES OF DONOR - ACCEPTOR SUBSTITUTED POLYENES INVOLVING 1,3-INDANDIONE AND DIBENZOCYCLOHEPTENEDIONE MOIETIES. Vladimir Khodorkovsky1, Arkady Ellern, Ben-Gurion University of the Negev, Chemistry Dept., P.O.B. 653, Beer Sheva, Israel.
Donor-acceptor substituted polyenes present currently a subject of numerous investigations due to their nonlinear optical properties. The importance of specific structural features in such chromophores for efficient second harmonics generation has been established, in particular, within the frame of bond length alternation (BLA) approach.
Derivatives involving the electron accepting moiety of 1,3-indandione and its structural analogs are often photoconducting and possess moderate to strong nonlinear optical properties. Many derivatives are distinguished by their ability to form several polymorphic modifications. For instance, for 2-(p-dimethylaminobenzylidene)-1,3-indandione, yellow-orange in solutions, two red and one blue polymorphs are known.
Recently we have synthesized a series of 2-ylidene 1,3-indandione and dibenzocycloheptenedione derivatives and determined their crystal structures. The deep color in solid state apparently can not be explained by enhanced intermolecular interactions and no considerable difference in BLA patterns has been found. The results of our crystallographic and quantum mechanical calculations which can explain the tendency for polymorphism and deep color in solid state within this class of compounds will be presented.

Author(s): K. Jacob, M. Sigalov, J.Y. Becker, A. Ellern und V. Khodorkovsky
Title: Self-condensation of 1,3-indandione: a reinvestigation
Eur. J. Org. Chem., No. 11, p. 2047-2056 (2000); ISSN: 1434-193X; CODEN: EJOCFK

keywords: 1,3-indandione; bindone; aldol condensation; truxenequinone; tribenzo[a,f,k]trindenone
Abstract:
The self-condensation of 1,3-indandione and bindone in pyridine and acetic acid has been reinvestigated. The structures of a number of products have been determined by analysis of their NMR spectra and by X-ray structure determination. The self-condensation of 1,3-indandione and bindone in pyridine and acetic acid has been reinvestigated. The structures of a number of products have been determined by analysis of their NMR spectra and by X-ray structure determination.

Author(s): V. Khodorkovsky, R. Mazor und A. Ellern
Title: 2-(p-Diethylaminobenzylidene)-1,3-indandione
Acta Crystallogr. Sect. C: Cryst. Struct. Commun. Vol. 52C, No. 11, p. 2878-2880 (1996); ISSN: 0108-2701; CODEN: ACSCEE


Abstract:
The title compound, C₂₀H₁₉NO₂, belongs to the class of donor-acceptor conjugated polyenes. Within the structure, O atoms are situated in the plane of the 1,3-indandione fragment and N atom lies in the plane of the p-benzylidene fragment which forms a dihedral angle of 7.6(2) ° with the indandione nucleus.

Author(s): N.S. Magomedova und Z.V. Zvonkova
Title: Crystal and molecular structure of the b-modification of 2-(p-dimethylaminobenzylidene)-1,3-indandione
Kristallografiya Vol. 25, No. 6, p. 1183-1187 (1980); ISSN: 0023-4761; CODEN: KRISAJ
Sov. Phys. Crystallogr. Vol. 25, No. 6, p. 677-679 (1980); ISSN: 0038-5638; CODEN: SPHCA6
keywords: X-ray structure of the b-modification of 2-(p-dimethylaminobenzylidene)-1,3-indandione
The b-modification of 2-(p-dimethylaminobenzylidene)-1,3-indandione was already published as abstract:
Abstracts of reports to the second All-Union Conference on Organic Crystal Chemistry [in Russian], Zvenigorod (1978), p. 102. Cited from citation no. 1 of Magomedova, N.S.; Zvonkova, Z.V.; Neigauz, M.G.; Novakoskaya, L.A.: Kristallografiya 25(2), 1980, 400-402 (engl. Transl: Sov. Phys. Crystallogr. 25(2), 1980, 230-232); compare also citation no. 6 of this publication.

Abstract:
In previous investigations we have shown that the highly conductive organic photosemiconductor 2-p-dimethylaminobenzylidene-1,3-indanedione forms three crystalline modifications; the crystal structure of the a modification was determined. An investigation of two modifications of this compound has established that the high photoconductivity of the crystals may be due both to intra- and intermolecular charge transfer (a modification) and to predominantly intramolecular charge transfer (b modification).

Author(s): N.S. Magomedova, Z.V. Zvonkova, L.S. Geita, L.M. Smelyanskaya und S.L. Ginzburg
Title: Crystal and molecular structure of 2-(4'-dimethylaminocinnamoyl)-1,3-indandione
Zh. Strukt. Khim. Vol. 21, No. 2, p. 131-136 (1980); ISSN: 0044-4634; CODEN: ZSTKAI
J. Struct. Chem. (USSR) (Engl. Transl.) Vol. 21, No. 2, p. 225-229 (1980); ISSN: 0022-4766; CODEN: JSTCAM

Abstract:
The structure of 2-(4'-dimethylaminocinnamoyl)-1,3-indanedione was determined by the method of non-local search for the minimum of a multiple variables function from diffractometric data up to R = 0.040. The enol structure of the molecule was stabilized by an intramolecular hydrogen bond. The type of packing of the molecules in the crystal without alternation of their donor and acceptor fragments is nontrivial for complexes with intramolecular charge transfer and, possibly, excludes the intermolecular charge transfer.

Author(s): N.S. Magomedova, Z.V. Zvonkova, L.S. Geita, L.A. Novakoskaya, M.G. Neigauz und V.K. Bel'skii
Title: Crystal and molecular structure of 2-(4'-dimethylaminophenylimino)-1,3-indandione
Zh. Strukt. Khim. Vol. 21, No. 6, p. 142-146 (1980); ISSN: 0044-4634; CODEN: ZSTKAI
J. Struct. Chem. (USSR) (Engl. Transl.) Vol. 21, No. 6, p. 809-812 (1980); ISSN: 0022-4766; CODEN: JSTCAM

Abstract:
In a continuation of a systematic x-ray structural study of autocomplexes with charge transfer, in which the acceptor fragment is 1,3-indanedione, and the donor fragment is dimethylaniline, the crystal and molecular structure of 2-(4'-dimethylaminophenylimino)-1,3-indanedione has been studied (diffractometer, lMo, 1054 reflections, method of steepest descents, anisotropic refinement, R = 0.031). The molecule is almost planar. The transfer of charge influences the structure of the five-membered ring and the diaminobenzene part of the molecule. A weak intramolecular hydrogen bond C -H . . . O has been detected. The crystal is made up of layers of the donor and acceptor fragments of the molecule, alternating along the c axis; this method of packing is characteristic of autocomplexes.

Author(s): E. Gudriniece, A. Ievins, G. Vanags, V. Brunere und J. Bankovskis
Title: Sulfonation of b-diketones - IX. 1,3-Indanedione-2,2-disulfonic acid and its salts
Latvijas PSR Zinatnu Akad. Vestis, No. 3, p. 103-109 (1960); ISSN: 0023-8929; CODEN: LZAVAL

Author(s): E. Gudriniece, A. Ievins, G. Vanags und D. Kreicberga
Title: Sulfonation of b-diketones - XV. Bindonesulfonic acid and its salts
Latvijas PSR Zinatnu Akad. Vestis, No. 2, p. 111-114 (1961); ISSN: 0023-8929; CODEN: LZAVAL

Author(s): E. Gudriniece, E. Dreimanis und G. Vanags
Title: Sulfonation of b-diketones by dioxane-sulfur trioxide - I
Dokl. Chem. (Engl. Transl.) Vol. 110, No. 1-6, p. 601-603 (1956); ISSN: 0012-5008; CODEN: DKCHAY
Dokl. Akad. Nauk. SSR, Ser. Khim. Vol. 110, No. 5, p. 786-788 (1956); ISSN: 0002-3264; CODEN: DASKAJ
keywords: sodium 1,3-indandione-2-sulfonate

Author(s): E. Gudriniece, A. Ievins und G. Vanags
Title: Sulfonation of b-diketones by dioxane-sulfur trioxide. II. 1,3-Indandione-2-sulfonic acid and its salts
J. Gen. Chem. USSR Vol. 28, No. 1, p. 95-100 (1958); ISSN: 0022-1279; CODEN: JGCHA4
Zh. Obshch. Khim. Vol. 28, No. 1, p. 95-100 (1958); ISSN: 0044-460X; CODEN: ZOKHA4

Author(s): E. Gudriniece und G. Vanags
Title: Cyclic arylazo-b-diketones. I. Condensation of 1,3-Indandione with diazo compounds
J. Gen. Chem. USSR Vol. 28, No. 1, p. 59-63 (1958); ISSN: 0022-1279; CODEN: JGCHA4
Zh. Obshch. Khim. Vol. 28, No. 1, p. 58-62 (1958); ISSN: 0044-460X; CODEN: ZOKHA4

Author(s): E. Gudriniece, A. Ievins, G. Vanags, L. Natale und D. Kreile
Title: Cyclic arylazo-b-diketones. V. Metal complexes of 2-phenylazo-1,3-indandione
Latvijas PSR Zinatnu Akad. Vestis, No. 10, p. 107-113 (1959); ISSN: 0023-8929; CODEN: LZAVAL

Author(s): E. Gudriniece, G. Vanags und L. Sakhar
Title: Condensation of the sodium salt of ethyl-1,3-indandione-2-carboxylate with diazotized nitroanilines
Dokl. Chem. (Engl. Transl.) Vol. 129, p. NIE 89: ZZ 38/1:che [Haus 2] (1959); ISSN: 0012-5008; CODEN: DKCHAY
Dokl. Akad. Nauk. SSR, Ser. Khim. Vol. 129, p. 1182-1184 (1959); ISSN: 0002-3264; CODEN: DASKAJ

Author(s): E. Gudriniece und G. Vanags
Title: New method for the preparation of 2-nitro-1,3-indandione
Khim. Nauka i. Prom. Vol. 4, p. 683-684 (1959); ISSN: 0368-5586; CODEN: KHNPAX

Author(s): G. Vanags und I. Stunda
Title: 2-Nitro-4,5-dimethoxy-1,3-indandione
Latvijas PSR Zinatnu Akad. Vestis, No. 3, p. 77-84 (1960); ISSN: 0023-8929; CODEN: LZAVAL

Author(s): L. Zalukajevs
Title: Addition reactions of 1,3-Indandione and its nitro derivative at the double bond
J. Gen. Chem. USSR Vol. 26, No. 11, p. 3483-3490 (1956); ISSN: 0022-1279; CODEN: JGCHA4
Zh. Obshch. Khim. Vol. 26, No. 11, p. 3125-3132 (1956); ISSN: 0044-460X; CODEN: ZOKHA4

Abstract:
The addition reaction of Indandione-1,3 and 2-nitroindandione-1,3 to some unsaturated compounds has been described. The structure of the compounds obtained has been proved.

Author(s): S. Juršenas, V. Kovalevskij, A. Groudis, G. Kodis, L. Valkunas, I. Mazikante und E.A. Silinsh
Title: Exciton-phonon interaction in polar organic crystals
Liet. Fiz. Zh. Vol. 37, No. 6, p. 567-571 (1997); ISSN: 1392-1932; CODEN: LFZUE7
Lith. J. Phys. Vol. 37, No. 6, p. 567-571 (1997);

Abstract:
Manifestation of strong exciton-phonon coupling in the absorption and luminescence spectra of polar molecular crystals of dimethylaminobenzylidene indandione-1,3 (DMABI) and indandione-1,3 pyridinium betaine (IPB) is demonstrated. Exciton-phonon coupling values g - 1.87 and g - 1.91 for DMABI and IPB, respectively, are estimated from the absorption slope at the low energy edge (the Urbach edge). This estimation together with the Stokes-shift data allows the authors to conclude that half of the exciton bandwidth has to be equal to B = 0.125 eV and the lattice relaxation energy ELR = 0.235 eV for the DMABI crystal. From the proposed potential energy diagram, two kinds of the self-trapped exciton formation in polar molecular crystals are discussed.

Author(s): S. Juršenas, A. Gruodis, G. Kodis und L. Valkunas
Title: Spectroscopy of excitons in the polar molecular crystal DMABI
Adv. Mater. Opt. Electron. Vol. 6, No. 5&6, p. 387-390 (1996); ISSN: 1057-9257; CODEN: AMELE7


Abstract:
The origins of the excited states and spectroscopic features of polar molecular compounds of N,N-dimethylaminobenzylidene-1,3-indandione (DMABI) were investigated. Evidence of a strong exciton-phonon interaction and its effects on the exciton absorption and luminescence spectra was discovered. The spectral features were related to the crystal structure and were ascribed to self-trapped charge transfer excitons. A weak, narrow luminescence line was also observed in resonance with the lowest absorption band and was attributed to free exciton radiative recombination.

Author(s): C. Sentein, C. Fiorini, A. Lorin, J.-M. Nunzi und L. Sicot
Title: Poling induced improvement of organic polymer device efficiency
Synth. Metals Vol. 102, No. 1-3, p. 989-990 (1999); ISSN: 0379-6779; CODEN: SYMEDZ

keywords: solar cells; spin-cast semiconducting films; semiconducting films; organic semiconductors based on cunjugated molecules
Abstract:
In order to build single polymer film photovoltaic cells, we realize an equivalent distributed PN junction in a polymeric monolayer. Orientation is performed through DC-field ordering of the polar molecules contained in the polymer. We describe experimentallly an increase by one order of magnitude for the effciency of our photovoltaic cell by polar ordering of the molecules.

Author(s): H. Hashimoto, K. Hattori, T. Yamada und T. Kobayashi
Title: Electro-absorption spectroscopy and semi-empirical molecular orbital calculations of polar retinoid analogues
Int. J. Modern Phys. B Vol. 15B, No. 28-30, p. 3773-3777 (2001); ISSN: 0217-9792; CODEN: IJPBEV

keywords: 2-Retinyl-1,3-bis(dicyanmethylene)-indane
Abstract:
Nonlinear polarizabilities of a series of polar retinoid analogues were determined experimentally by means of electro-absorption (Stark) spectroscopy. The dependence of the magnitude of nonlinear polarizabilities on polyene chain-lengths as well as on the strength of electron-accepting groups was systematically compared. Semi-empirical molecular orbital calculations using AM1 Hamiltonian (MNDO-AM1 method) could quantitatively predict the second (b) and the third (g) order nonlinear polarizabilities of the present set of molecules except for the g value of C20BDCInd. The real and imaginary parts of c(3)(-w;0,0,w) spectra were calculated in order to account the figure of merit of the third-order nonlinear optical material.

Author(s): T. Uyar
Title: The reactions of indandiones with active methylene compounds
Commun. Fac. Sci. Univ. Ankara, Ser. B (Chem. & Chem. Engineering) Vol. 34, No. 1-2, p. 135-140 (1988); ISSN: 0570-1414; CODEN: CAKBA9


Abstract:
We have studied the reactions of 1,3-indandione (1), 2-methyl-1,3-indandione (II) and 2,2-dimethyl-1,3-indandione (III) with malononitrile and methyl cyanoacetate. Both, I and II, reacted with malononitrile to give several compounds. The reaction of methyl cyanoacetate with I gave a dark, resinous material under similar conditions, while II gave mono imine of the indandione in poor yield. The reaction of III with malononitrile and methyl cyanoacetate did not take place. The structure of the compounds were confirmed on the basis of IR, UV, ¹H-NMR and mass spectral studies.

Author(s): A.A. Ishchenkeo, N.A. Derevyanko, S.V. Popov, Y.L. Slominskii, V.L. Koval', S.A. Shapovalov und N.O. Mchedlov-Petrosyan
Title: Interaction of chromophores in dissimilar associates of cationic and anionic polymethine dyes in water
Izv. Akad. Nauk., Ser. Khim. Vol. 46, No. 5, p. 950-955 (1997); ISSN: 0002-3353; CODEN: IASKEA
Russ. Chem. Bull. Vol. 56, No. 5, p. 910-915 (1997); ISSN: 1066-5285; CODEN: RCBUEY
keywords: cationic and anionic poIymethine dyes; interaction of chromophores; cation-anionic associates; association constants; electronic absorption spectra
Abstract:
A strong interaction between chromophores of cationic and anionic components was found based on the analysis of electronic absorption spectra of aqueous solutions of mixtures of cationic indopolycarbocyanines with anionic cyanines. Stong dissimilar 1:1 associates are formed. Association constants were estimated spectrophotometrically. The main factors determining the degree of interaction of chromophores were revealed.

Author(s): L.A. Chetkina, V.E. Zavodnik, A.N. Sobolev, V.K. Bel'skii, B. Bespalov und A.G. Abolin
Title: Structure of the crystal solvate of the dipyridinium salt of 2,2'-bis[1,3-bis(dicyanomethylene)indane] with acetonitrile
Zh. Strukt. Khim. Vol. 32, No. 3, p. 141-144 (1991); ISSN: 0044-4634; CODEN: ZSTKAI
J. Struct. Chem. (USSR) (Engl. Transl.) Vol. 32, No. 3, p. 442-445 (1991); ISSN: 0022-4766; CODEN: JSTCAM

Abstract:
This communication gives the results of the crystal solvate of the dipyridinium salt of 2,2'-bis[1,3-bis(dicyanomethylene)indane] with acetonitrile, measured as a cut sample of 0.12 x 0.17 x 0.4 mm of a single crystal. Obtained 2201 independent reflections, the data for the monoclinic title compound are as follows: M = 681.7; a = 7.755(2) Å; b = 24.556(6) Å; c = 19.368(5) Å; g = 106.31(2) °; V = 3540(1) ų; Z = 4; space group P2₁/^b. The structure was solved by direct methods and refined by least-squares to R = 0.051. The H-bonding is described. The difference to other modifications of the molecule is discussed.

Author(s): R. Benassi, C. Bertarini, F. Taddei und E. Kleinpeter
Title: Exocyclic push-pull conjugated compounds. Part 4. Rotational barriers in poorly polarized push-pull ethylenes
J. Mol. Struct. (Theochem.) Vol. 541, No. 1-3, p. 101-110 (2001); ISSN: 0166-1280; CODEN: THEODJ

keywords: Push-pull ethylenes; MO ab initio calculations; MCSCF theory; Rotational barriers; Heterocyclic derivatives; Conformations
Abstract:
The rotational barrier for substituted ethylenes was calculated with MO ab initio methods, both in the Hartree–Fock (HF) single determinant scheme and with multiconfigurational self-consistent field (MCSCF) approaches. The HF model affords reliable results only when applied to molecules substituted with strong electron donor groups, assigning a push–pull character to the molecule. The MCSCF approach was employed for calculating rotational barriers in poorly polarized ethylenes not directly amenable to the HF methods; however, this method was found hard to handle for low symmetry molecules with substituents interacting with the double bond. A method is proposed based on the interpolation of the energy of the perpendicular conformation from a Fourier truncated function constructed with HF molecular energies calculated for frozen conformations twisted up to 60°. The application of HF theory for studying internal rotation in substituted ethylenes with poorly polarized character is discussed and an upper limit of 35–40 kcal/mol can be set up for having reliable barriers from the calculated energy of the rotational transition state at this level of theory.

Author(s): A.C. Capomacchia und S.G. Schulman
Title: Confirmation of iminoacridan structure of singly protonated 9-aminoacridine
J. Pharm. Sci. Vol. 64, No. 7, p. 1256-1257 (1975); ISSN: 0022-3549; CODEN: JPMSAE

keywords: 9-Aminoacridine; singly protonated; confirmation of iminoacridan structure; Iminoacridan-confirmed as structure of singly protonated 9-aminoacridine; Acridine derivatives; confirmation of iminoacridan structure of singly protonated 9-aminoacridine
Abstract:
The occurrence of the second absorption band of singly protonated 9-aminoacridine, which arises from an acridinium ring-localized transition, at anomalously short wavelength indicates the disruption of the aromaticity of the central ring of the singly charged cation. The shifting of the two longest wavelength absorption bands and the fluorescence band of 10-methyl-9-aminoacridine monocation, a model of singly protonated 9-aminoacridine which is constrained to dissociate from the exocyclic nitrogen atom, to shorter wavelengths, upon dissociation, indicates the imine-like nature of the 10-methyl derivative. These observations support the conclusion that the predominant site of positive charge in singly protonated 9-aminoacridine is the exocyclic nitrogen atom, even though the heterocyclic nitrogen atom is the site of protonation of the neutral molecule.

Author(s): S. Eskola
Title: The action of NaOMe on the lactones of g-keto acids. Formation of 1,3-dioxacyclopentanes
Suomen Kemistilehti [B] Vol. 15, p. 17-19 (1942); ISSN: 0371-4101; CODEN: SUKBAJ

Author(s): F. Canziani, M.C. Malatesta und G. Longoni
Title: Iridium-maleoyl complexes from tricarbonyliridium halides and acetylenes
J. Chem. Soc. Chem. Commun., p. 267-268 (1975); ISSN: 0022-4936; CODEN: JCCCAT

keywords: 2,3-Diphenylmaleinic acid; 2,3-Diphenylmaleinic acid anhydride; 2,3-Dimethylmaleinic acid; 2,3-Dimethylmaleinic acid anhydride

Author(s): Robin D. Allan und Joyce Fong
Title: Synthesis of analogues of GABA. X. The bicyclic b-diketone octahydro-1H-2-pyrindine-5,7-dione
Aust. J. Chem. Vol. 36, No. 6, p. 1221-1226 (1983); ISSN: 0004-9425; CODEN: AJCHAS


Abstract:
The synthesis is described of octahydro-2(1H)-pyrindin-5,7-dione (4) and its 6-diazo and 6-bromo derivatives. These are analogues of GABA in which the carboxyl group is replaced by an enolic b-diketone. The compounds showed negligible or very weak activity as GABA agonists with respect to inhibition of (3H)GABA binding, uptake and transamination in rat brain membranes.

Author(s): C. Ruangsiyanand, H.-J. Rimek und F. Zymalkowski
Title: Enamine cyclischer 1,3-Diketone als Ausgangsstoffe für Pyridinsynthesen
Chem. Ber. Vol. 103, p. 2403-2410 (1970); ISSN: 0009-2940; CODEN: CHBEAM

keywords: 6,7-Dihydro-1(5H)-pyrindin-5-one; 4-Aza-1-indanone

Author(s): Y. Huang und R.W. Hartmann
Title: The improved preparation of 7,8-Dihydroquinoline-5(6H)-one and 6,7-Dihydro-5H-1-pyrindin-5-one
Synth. Commun. Vol. 28, No. 7, p. 1197-1200 (1998); ISSN: 0039-7911; CODEN: SYNCAV

keywords: 6,7-Dihydro-1(5H)-pyrindin-5-one; 4-Aza-1-indanone

Author(s): D. Binder
Title: Preparation of Ethyl 3-Hydroxy-1-methyl-4-oxo-1,4-dihydropyrrolo[2'.3':3.4]cyclopenta[1.2-c]pyridine-2-carboxylate. A new heterocyclic ring system.
Monatsh. Chem. Vol. 105, p. 179-186 (1974); ISSN: 0026-9247; CODEN: MOCMB7

keywords: 1-Pyrindin-5,7-dione-2-carboxylic acid ethylester; 4-Aza-1,3-indandione
Abstract:
4 is synthesized starting from 1 over the chloride 3 and then cyclized by Dieckmann condensation to the title compound 8. The structure of 4 is confirmed by chemical proof. By means of ¹H-NMR-spectral analysis it could be determined that 1 exists as internal salt (2a) of ethyl 5-hydroxy-7-oxo-7H-1-pyrindin-6-carboxylate.

Author(s): D. Binder
Title: Preparation of Ethyl 3-Hydroxy-1-methyl-4-oxo-1,4-dihydropyrrolo[2'.3':3.4]cyclopenta[1.2-c]pyridine-2-carboxylate. A representative of a new heterocyclic ring system
Monatsh. Chem. Vol. 105, p. 196-202 (1974); ISSN: 0026-9247; CODEN: MOCMB7

keywords: 1-Pyrindin-5,7-dione-2-carboxylic acid ethylester; 4-Aza-1,3-indandione
Abstract:
The reaction of cinchomeronic anhydride with diethyl malonate in acetic anhydride in the presence of triethylamine yields 1, which is hydrogenated over Pd/C (10 %) in dry benzene to 2. The structures of 1 and 2 are confirmed by IR- and 1H-NMR-spectra. 1 can be reduced to 3 with Zn in acetic acid. Hydrolysis of 3 yields 4, which is easily decarboxylated to 5. Methylation of 5 with diazo methane gives 6. The 1H-NMR-spectrum of 6 makes a definite structural assignment possible. 6 undergoes a Dieckmann cyclisation to 7, which forms 8 on heating in water, and the title compound 9 on heating in 4n-HCl.

Author(s): D. Binder
Title: Preparation of Ethyl 3-Hydroxy-1-methyl-4-oxo-1,4-dihydropyrrolo[2'.3':3.4]cyclopenta[1.2-c]pyridine-2-carboxylate. A representative of a new heterocyclic ring system
Monatsh. Chem. Vol. 105, p. 203-208 (1974); ISSN: 0026-9247; CODEN: MOCMB7

keywords: 1-Pyrindin-5,7-dione-2-carboxylic acid ethylester; 4-Aza-1,3-indandione
Abstract:
A representative of a new heterocyclic ring system 1 is synthesized by reaction of cinchomoronic anhydride with ethyl acetoacetate and triethylamine in acetic anhydride. Its structure is discussed by means of IR- and 1H-NMR-spectrum. By reaction of 1 with SOCl₃ 3 is formed, which is converted with ethyl sarcosinate to 4. The structure of 4 is confirmed by chemical proof. Dieckmann cyclisation of 4 gives the title compound 7.

Author(s): W.A. Mosher, T. Tawfik El-Zimaity und D.W. Lipp
Title: 6-Acyl-1(5H)-pyrindin-5,7(6H)-diones and their reaction with hydrazine
J. Org. Chem. Vol. 36, No. 25, p. 3890-3894 (1971); ISSN: 0022-3263; CODEN: JOCEAH

keywords: 1-Pyrindin-5,7-dione-2-carboxylic acid ethylester; 4-Aza-1,3-indandione; dimethyl 2,3-pyridinedicarboxylate; 2,3-pyridinedicarboxylic acid dimethylester; Quinolinic acid dimethylester; Quinolineacid dimethylester
Abstract:
A series of 6-acyl-1(5H)pyrindin-5,7(6H)-diones (1) were prepared by condensing dimethyl 2,3-pyridinedicarboxylate with various methyl ketones. Depending upon the conditions, reaction of compounds 1 with hydrazine gave 3-substituted 1,4-dihydropyrazolo[3',4': 3,4]cyclopenta[1,2-b]pyridines (6), 3-substituted pyrazolo[3',4':3,4]cyclopenta[ 1,2-b]pyridin-4(1H)-ones (2), or a mixture of the hydrazones of the two isomeric 3-substituted pyrazolo[3',4': 3,4]cyclopentapyridin-4(1H)-ones (4 and 5).

Author(s): W.A. Mosher und D.W. Lipp
Title: Reactions of 6-acyl-5H-1-pyrindine-5,7(6H)-diones with diamines
J. Org. Chem. Vol. 37, No. 20, p. 3190-3192 (1972); ISSN: 0022-3263; CODEN: JOCEAH

keywords: 1-Pyrindin-5,7-dione-2-carboxylic acid ethylester; 4-Aza-1,3-indandione; dimethyl 2,3-pyridinedicarboxylate; 2,3-pyridinedicarboxylic acid dimethylester; Quinolinic acid dimethylester; Quinolineacid dimethylester

Author(s): U. Westerwelle, A. Esser und N. Risch
Title: b-Amino Ketones as key intermediates in the synthesis of pyridines: a novel and efficient route to annelated Bi- and Terpyridines
Chem. Ber. Vol. 124, p. 571-576 (1991); ISSN: 0009-2940; CODEN: CHBEAM

keywords: Annelated pyridines; preparation from Mannich bases; substituted 5,6-Dihydro-1,10-phenanthrolines; substituted 4,5-Diazafluorenes; 5,6-Dihydro-1(7H)-pyrindin-7-one; 2-Aza-1-indanone; 6,7-Dihydro-8(5H)-quinolinone
Abstract:
The hydrochlorides of b-amino ketones 1 a - e (Mannich bases) are easily obtained starting compounds for a novel synthesis and of pyridines. Condensation with the heteroaromatic ketones 8, 9 and 10 yields 5,6-dihydro-1,10-phenanthrolines 3a - d, 13 and 4,5-diazafluorenes 4a - d, which have not yet been described in literature. Symmetrical terpyridines 3e, 4e are formed in a one-step reaction of 8, 9 with dimethylmethylen ammonium chloride in the presence of an ammonia source.

Author(s): B.W. Caprathe, J.C. Jaen, L.D. Wise, T.G. Heffner, T.A. Pugsley, L.T. Meltzer und M. Parved
Title: Dopamine autoreceptor agonists as potential antipsychotics. 3. 6-propyl-4,5,5a,6,7,8-hexahydrothiazolo[ 4,5-f ]quinolin-2-amine
J. Med. Chem. Vol. 34, p. 2736-2746 (1991); ISSN: 0022-2623; CODEN: JMCMAR

keywords: 5,6-Dihydro-1(7H)-pyrindine; 6,7-Dihydro-(5H)-cyclopenta[b]-pyridin-5ne; 4-Aza-1-indanone; 7,8-Dihydro-5(6H)-quinolinone; 6-Bromo-7,8-dihydro-5(6H)-quinolinone; 7,8-Dihydro-5(6H)-isoquinolinone; 6,7-Dihydro-8(5H)-isoquinolinone
Abstract:
A series of rigid tricyclic analogues of the dopamine (DA) agonist PD 118440 [4-(1,2,5,6-tetrahydro-1-propyl-3-pyridinyl)-2-thiazolamine] was synthesized and evaluated for dopaminergic activity and DA autoreceptor selectivity. (R)-(+)-6-Propyl-4,5,5a,6,7,8-hexahydrothiazolo[4,5-f]quinolin-2-amine ((+)-6) was identified as the most selective DA autoreceptor agonist from this group of compounds. It inhibited spontaneous locomotor activity (LMA) in rodents, reversed the g-butyrolactone (GBL) induced accumulation of rat striatal DOPA and inhibited brain DA neuronal firing, all suggestive of direct DA autoreceptor agonist activity. However, (+)-6 is not completely free of postsynaptic DA activity, as evidenced by its stimulation of LMA in rats at high doses and its ability to produce stereotypy. On the other hand, (-)-6 appears to be a weak partial DA agonist with some effects on brain DA synthesis only at high doses. Like other DA autoreceptor agonists and DA antagonists, (+)-6 inhibited Sidman conditioned avoidance in squirrel monkeys, a test predictive of clinical antipsychotic activity. However, unlike classical antipsychotics, (+)-6 did not induce dystonias in haloperidol-sensitized squirrel monkeys, suggesting a minimal propensity toward extrapyramidal side effects (EPS).

Author(s): E.C. Taylor, J.E. Loeffler und B. Mencke
Title: A synthesis of 5-chloro-6-ethoxypyrimindines
J. Org. Chem. Vol. 28, p. 509-511 (1963); ISSN: 0022-3263; CODEN: JOCEAH


Abstract:
Condensation of ethyl a-chIoro-b,b-diethoxyacrylate with amidines in the presence of sodium ethoxide has been found to give 2-substituted 4-hydroxy-5-chloro-6-ethoxypyrimidines in high yield. An intermediate conjugate addition compound, ethyl a-chloro-b,b-diethoxy-b-guanidinopropionate (IX), was isolated when guanidine was employed. An analogous series of 2-substituted 4-amino-5-chloro-6-ethoxypyrimidines was prepared by the condensation of a,b,b-trichloroacrylonitrile or the imino ether of a-chloro-b,b-diethoxyacrylonitrile with amidines . These 5-chloro-6-ethoxypyrimidines did not react further with amidines to give purines.

Author(s): L.E. Neilands und G. Vanags
Title: Some derivatives of 4-azaindandione-1,3
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 1, p. 74-78 (1963); ISSN: 0002-3248; CODEN: LZAKAM

keywords: 1-Pyrindin-5,7-dione-2-carboxylic acid methylester; 4-Aza-1,3-indandione; 6-Benzylidene-1-pyrindin-5,7-dione; 2-Benzylidene-4-aza-1,3-indandione; 6-(4-nitrobenzylidene)-1-pyrindin-5,7-dione; 2-(4-nitrobenzylidene)-4-aza-1,3-indandione
Abstract:
1. The sodium salt of 2-carbomethoxy-4-azaindanedione-1,3 has been prepared by means of an improved method.
2. On the basis of IR absorption spectra it is presumed that 2-carbomethoxy-4-azaindanedione-1,3 exists in the form of an internal salt.
3. The copper complex and N-methylbetaine of 2-carbomethoxy-4-azaindanedione-1,3 as well as 2-benzal- and 2-(p-nitrobenzal)-4-azaindanedione-1,3 have been obtained.
4. IR absorption spectra of the 4-azaindanedione-2,3 derivatives have been produced and their electronic structure is discussed.

Author(s): V. Oskaja und G. Vanags
Title: Condensation of dicarboxylic acid anhydrides with compounds containing active methylene groups. I. Condensation of phthalic anhydride with acetoacetic and malonic ester
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 3, p. 271-276 (1964); ISSN: 0002-3248; CODEN: LZAKAM


Abstract:
When phthalic anhydride was condensed with acetoacetic ester in acetic anhydride and triethylamine solution as well as when phthalyl chloride was reacted with sodium-acetoacetic ester, compounds of the phthalide and indanedione series were formed: phthalyl-acetoacetic ester and a derivative of indanedione-1,3 which after boiling with hydrochloric acid yielded indanedione-1,3. From phthalic anhydride and malonic ester in acetic anhydride in the presence of triathylamine, phthalyl-malonic ester was obtained.

Inventor(s): T.-L. Shen und R. Greenwald
Title: Antiinflammatory azaindene-3-aliphatic acids
(Merck and Co., Inc.) German Pat. Appl. DE 2,020,762, (12.11.1970); Patent Class.: C 07d
CODEN: GWXXBX

Abstract:
The title compounds I (R = H or Cl, R1 = H ) were prepared from 5-chloro-2-carbethoxy-4-aza-1-indanone (II). II was methylated with MeI-EtONa to give 5-chloro-2-methyl-2-carbethoxy-4-aza-1-indanone which was hydrolyzed (HCI) to give 5-hydroxy-2-methyl-4-aza-1-indanone (III). III was chlorinated with POCI₃ and treated with BrCH₂CO₂Me in the presence of Zn-I to give Methyl (5-chloro-2-methyl-1-hydroxy-4-aza-1-indanyl)acetate (IV). Dehydration of IV with P₂O₅ gave a mixture of Methyl (6-chloro-2-methyl-7-aza-3-indenyl)acetate and Methyl (5-chIoro-2-methyl-4-aza-1-indanylidene)acetate: the mixture was treated with p-CIC₆H₄CHO and NaOMe to give I (R = Cl, R' = Me) which an hydrolysis (KOH) gave I (R = Cl, R' = H ). Catalytic hydrogenation (Pd-C) of IV gave Methyl (2-methyl-1-hydroxy-4-aza-1-indanyl)acetate which was similarly dehydrated and converted into I (R = R' = H). Ethyl 6-hydroxy-2-methyl-nicotinate was chlorinated with POCl₃ and brominated with N-bromosuccinimide to give Ethyl 6-chloro-2-(bromomethyl)-nicotinate which was contdensed with NaCH(CO₂Et)₂ to give Ethyl 6-chloro-2-(2,2-dicarbethoxy)-ethylnicotinate (V). V on treatment with KSMe gave Ethyl 6-methylthio-2-(2,2-dicarbethoxy)-ethylnicotinate which was cyclized with NaH to give the azaindanone ester VI.

Author(s): K. Bittner
Title: Synthese von Pyrindenderivaten
Ber. dtsch. Chem. Ges. Vol. 35, p. 1411-1413 (1902); ISSN: 0365-9496; CODEN: BDCGAS

Author(s): E. Ochiai, K. Miyaki und S. Sato
Title: Synthese von 2,5-Naphthyridin-Derivaten
Ber. dtsch. Chem. Ges. Vol. 70, No. 9, p. 2018-2023 (1937); ISSN: 0365-9496; CODEN: BDCGAS

Author(s): S. Blumenfeld
Title: Über Chinchomeronsäurederivate
Monatsh. Chem. Vol. 16, p. 693-720 (1895); ISSN: 0026-9247; CODEN: MOCMB7

keywords: chinchomeronic acid; pyridine-3,4-dicarboxylic acid; pyridine-3,4-dicarboxylic acid diethylester

Author(s): A. Kirpal
Title: Über die Ester der Chinolinsäure und Chinchomeronsäure
Monatsh. Chem. Vol. 20, p. 766-778 (1899); ISSN: 0026-9247; CODEN: MOCMB7

keywords: chinchomeronic acid; pyridine-3,4-dicarboxylic acid; pyridine-3,4-dicarboxylic acid diethylester; chinolinic acid; pyridine-2,3-dicarboxylic acid; pyridine-2,3-dicarboxylic acid diethylester; 3,4-pyridinedicarboxylic acid; 3,4-pyridinedicarboxylic acid diethylester; diethyl-2,3-pyridinedicarboxylate; diethyl-3,4-pyridinedicarboxylate

Author(s): K. Kaas
Title: Über Chinchomeron- und Apophyllensäure
Monatsh. Chem. Vol. 23, p. 250-261 (1902); ISSN: 0026-9247; CODEN: MOCMB7

Author(s): B. Fels
Title: Abkömmlinge der Chinchomeronsäure
Ber. dtsch. Chem. Ges. Vol. 37, p. 2137-2149 (1904); ISSN: 0365-9496; CODEN: BDCGAS

keywords: chinchomeronic acid; pyridine-3,4-dicarboxylic acid; pyridine-3,4-dicarboxylic acid diethylester; 3,4-pyridinedicarboxylic acid diethylester; diethyl-2,3-pyridinedicarboxylate; diethyl-3,4-pyridinedicarboxylate; 2-benzylidene-5-aza-1,3-indandione; 6-benzylidene-2-pyrindin-5,7-dione

Author(s): A. Philips
Title: Untersuchungen in der Pyridinreihe
Justus Liebigs Ann. Chem. Vol. 288, p. 253-265 (1895); ISSN: 0075-4617; CODEN: JLACBF

keywords: chinolinic acid; pyridine-2,3-dicarboxylic acid; 2,3-pyridinedicarboxylic acid

Author(s): H. Strache
Title: Zur Kenntnis der Orthodicarbonsäuren des Pyridins
Monatsh. Chem. Vol. 11, p. 133-148 (1890); ISSN: 0026-9247; CODEN: MOCMB7

keywords: chinchomeronic acid; pyridine-3,4-dicarboxylic acid; 3,4-pyridinedicarboxylic acid; 3,4-pyridinedicarboxylic acid diethylester; monoethyl-2,3-pyridinedicarboxylate; diethyl-3,4-pyridinedicarboxylate; 3,4-pyridinedicarboxylic acid monoethylester; chinchomeronic acid anhydride

Author(s): G. Goldschmiedt und H. Strache
Title: Zur Kenntnis der Orthodicarbonsäuren des Pyridins
Monatsh. Chem. Vol. 10, p. 156-160 (1889); ISSN: 0026-9247; CODEN: MOCMB7

keywords: chinchomeronic acid; pyridine-3,4-dicarboxylic acid; 3,4-pyridinedicarboxylic acid; 3,4-pyridinedicarboxylic acid diethylester; monoethyl-2,3-pyridinedicarboxylate; diethyl-3,4-pyridinedicarboxylate; 3,4-pyridinedicarboxylic acid monoethylester; chinchomeronic acid anhydride

Author(s): A. Bernthsen und H. Mettegang
Title: Über einige Reaktionen der Chinolinsäure
Ber. dtsch. Chem. Ges. Vol. 20, p. 1208-1210 (1887); ISSN: 0365-9496; CODEN: BDCGAS

keywords: chinolinic acid; pyridine-2,3-dicarboxylic acid; 2,3-pyridinedicarboxylic acid

Author(s): M.L. de Winter und W.T. Nauta
Title: Pharmacochemistry of 2-diarylmethyl-1,3-indandiones. I. Synthesis
Eur. J. Med. Chem. Vol. 12, No. 2, p. 125-130 (1977); ISSN: 0223-5234; CODEN: EJMCA5


Abstract:
A number of 2-diarylmethyl-1,3-indandiones is synthesized either by condensation of 1,3-indandione with a (substituted) diphenylmethanol or by 1,4-addition of an aromatic Grignard compound to a (substituted) 2-benzylidene-1,3-indandione. The synthesis of phthaloyl substituted compounds in this series is achieved via the corresponding ethyl 1,3-dioxo-2-indancarboxylate. Some new 2-benzylidene-1,3-indandiones are prepared. The condensation reaction is extended to some 3-diarylmethyl-4-hydroxycournarins. A few orfho-substituted title compounds are obtained as their oxidation products: 3-diarylmethylene-1,4-isochromandione. Some carboxylic esters of 2-benzhydryl-1,3-indandione and 3-benzhydryl-4-hydroxycoumarin are synthesized.

Author(s): M.L. de Winter und W.T. Nauta
Title: Pharmacochemistry of 2-diarylmethyl-1,3-indandiones. II. Keto-enol tautomerism and NMR-spectroscopy
Eur. J. Med. Chem. Vol. 12, No. 2, p. 131-136 (1977); ISSN: 0223-5234; CODEN: EJMCA5


Abstract:
The keto-enol tautomerism of 2-diarylmethyl-1,3-indandiones strongly depends on the degree of ortho-substitution of the diarylmethyl group. Where f. i. four ortho-substituents are present, the compounds occur in the enol form only. IR spectroscopy of the latter compounds reveals intramolecular hydrogen bonding. Inspection of coupling constants of the vicinal aliphatic protons in the NMR-spectra of the title compounds allows for subdivision into two classes of conformers with respect to the position of the benzhydryl group. This is confirmed by multiple regression analysis of the shift of the central benzhydryl proton, and by taking into consideration the shift difference between this proton and the one in the correspondingly substituted diphenylmethanol.

Author(s): M.L. de Winter und W.T. Nauta
Title: Pharmacochemistry of 2-diarylmethyl-1,3-indandiones. III. Conformational calculations
Eur. J. Med. Chem. Vol. 12, No. 2, p. 137-141 (1977); ISSN: 0223-5234; CODEN: EJMCA5


Abstract:
The division of a series of substituted 2-diarylmethyl-1,3-indandiones into two classes of conformers is substantiated by semiempirical calculations, covering only van-der-Waals interactions between non-bonded atoms. While the absolute energy values calculated for the various energy minima are not in accordance with the conformer behaviour observed, the dlfference between the compounds provides a qualitative confirmation. The structure calculated for the conformer constellations in the energy minima, were in agreement with the NMR data, as appeared from shift calculations.

Author(s): M.L. de Winter und W.T. Nauta
Title: Pharmacochemistry of 2-diarylmethyl-1,3-indandiones. IV. Anticoagulant activity in vivo.
Eur. J. Med. Chem. Vol. 12, No. 2, p. 141-145 (1977); ISSN: 0223-5234; CODEN: EJMCA5


Abstract:
A number of substituted 2-benzhydryl-1,3-indendiones and some related compounds were tested for anticoagulant activity. Equipotent doses were calculated in a regression analysis of the reciprocal percentage coagulant activity with log dose. Structure-activity relationships enabled to predict the inactivity of some ortho-substituted compounds in anti-conformation. The effect of para-substitution was compared with the activity of para-substitued 2-aryl-1,3-indandiones.

Author(s): M.L. de Winter und W.T. Nauta
Title: Pharmacochemistry of 2-diarylmethyl-1,3-indandiones. V. Anticoagulant activity in vitro
Eur. J. Med. Chem. Vol. 12, No. 2, p. 146-148 (1977); ISSN: 0223-5234; CODEN: EJMCA5


Abstract:
Warfarin and some 2-diarylmethyl-1,3-indandiones are shown to antagonize phylloquinone, measured by the production of coagulation factor VlI in vitro, using liver slices from vitamin K deficient rats. Dose-response curves of phylloquinone undergo a parallel shift to the right in the presence of the antagonists.

Author(s): L.E. Neilands und G. Vanags
Title: 2-Phenyl-4-azabenzo[f]-1,3-indandione, a new representative of heterocyclic compounds which are analogs of 1,3-indandione
Dokl. Chem. (Engl. Transl.) Vol. 146, No. 1-6, p. 841-843 (1962); ISSN: 0012-5008; CODEN: DKCHAY
Dokl. Akad. Nauk. SSR, Ser. Khim. Vol. 146, No. 3, p. 615-617 (1962); ISSN: 0002-3264; CODEN: DASKAJ

Author(s): L.E. Neilands und G. Vanags
Title: Ultraviolet spectra of 2-phenyl-4- and 2-phenyl-5-aza-1,3-indandiones
Chem. Heterocyclic Comp. Vol. 1, No. 1, p. 62-65 (1965); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 1, No. 1, p. 93-98 (1965); ISSN: 0132-6244; CODEN: KGSSAQ

Author(s): L.E. Neilands und G. Vanags
Title: Synthesis of some 2-aryl-5-aza-1,3-indandiones
Chem. Heterocyclic Comp. Vol. 1, No. 6, p. 597-599 (1965); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 1, No. 6, p. 879-883 (1965); ISSN: 0132-6244; CODEN: KGSSAQ

Author(s): L.E. Neilands und G. Vanags
Title: 2-(p-Nitrophenyl)-and 2-(p-Dimethylaminophenyl)-4-aza-5,6-benz-1,3-indandiones
Chem. Heterocyclic Comp. Vol. 1, No. 6, p. 600-602 (1965); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 1, No. 6, p. 884-888 (1965); ISSN: 0132-6244; CODEN: KGSSAQ

Author(s): I.V. Turovskii, Y.Y. Lindberg und O.Y. Neiland
Title: Structure of Aza-1,3-indandiones in solution
Chem. Heterocyclic Comp. Vol. 3, No. 1, p. 112-113 (1967); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 3, No. 1, p. 158-160 (1967); ISSN: 0132-6244; CODEN: KGSSAQ

Author(s): L.E. Neilands und G. Vanags
Title: 2-Aryl-4-aza-1,3-indandiones
Chem. Heterocyclic Comp. Vol. 3, No. 1, p. 81-83 (1967); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 3, No. 1, p. 114-118 (1967); ISSN: 0132-6244; CODEN: KGSSAQ

Author(s): L.E. Neilands
Title: Synthesis of 2-aryl-4-aza-1,3-indandiones and 2-aryl-4-aza-5,6-benz-1,3-indandiones
Chem. Heterocyclic Comp. Vol. 6, No. 5, p. 597-600 (1970); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 6, No. 5, p. 647-650 (1970); ISSN: 0132-6244; CODEN: KGSSAQ

Author(s): I.V. Turovskii, O.Y. Neiland, L.E. Neiland und Y.P. Stradyn'
Title: Electronic absorption spectra and protolysis of 4-aza- and 5-aza-1,3-indandiones
Chem. Heterocyclic Comp. Vol. 8, No. 10, p. 1249-1252 (1972); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 8, No. 10, p. 1382-1386 (1972); ISSN: 0132-6244; CODEN: KGSSAQ

Author(s): A.Y. Ozola, É.I. Stankevich und G.Y. Dubur
Title: A new method of sf synthesizing 4-aza-1,3-indandione derivatives
Chem. Heterocyclic Comp. Vol. 9, No. 8, p. 1062 (1973); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 9, No. 8, p. 1147-1148 (1973); ISSN: 0132-6244; CODEN: KGSSAQ

Author(s): O.Y. Neiland, S.V. Kalnin', É.I. Stankevich und A.Y. Ozola
Title: 4-Aza-1,3-indandione derivatives, I. Study of the tautomeric and prototropic equilibra of some analogs of 4-aza-1,3-indandiones
Chem. Heterocyclic Comp. Vol. 10, No. 4, p. 457-459 (1974); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 10, No. 4, p. 527-529 (1974); ISSN: 0132-6244; CODEN: KGSSAQ

Author(s): É.I. Stankevich, A.Y. Ozola und G.Y. Dubur
Title: 4-Aza-1,3-indandione derivatives, II. Synthesis of Tetrahydro-4-azabenz[f]indane-1,3,8-triones
Chem. Heterocyclic Comp. Vol. 11, No. 2, p. 199-202 (1975); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 11, No. 2, p. 231-234 (1975); ISSN: 0132-6244; CODEN: KGSSAQ

Author(s): A.Y. Ozola, É.I. Stankevich, S.V. Kalnin' und O.Y. Neiland
Title: 4-Aza-1,3-indandione derivatives, III. Reactivities and prototropic transformations of new 4-aza-1,3-indandiones
Chem. Heterocyclic Comp. Vol. 12, No. 2, p. 220-226 (1976); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 12, No. 2, p. 256-262 (1976); ISSN: 0132-6244; CODEN: KGSSAQ

Author(s): O.Y. Neiland und Y.Y. Katsen
Title: Phthalones and their structural analogs (review)
Chem. Heterocyclic Comp. Vol. 11, No. 4, p. 381-395 (1975); ISSN: 0009-3122; CODEN: CHCCAL
Khim. Geterotsikl. Soedin. Vol. 11, No. 4, p. 435-451 (1975); ISSN: 0132-6244; CODEN: KGSSAQ

Author(s): L.E. Neilands, A. Karklins, V. Veiss und G. Vanags
Title: Coulometric titration of cyclic b-diketones. IV. Coulometric bromination of some 4-aza- and 5-aza-1,3-indandiones
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 1, p. 7-10 (1964); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): L.E. Neilands und G. Vanags
Title: Condensation of chinchomeronic acid with phenylacetic acid
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 2, p. 203-210 (1964); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): O. Neiland, B. Karele und M. Cirule
Title: Preparation of ammonium derivatives of 2-phenyl-1,3-indandione
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 4, p. 471-481 (1964); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): O. Neiland und J. Linabergs
Title: Tautomeric conversions and polychromy of 2-(p-aminophenyl)-1,3-indandiones
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 6, p. 691-700 (1964); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): O. Neiland und V. Kroge
Title: Causes of coloration of 2-aryl-1,3-indandiones
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 4, p. 483-489 (1964); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): O. Neiland und M. Cirule
Title: Some derivatives of 2-(p-aminophenyl)-1,3-indandione
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 1, p. 65-70 (1963); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): O. Neiland, E. Silins, L. Taure und I. Smite
Title: The kinetics of the tautomerization of 2-(p-nitrophenyl)-1,3-indandione in the solid state
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 1, p. 75-81 (1966); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): O. Neiland
Title: Effect of substituents in the phthaloyl ring on the p-electron structure of 1,3-indandiones
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 5, p. 605-613 (1973); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): G. Vanags und V.P. Oshkaia
Title: 4-Nitro-1,3-indandione
J. Gen. Chem. USSR Vol. 28, No. 6, p. 1570-1573 (1958); ISSN: 0022-1279; CODEN: JGCHA4
Zh. Obshch. Khim. Vol. 28, No. 6, p. 1520-1524 (1958); ISSN: 0044-460X; CODEN: ZOKHA4

Author(s): V. Oskaja und G. Vanags
Title: Condensation of phthalic anhydride with phenylacetic acid in a solution of triethylamine and acetic anhydride
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 3, p. 67-76 (1961); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): V. Oskaja und G. Vanags
Title: Condensation of nitrophthalic anhydride with phenylacetic acid in triethylamine and acetic anhydride solution
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 6, p. 57-64 (1961); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): R. Zagata, V. Zelmene und G. Vanags
Title: Improved method for obtaining bindone
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 6, p. 71-76 (1961); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): V. Oskaja und G. Vanags
Title: Condensation of phthalic anhydride with benzyl cyanide and methyl benzyl ketone in triethylamine and acetic anhydride solution
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 8, p. 45-52 (1961); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): V. Oskaja und G. Vanags
Title: Condensation of dicarboxylic acid anhydrides with compounds containing active methylene groups. II. Condensation of 3-nitrophthalic anhydride with ethyl acetoacetate and malonate
Uch. Zap. Latv. Univ. Vol. 57, p. 67-71 (1964); ISSN: 0372-512X; CODEN: UZLUA2

Author(s): V. Oskaja und G. Vanags
Title: Condensation phthalic anhydride with phenylacetamide in acetic anhydride and triethylamine solution
Uch. Zap. Latv. Univ. Vol. 57, p. 77-80 (1964); ISSN: 0372-512X; CODEN: UZLUA2

Author(s): I.V. Bulgarovskaya, V.M. Vozzhennikov und M.A. Tovmasyan
Title: Anisotrophy of single crystal optical properties and photoconductivity of 2-(p-dimethylamino)benzylidene-1,3-indandione and 2-[4'-(dimethylamino)phenylpropen-2-ylidene]-1,3-indandione
Mater. Sci. Vol. 10, No. 1-2, p. 35-38 (1984); ISSN: 0137-1399; CODEN: MSCJDS


Abstract:
Polarized reflectance spectra of 2-(p-dimethylamino)benzylidene-1,3-indandione (1) and 2-[4'-(dimethylamino)propen-2-ylidene]-1,3-indandione (2) in the region 360-600 nm and the photoconduction in the wide spectral range 300-700 nm are reported. The assignment of the parent molecular transitions are p-p* singlets which are long axis polarized. An additional peak at 560 nm in the reflectance spectrum of the (100) face of the a-crystal from of compound 1 is assigned as an intermolecular charge-transfer transition. According to the spectral dependence the 1st step in the photoconduction process in the region 400-700 nm is the excitation of singlet excitions.

Author(s): V.Y. Khodorkovskii und O. Neiland
Title: 1-(1,3-Dithiol-2-ylidene)-2-(1,3-indandion-2-ylidene)ethanes
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 2, p. 245-246 (1986); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): I.V. Bulgarovskaya, A.N. Sobolev, V:E. Zavodnik, V.Y. Khodorkovskii und O. Neiland
Title: Crystal structure of 2-[4,5-(ethylidenedithio)-1,3-sithiol-2-ylidene]-1,3-indandione and 2-[[4,5-(ethylendithio)-1,3-dithiol-2-ylidene]acetyl]-3-hydroxybenzo[b]thiophene
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 3, p. 349-354 (1988); ISSN: 0002-3248; CODEN: LZAKAM

Author(s): V. Khodorkovskii und O. Neiland
Title: Phthalylideneacetyl chloride. I. Synthesis and properties of 1,3-indandione-2-carboxylic acid morpholide
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 5, p. 603-605 (1985); ISSN: 0002-3248; CODEN: LZAKAM


Abstract:
Chlorination of phthalylideneacetic acid I (R = OH) with SOCl₂ gave the corresponding acid chloride, which was amidated by morpholine to give an ylidene intermediate which rearranged to give the 3-Hydroxy-2-(morpholine-4-carbonyl)-inden-1-one. Treatment of 3-Hydroxy-2-(morpholine-4-carbonyl)-inden-1-one with Cu(OAc)₂ gave a copper bis complex.

Author(s): V. Khodorkovskii, E.L. Dubrovska und O. Neiland
Title: Phthalylideneacetyl chloride. II. Synthesis of 4-phthalylidenyl substituted derivatives of 1,3-dithioles and 1,3-dithiolium salts
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 5, p. 606-611 (1985); ISSN: 0002-3248; CODEN: LZAKAM


Abstract:
Treatment of phthalylideneacetic acid chloride, with diazomethane gave 93 % 3-(3-diazo-2-oxo-propylidene)-3H-isobenzofuran-1-one, which was halogenated with hydrochloric or hydrobromic acid to give 92 % 3-(3-chloro-2-oxo-propylidene)-3H-isobenzofuran-1-one or 90-92 % 3-(3-Bromo-2-oxo-propylidene)-3H-isobenzofuran-1-one, respectively, followed by treatment with sodium N-dimethyl-dithiocarbamate to give 94 % N,N-Dimethyl-dithiocarbamic acid 2-oxo-3-(3-oxo-3H-isobenzofuran-1-ylidene)-propyl ester. The latter was cyclized by sulfuric acid or perchloric acid followed by treatment with H₂S to give 87 % 3-(2-thioxo-[1,3]dithiol-4-ylmethylene)-3H-isobenzofuran-1-one. Additional obtained were 82 % 3-(2-Ethylsulfanyl-[1,3]dithiol-4-ylmethylene)-3H-isobenzofuran-1-one and 34.5 % of the tetrathiafulvalene derivate 4,4'-Bis(3H-isobenzofuran-1-one-3-methylenyl)-[2,2']bi[[1,3]dithiolylidene].

Author(s): V. Khodorkovskii und O. Neiland
Title: Synthesis and chemical properties of 1,3-dithioles and 1,3-dithiolium salts
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 2, p. 131-158 (1982); ISSN: 0002-3248; CODEN: LZAKAM


Abstract:
A review with 310 references.

Author(s): V. Khodorkovskii und O. Neiland
Title: Synthesis of tetrathiafulvalenes and their selena and tellura analogs
Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser., No. 6, p. 645-660 (1985); ISSN: 0002-3248; CODEN: LZAKAM


Abstract:
A review through 1984 with 168 references.

Author(s): R.A. Aitken, K. Ali, N. de Elena und P. Lightfoot
Title: Synthesis and structure of highly polarised double-bond compounds derived from S-proline
Tetrahedron Lett. Vol. 41, p. 7965-7968 (2000); ISSN: 0040-4039; CODEN: TELEAY

keywords: iminium salts; enamino esters; thiazolidines; X-ray crystal structures
Abstract:
Reaction of the chiral iminium salt 3 with stabilised carbanions gives the compounds 4–9 containing a highly polarised double bond. The extent of this polarisation is determined by variable temperature ¹H-NMR studies, comparison of ¹³C-NMR chemical shifts and an X-ray structure determination.

Author(s): K. Tanaka und F. Toda
Title: A novel photochromism of biindenylidene in crystal form
J. Chem. Soc., Perkin Trans. 1, p. 873-874 (2000); ISSN: 0300-922X; CODEN: JCPRB4


Abstract:
The yellow crystals of trans-syn-3,3'-diaryl-2,2'-biindenylidene-1,1'-diones (2) turned to reddish purple crystals when exposed to sunlight, which showed EPR signals of triplet biradicals in the solid state.

Inventor(s): M. Kuroda, N. Sekine, N. Kotani, K. Okura und Y. Ueno
Title: New cyano compound, electrophotographic photoreceptor and electrophotographic apparatus
(Fuji Electric Imaging Device Corp., Ltd., Japan) Jpn. Kokai Tokkyo Koho JP 2005035901, (10.02.2005); Patent Class.: C07C 255/34
CODEN: JKXXAF

Abstract of JP2005035901:
PROBLEM TO BE SOLVED: To provide a compound having an excellent electron transport ability and useful as an electrophotographic photoreceptor, the positively charged type electrophotographic photoreceptor for copiers and printers with high sensitivity and an electrophotographic apparatus using the same. SOLUTION: A cyano compound has a structure represented by general formula (I) (wherein, R1 s and R2 s are each the same or different and denote each a 1-6C alkyl group which may have a substituent, a 1-6C alkoxy group which may have a substituent, an aryl group which may have a substituent, a 1-6C alkylamino group or a halogen atom or adjacent two R1 s or R2 s may mutually be bound to form a ring; and m and n denote each an integer of 0-5). The electrophotographic photoreceptor and electrophotographic apparatus use the cyano compound.

Author(s): H. Meyer
Title: Über neue Derivate des Anthrachinons (erste Mitteilung über Zweikernchinone)
Monatsh. Chem. Vol. 30, p. 165-177 (1909); ISSN: 0026-9247; CODEN: MOCMB7

keywords: Dianthrone

Author(s): I. Alkorta, C. Wentrup und J. Elguero
Title: A theoretical study of the origin of rotational barriers in push-pull ethylenes
Theochem. Vol. 585, p. 27-34 (2002); ISSN: 0166-1280; CODEN: THEODJ


Abstract:
Using the B3LYP/6-31G* ab initio method, we have studied the rotation about the C=C bonds in 15 push-pull ethylenes of the general formula (X,Y)C=C(CHO)₂ [X, Y=NH₂, NHCH₃, N(CH₃)₂, OCH₃, SCH₃] in the gas phase. Two stationary points (minimum and transition state) were located for all compounds. The geometry, dipole moments, natural bond orbital atomic charges, as well as the rotational barriers were examined. The torsion angle depends essentially on the presence or absence of intramolecular hydrogen bonds, and the barrier is a function of the torsion angle.

Author(s): P.V. Bernhardt, R. Koch, D.W.J. Moloney, M. Shtaiwi und C. Wentrup
Title: Twisting and planarization in push-pull ethylenes
J. Chem. Soc., Perkin Trans. 2, p. 515-523 (2002); ISSN: 0300-9580; CODEN: JCPKBH


Abstract:
As determined by X-ray crystallography, Meldrum's acid derivatives 8-19 feature dihedral angles around the central C=C double bonds between 3 and 83 °. Hydrogen bonds between substituenfs RHN and the carbonyl groups favour near-planarity. Sterically demanding substituents favour large dihedral angles and zwitterionic structures as in formula 20. AM1 calculations of the structures are in excellent agreement with the experimental X-ray data, provided a dielectric field is incorporated (e = 40). This can be ascribed to the highly polar (zwitterionic) nature of the molecules. It is further predicted that all these molecules, including those that are stabilised in a planar form by intramolecular hydrogen bonds, undergo rapid rotation about the central C=C bonds at room temperature. DFT calculations incorporating a dielectric field model (PCM) are in excellent agreement with the near-perpendicular arrangement of the alkene moiety in 19.

Author(s): K. Gleu und S. Nitzsche
Title: Methylierte und methoxylierte 9-Chloracridine, Acridone und N-Methylacridone
J. Prakt. Chem. Vol. 153, No. 8-9, p. 200-224 (1939); ISSN: 0021-8383; CODEN: JPCEAO


Abstract
1. Es werden tabellarische Zusammenstellungen der Monomethyl- und Monomethoxylderivate folgender Grundkörper gegeben: a) Diphenylamin-2-carbonsäure. b) 9-Chloracridin. c) Acridon. d) N-Methylacridon.

Entry no. 449
Author(s): Jan Sandström
Title: Strained Olefins
In: The Chemistry of Double-Bonded Functional Groups, Saul Patai und Series ed.: Zvi Rappoport (ed.), p. 1253-1280 (1997); John Wiley & Sons, Ltd.; ISBN: 0-471-95956-1

Entry no. 450
Author(s): Jan Sandström
Title: Static and dynamic stereochemistry of push-pull and strained ethylenes
In: Top. Stereochem., N.L. Allinger, E.L. Eliel und S.H. Wilen (ed.), Vol. 14, p. 83-181 (1983); John Wiley & Sons, Ltd.

Author(s): J. Fabian und R. Zahradník
Title: The search for highly colored organic compounds
Angew. Chem. Int. Ed. Engl. Vol. 28, No. 6, p. 677-694 (1989); ISSN: 0570-0833; CODEN: ACIEAY
Angew. Chem. Vol. 101, No. 6, p. 693- (1989); ISSN: 0044-8249; CODEN: ANCEAD
keywords: color; conjugation; dyes; pigments; chromophores; theoretical chemistry
Abstract:
Until now the study of organic compounds in which the p-electron system is excited by absorbed light has been mainly concentrated on the ultraviolet and visible regions of the electromagnetic spectrum. Various new applications, such as the use of conjugated organic compounds as dye lasers or as materitals for storing information with the help of diode lasers, led to the synthesis of new compounds which absorb light in the near in infrared (NIR). It is possible to use structure-color relationships to predict the properties of such new compounds when they belong to dyestuff classes which have already been studied in detail; in this case the approach involves decreasing the energy difference between the ground state and the first excited state. A less conventional starting point is provided by molecular structures in which from the outset there is only a very small energy difference between the lowest-energy electronic states; such diradicaloid molecules occupy a special position among the various types of organic compounds. It is possible by means of suitable structural modification to stabilize such molecules in a singlet from which absorbs light at very long wavelengths (i.e. at small wave numbers).

Author(s): M.T. Zimaity und R. Afsah
Title: Some reactions with pyrindine-5,7(6H)-dione derivatives. Reactions of 6-carboethoxy-5H-1-pyrindine-5,7(6H)dione
Egypt. J. Chem. Vol. 21, No. 3, p. 217-228 (1978); ISSN: 0367-0422; CODEN: EGJCA3

keywords: 4-aza-1,3-indandione
Abstract:
The reaction of 6-carbethoxy-(5H)-1-pyrindine-5,7(6H)-dione (I) with hydrazine, phenylhydrazine, hydroxylamine and aromatic amines gave the corresponding dihydropyrazolo, isoxazolo and arylimino derivatives. The coupling of aryl diazonium salts with I gave (5H)-1-pyrindine-5,6,7-trione-6-aryl hydrazone (XVI). The arylidenes XVIII were prepared by reacting I with aryl aldehydes in alkaline medium. Their reaction with hydrazines and ethyl cyano acetate was investigated.

Author(s): G. Fischer und E. Kleinpeter
Title: Application of 2D EXSY NMR spectroscopy to the sudy of the dynamic behaviour of Aroyl cyano ketene-S,S-dimethyl acetals
Magn. Reson. Chem. Vol. 29, No. 3, p. 204-206 (1991); ISSN: 0749-1581; CODEN: MRCHEG


Abstract:
The applicability of 2D EXSY NMR spectroscopy for studying quantitatively the dynamic behaviour in three aroylcyanoketene-S,S-dimethylacetals was tested by means of ¹H-NMR spectroscopy. It can be concluded that the method is a reasonable quantitative supplement of complete line-shape analysis.

Author(s): S. Lalitha und A. Haug
Title: Spectroscopy of the lowest phosphorescent state of thiopyronine
J. Am. Chem. Soc. Vol. 93, No. 14, p. 3340-3342 (1971); ISSN: 0002-7863; CODEN: JACSAT

keywords: thiopyronine; triplet state
Abstract:
EPR and optical studies of randomly distributed molecules of thiopyronine photoexcited into the triplet state have been carried out at 77 °K. The zero-field-splitting parameter D* and the phosphorescence lifetime of the lowest triplet state decrease as the concentration is increased from 10(-6) to 10(-2) M. The decrease of this D* value is discussed in terms of intramolecular charge transfer and the delocalization of the triplet electrons over adjacent molecules.

Author(s): S.-S. Sun, C. Zhang, Z. Yang und L.R. Dalton
Title: Synthesis of 1,3-bis(dicyanomethylene)indane (BDMI) derived second order nonlinear optical polymers
Polym. Mater. Sci. Eng. Vol. 75, p. 225-226 (1996); ISSN: 0743-0515; CODEN: PMSEDG


Abstract:
Aminophenylenethienylidene-1,3-bisdicyanomethyleneindane (APT-BDMI)-based high-mb second-order nonlinear optical chromophores were covalently incorporated into polymer matrixes, such as polyester, polyurethane, and PMMA. Properties of these polymers are discussed.

Author(s): S. Nishiyama-Watanabe
Title: Photodynamic action of thiopyronine on the respiration and fermentation in yeast
Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. Vol. 30, No. 6, p. 501-509 (1976); ISSN: 0020-7616; CODEN: IJRBA3


Abstract
The efficiency of photodynamic treatment with thiopyronine (TP) on the respiration and fermentation of yeast cells, on the metabolic oxygen uptake of isolated mitochondrial preparations from yeast, and on the enzyme activity of alcohol dehydrogenase (ADH) in vivo and in vitro were studied. Respiration was inactivated by treatment with TP and visible light more at the initial stage than was the fermentation. Isolated mitochondria and ADH in vitro were not as sensitive to treatment as were respiration and fermentation in vivo. Inactivation patterns of respiration and fermentation in vivo showed that the inactivation was not due to damage to the DNA. The hindrance of respiration and fermentation might be one of main causes of cell-death resulting from photodynamic treatment.

Entry no. 457
Author(s): S.-S. Sun, C. Zhang, Z. Yang und L.R. Dalton
Title: Synthesis of 1,3-bis(dicyanomethylene)indane (BDMI) derived second order nonlinear optical polymers
In: Book of Abstracts, 212th ACS National Meeting, p. PMSE-151 (1996); American Chemical Society, Washington, D.C.; CODEN: 63BFAF; 212th ACS National Meeting, Orlando, FL, August 25-29, 1996

Abstract:
The amino-phenylenethienylidene-1,3-bis(dicyanomethylene)indane (APT-BDMI) based high mb push-pull 2nd order nonlinear optical chromophores have been covalently incorporated into polymer matrixes. Optical quality thin films can be obtained via spin coating. Three types of BDMI polymers have been explored, including polyesters, polyurethanes and polymethylmethacrylate. Since the strong electron acceptor BDMI is sensitive to some polymn. reaction conditions, we therefore pursue polymn. of the APT-aldehyde pre-chromophores first, then couple the BDMI to the aldehydic polymer. This synthetic scheme has been shown to work since the aldehyde group were found intact during our polymn. reactions. The synthetic route may also be applicable for other strong electron acceptors that are coupled to the donor-bridge systems via aldehyde group for fabrication of electro-optical polymers.

Author(s): P.M. Borsenberger, E.H. Magin, M. van der Auweraer und F.C. de Schryver
Title: Electron transport in vapor-deposited layers of 2-methyl-2-pentyl-1,3-bis(dicyanomethylene)indane
Phys. Stat. Solidi B Vol. 186, No. 1, p. 217-224 (1994); ISSN: 0370-1972; CODEN: PSSBBD


Abstract:
Electron mobilities were measured in vapor-deposited amorphous layers of 2-methyl-2-pentyl-1,3-bis(dicyanomethylene)indane, a highly polar acceptor compound with a dipole moment of 3.9 D. The results are described within the framework of a formalism based on disorder, due to H. Baessler and coworkers. The parameters of the formalism are s, the variance of the hopping site energies, m0, a prefactor mobility, and S, the degree of positional disorder. Experimental values of s, m0, and S are 0.112 eV, 1.6 x 10(-3) cm²/V-s, and 1.6. The variance of site energies can be described by a model based on dipolar disorder. A comparison of the prefactor mobility with literature values for vapor-deposited acceptor glasses suggests that the prefactor is dependent on dipole moment, decreasing with increasing moment. The degree of positional disorder is similar to that obsd. in a wide range of vapor-deposited mol. glasses and attributed to packing constraints.

Author(s): P.V. Pastors
Title: Condensation of b-dicarbonyl compounds with malononitrile
Biol. Akt. Savienojumu Khim. Tekhnol. Rigas Politekh. Inst. (Khim. Tekhnol. Biol. Akt. Soed.) Vol. 1, p. 75-80 (1964-1973 (1974)); CODEN: BASIDS


Abstract:
Cyclocondensation of CH₂(CN)₂ with CH₂(Ac)₂ and CH₂(Bz)₂ gave 3-cyano-4,6-dimethyl-2(1H)-pyridinone and 3-cyano-4,6-diphenyl-2(1H)-pyridinone, respectively. The cyclohexanones I (R, R1 = H, Me, Ph, furyl) were prepared by condensation of CH₂(CN)₂ with 5-substituted 1,3-cyclohexanediones; I underwent acylation, alkylation, mono- and dihalogenation reactions at C-2. The quinolinediones II (R2 = Ph, furyl) were obtained by cyclocondensation of appropriate 2-acetyl-1,3-cyclohexanediones with CH₂(CN)₂, and the isoquinolinediones III (R3, R4 = H, Me; R5 = Ph, Me) by treatment of 2-(aminomethylene)-1,3-cyclohexanediones with CH₂(CN)₂. Condensation of 1,3-indandione with CH₂(CN)₂ gave 1,3-bis(dicyanomethylene)indan (IV) which reacted with benzaldehydes to give 2-benzylidene derivatives of IV.

Author(s): L.A. Chetkina, V.K. Bel'skii, E.G. Popova, B.P. Bespalov und A.G. Abolin
Title: The structure of the monoclinic modification of 1,3-bis(dicyanomethylene)-2-(4'-(N,N-diethylamino)phenylimino)indane
Zh. Strukt. Khim. Vol. 31, No. 3, p. 163-165 (1990); ISSN: 0044-4634; CODEN: ZSTKAI
J. Struct. Chem. (USSR) (Engl. Transl.) Vol. 31, No. 3 (1990); ISSN: 0022-4766; CODEN: JSTCAM

Abstract:
The atom coordinates are given. The structure was solved by direct methods and refined by least-squares to R = 0.032. The bond lengths and angles are given.

Author(s): M.R. Detty, P.N. Prasad, D.J. Donnelly, T. Ohulchanskyy, S.L. Gibson und R. Hil
Title: Synthesis, properties, and photodynamic properties in vitro of heavy-chalcogen analogues of tetramethylrosamine
Bioorg. Med. Chem. Vol. 12, No. 10, p. 2537-2544 (2004); ISSN: 0968-0896; CODEN: BMECEP

keywords: thiopyronine; alternative synthesis of 3,6-Bis(dimethylamino)-selenoxanthone; 3,6-Bis(dimethylamino)-thioxanthone
Abstract:
Thio and seleno analogues of tetramethylrosamine were prepared by the directed-metalation/cyclization of the corresponding N,N-diethyl 2-(3-dimethylaminophenylchalcogeno)-4-dimethylaminobenzamide to the 2,7-bis-(N,N-dimethylamino)-9H-chalcogenoxanthen-9-one followed by the addition of phenylmagnesium bromide, dehydration, and ion exchange to the chloride salt. The thio and seleno tetramethylrosamines had longer wavelengths of absorption and higher quantum yields for the generation of singlet oxygen than tetramethylrosamine. Both the thio and selenoanalogues of tetramethylrosamine were e.cient photosensitizers against R3230AC rat mammary adenocarcinoma cells in vitro. l_max for tetramethyrosaminea and the thio- and seleno-analogues are tabulated.

Author(s): K. Gleu und S. Nitzsche
Title: Methylierte und methoxylierte N-Methylthioacridone und N-Methylacridonanile
J. Prakt. Chem. Vol. 153, No. 8-9, p. 225-232 (1939); ISSN: 0021-8383; CODEN: JPCEAO

Author(s): K. Gleu und S. Nitzsche
Title: Methylierte und methoxylierte N,N'-Dimethyldiacridine und N,N'-Dimethyldiacridylium-salze
J. Prakt. Chem. Vol. 153, No. 8-9, p. 233-241 (1939); ISSN: 0021-8383; CODEN: JPCEAO

Entry no. 464
Author(s): Wassil Topalow
Title: Über die Thiopyronine. Ein Beitrag zur Konstitution der Rhodole
(1903); Univ. Diss., Basel

Author(s): H. Berg, F.A. Gollmick, H.E. Jacob und H. Triebel
Title: Sensitized photooxidation through methylene blue, thiopyronine, and pyronine. II. Physicochemical bases for the photodynamic effectiveness of thiopyronine
Photochem. Photobiol. Vol. 16, No. 2, p. 125-138 (1972); ISSN: 0031-8655; CODEN: PHCBAP

Author(s): H. Berg, F.A. Gollmick, H.E. Jacob und H. Triebel
Title: Methylene blue thiopyronin and pyronin-sensitized photooxidation. III. Mechanism of photosensitized oxidation of guanosines by thiopyronin
Photochem. Photobiol. Vol. 16, No. 5, p. 447-453 (1972); ISSN: 0031-8655; CODEN: PHCBAP

Author(s): W. Müller und D.M. Crothers
Title: Interactions of heteroaromatic compounds with nucleic acids - 1. The influence of heteroatoms and polarizability on the base specificity of intercalating ligands
Eur. J. Biochem. Vol. 54, No. 1, p. 267-277 (1975); ISSN: 0014-2956; CODEN: EJBCAI

keywords: 3,6-Bis(dimethylamino)thioxanthylium perchlorate; thiopyronine perchlorate
Abstract:
We have examined the origins of base specificity in intercalating ligands by studying the interaction with DNA of a series of proflavine and acridine orange analogs differing in the heteroatoms present in the chromophore. Base specificity was determined by differential dialysis of the dye against DNA samples of differing G · C content. We find that G · C specificity increases as the visible absorbance band of the chromophore moves to longer wavelength, implying a relation between specificity and polarizability of the chromophore. This can be rationalized by recognizing that the G · C pair is more polar than A · T, and should therefore interact more favorably with an easily polarized ring system. We find in addition that dimethylation of the chromophore amino groups increases specificity which we discuss in terms of steric and coupled steric-electronic contributions. Our results also bear on the origin of G · C specificity in binding actinomycin to DNA. Some of the compounds studied are as G · C specific as actinomycin, yet they lack hydrogen-bonding functions as plausible determinants of specificity. This observation gives new life to the hypothesis that the specificity of actinomycin is determined primarily by preferential interaction of the chromophore with a G · C pair.

Author(s): W. Müller, H. Bunemann und N. Dattagupta
Title: Interactions of heteroaromatic compounds with nucleic acids - 2. Influence of substituents on the base and sequence specificity of intercalating ligands
Eur. J. Biochem. Vol. 54, No. 1, p. 279-291 (1975); ISSN: 0014-2956; CODEN: EJBCAI


Abstract:
This paper presents the results of a systematic study on the effects of substituents on the base and sequence specificity of tricyclic heteroaromatic compounds interacting with DNA by intercalation. All the compounds tested are derived from proflavine and acridine orange analogs with different heteroatoms in the middle ring. Their base and sequence specificities were determined by differential dialysis of the ligand against DNA samples of differing G-C content. The main results indicate that (a) the introduction of a phenyl substituent into one of the two available positions of the middle ring increases or decreases the G-C specificity of the ligand depending on the position where the substitution takes place; (b) compounds of the substitution type of neutral red (2-methyl-3-amino-7-dimethyl-amino-phenazine) show unexpectedly high G-C specificities and (c) DNA ligands of pronounced sequence specificity for adjacent G-C pairs can be constructed by combining the structural elements of neutral red with an additional phenyl residue in the same molecule. The further study of compounds related to the phenylated neutral red revealed that the G-C specificity can be improved or destroyed by additional substituents. The comparison of the G-C specificity and the DNA-affinity data of the compounds studied leads to the suggestion that the specificity arises mainly from electronic factors which are strongly controlled through steric constraints on possible ocmplex geometries. As a basis for the discussion a possible structure for the DNA complex of the phenylated neutral red is considered in which the extra phenyl ring at N-5 of the phenazinium system, protrudes into the large groove of the DNA helix while the tricyclic part of the ligand is inserted between the DNA base-pairs.

Author(s): W. Müller und F. Gautier
Title: Interactions of heteroaromatic compounds with nucleic acids - 3. A - T-specific non-intercalating DNA ligands
Eur. J. Biochem. Vol. 54, No. 2, p. 385-394 (1975); ISSN: 0014-2956; CODEN: EJBCAI


Abstract:
In the present paper we report the results of a study on the base specificity and affinity of eight dyes potentially able to interact with DNA. These compounds include four triphenylmethane dyes used in histochemistry, auramine, "Hoechst 33258" and two acridines substituted with t-butyl groups. They were selected with regard to their inability to intercalate between the base pairs of helical polynucleotides due to structural limitations. Hydrodynamic studies performed with the DNA complexes of crystal violet and Hoechst 33258 confirmed our assumptions that compounds of this type bind to the outside of DNA. The main results from DNA binding studies indicate that the triphenylmethane dyes except p-fuchsin are bound with high preference to two adjacent A - T pairs while Hoechst 33258 seems to need three A - T pairs as the binding site. Model studies with synthetic polynucleotides revealed that not only a sequence of A - T pairs, but also their structural arrangement in a helix, is crucial for the high affinities observed for most of the ligands when interacting with natural DNA. Methyl green and Hoechst 33258 can be used for increasing the resolution power of cesium chloride density gradients for DNAs with different (A + T) content.