Quantum chemical calculations, synthesis, and properties of novel organic molecules with photo-induced intramolecular electron transfer and giant change of the electric dipole moment in the exited state

Proceedings of SPIE - The International Society for Optical Engineering

Volumn 2968, Issue , 1997, Pages 13-18

  Neilands, Ojars ^a   Utinans, Maris ^a  

^a RIGA TECHNICAL UNIVERSITY   (Latvia)

Author keywords

1,3 indandione anion; Betaines; Diazole anions; Dipole moments; Electron absorption spectra; Localized molecular orbitals; N pyridinium cation; Nonlinear optical effects; Photoinduced intramolecular electron transfer; Quantum chemical calculations

Indexed keywords

ABSORPTION; AROMATIC COMPOUNDS; AUGER ELECTRON SPECTROSCOPY; CHEMICAL BONDS; CHEMICAL COMPOUNDS; CHEMICAL PROPERTIES; COMPLEXATION; DIPOLE MOMENT; ELECTRIC CONDUCTIVITY; ELECTRIC DIPOLE MOMENTS; ELECTROMAGNETIC WAVE ABSORPTION; ELECTRON ABSORPTION; ELECTRON TRANSITIONS; ELECTRONS; ENERGY ABSORPTION; INTERCONNECTION NETWORKS; IONS; LIGHT ABSORPTION; MOLECULAR MODELING; MOLECULAR ORBITALS; MOLECULES; NEGATIVE IONS; NONLINEAR OPTICS; ORGANIC COMPOUNDS; POSITIVE IONS; QUANTUM CHEMISTRY; SEMICONDUCTING ORGANIC COMPOUNDS; SEMICONDUCTOR MATERIALS; SPECTRUM ANALYSIS; SYNTHESIS (CHEMICAL); TERNARY SYSTEMS;

1,3-INDANDIONE ANION; BETAINES; DIAZOLE ANIONS; ELECTRON ABSORPTION SPECTRA; LOCALIZED MOLECULAR ORBITALS; N-PYRIDINIUM CATION; NONLINEAR OPTICAL EFFECTS; PHOTOINDUCED INTRAMOLECULAR ELECTRON TRANSFER; QUANTUM CHEMICAL CALCULATIONS;

INTEGRATED OPTOELECTRONICS;

EID: 0040573115     PISSN: 0277786X     EISSN: None     Source Type: Conference Proceeding    
DOI: 10.1117/12.266818     Document Type: Conference Paper

References (15)

1. M.R. Wasielewski, "Photoinduced electron transfer in supramolecular systems for artificial photosynthesis",Chem.Rev. 92(3), 435-461(1992).
2. H.Kurreck, and M.Huber, "Model reactions for photosynthesis- photoinduced charge and electron transfer between covalently linked porphyrin and quinone units", Angew.Chem.Int.Ed.Engl. 34, 849-866.
3. J.Zyss, I.Ledoux, and J.-F.Nicoud," Advances in molecular engineering for quadratic nonlinear optics", Molecular Nonlinear Optics. Academic Press.Inc., 129-200(1994).
4. T.J.Marks, and M.A.Ratner,"Designe, synthesis, and properties of molecule-based assemblies with large second-order optical nonlinearities", Angew.Chem.Int.Ed.Eng. 34,156-173(1995).
5. J.F.Freimanis, "Organic compounds with intramolecular charge transfer", Zinatne, Riga, 1985. (in Russian)
6. H.S.Paley, and J.M.Harris, "Synthesis and characterisation of some pyridinium-N-phenoxide betaine dyes for second-harmonic generation", J.Org.Chem. 56(2), 568-574(1991).
7. K.J.Drost, V.Pushkara Rao, and A.K-Y.Jen,"A new synthetic approach for the incorporation of highly efficient second-order nonlinear optical chromophores containing tricyanovinyl electron acceptors into methacrilate polymers", J.Chem.Soc.Chem.Commun. 1994, 369-371.
8. P.Boldt, G.Bourhill, Ch.Brauchle, Y.Jim, R.Kammler, Ch. Muller, J.Rase, and J.Wichern,"Tricyanoquinodimethane derivatives with extremely large second-order optical nonlinearities",J.Chem.Soc.Chem.Commun. 1996,793-795.
9. O.Neiland,"The characterization of π-electron structure of active methylene group betaine like derivatives. 3. 2-N-pyridiniumindandione-1,3 betaine",Izv.AN Latvian SSR. Ser.Chim.1971(1), 85-91 (in Russian)
10. V.E.Kampar, Z.P.Bruvers, and O.Y.Neiland,"The calculation of electron spectra in CNDO/S approximation and character of long wave absorption band of 2-N-pyridinium-1,3-indandione betaine",Chem.Heterocycl. Componds.1981(5), 658-661.
11. M.A.Rutkis, L.E.Gerca, E.A.Silinsh, O.Y.Neilands, M.P.Roze, E.L.Berzinsh,.A.B.Klimkans, and S.Larsson"Langmuir-Blodgett films of indandione-1,3 pyridinium betaine. I:Preparation, electronic structure. optical properties",Adv.Mater.Opt.Electr.1993(2),319-330.
12. G.Liberts, V.Zauls, and O.Neilands,"Nonlinear optical properties of some indandione-1,3 betaine derivatives", these SPIE Proceedings
13. E.Alcalde, I.Dinares, J.-P.Fayet, M.-C.Vertut, and J.Elguero, "Synthesis of highly dipolar betaines: pyridinium azolates", J.Chem.Soc.Chem.Commun.1986,734-735.
14. D.M.Burland, R.Miller, and C.A.Walsh,"Second-order nonlinearity in poled-polymer systems", Chem.Rev. 94(1), 31-75(1994).
15. S. Yitzchaik, and T.J.Marks," Chromophoric self-assembled superlattices",Acc.Chem.Research. 29(4), 197-202(1996).