Dual luminescence properties of differently benzo-fused N-phenylphenanthridinones

Photochemical and Photobiological Sciences

Volumn 2, Issue 3, 2003, Pages 273-281

  Demeter, Attila ^a   Bérces, Tibor ^a   Hinderberger, Julia ^b,c   Timári, Géza ^b  

^a CHEMICAL RESEARCH CENTER   (Hungary)

^b Chinoin Pharmaceutical and Chemical Works Ltd   (Hungary)

^c UNIVERSITY OF FREIBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

6 NAPTHTHALEN 2 YL 6H BENZO[I]PHENANTHRIDIN 5 ONE; ALPHA NAPHTHYL; BENZO PHENANTHRIDINONE; BETA NAPHTHYL; KETONE DERIVATIVE; N PHENYLPHENANTHRIDINONE; NAPHTHYL GROUP; PHENANTHRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMOLUMINESCENCE; COMPLEX FORMATION; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 27844467725     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b210592f     Document Type: Article

References (30)

1. E. Lippert, W. Lüder and H. Boos, Fluoreszenzspektrum und Franck-Condon Prinzip in Lösungen aromatischer Verbindungen, in Advances in Molecular Spectroscopy: European Conference on Molecular Spectroscopy, Bologna, Italy, 1959, ed. by A. Mangini, Pergamon Press, Oxford. 1962, p. 443-457.
2. Y. V. Il'ichev, W. Kühnle and K. A. Zachariasse, Intramolecular charge transfer in dual fluorescent 4-(dimethylamino)benzonitriles. Reaction efficiency enhancement by increasing the size of the amino and benzonitrile subunits by alkyl substituents, J. Phys. Chem. A, 1998, 102, 5670-5680;
3. A. Demeter, S. Druzhinin, M. George, E. Hasselbach, J. L. Roulin and K. A. Zachariasse, Dual fluorescence and fast intramolecular charge transfer with 4-(diisopropylamino)benzonitrile in alkane solvents, Chem. Phys. Lett., 2000, 323, 351-360 and references therein.
4. A. Demeter, T. Bérces, L. Biczók, V. Wintgens, P. Valat and J. Kossanyi, Comprehensive model of the photophysics of N-phenylnaphthalimides: The role of solvent and rotational relaxation, J. Phys. Chem. A, 1996, 100, 2001-2011;
5. V. Wintgens, P. Valat, J. Kossanyi, L. Biczók, A. Demeter and T. Bérces, Spectroscopic properties of aromatic dicarboximides, J. Chem. Soc., Faraday Trans., 1994, 90, 411-421.
6. A. Demeter, G. Timári, A. Kotschy and T. Bérces, The influence of aryl substitution on the photophysics of 1-aryl-fluorenones, Tetrahedron Lett., 1997, 38, 5219-5222.
7. W. Rettig and M. Zander, Broken symmetry in excited states of 9,9′-bianthryl, Ber. Bunsenges. Phys. Chem., 1983, 87, 1143-1149;
8. G. Grabner, K. Rechthaler and G. Köhler, Two-state model for the photophysics of 9,9′-bianthryl. Fluorescence, transient-absorption, and semiempirical studies, J. Phys. Chem. A, 1998, 102, 689-696 and references therein.
9. A. Demeter, T. Bérces and K.A. Zachariasse, Dual fluorescence and intramolecular charge transfer with N-phenylphenanthridinones, J. Phys. Chem. A, 2001, 105, 4611-4621.
10. V. Wintgens, P. Valat, J. Kossanyi, A. Demeter, L. Biczók and T. Bérces, Spectroscopic properties of aromatic dicarboxiimides. Part 4. On the modification of the fluorescence and intersystem crossing processes of molecules by electron-donating methoxy groups at different position. The case of 1,8-naphthalimides, New J. Chem., 1996, 20, 1149-1158.
11. V. Simanek, Benzophenantridine Alkaloids, A. Brossi Ed.; The Alkaloids, Chemistry and Pharmacology, Academic, Orlando, 1985, Vol. 26, pp 209-224.
12. M. Cushman, P. Machan and E. C. R. Smith, Synthesis and biological-activity of structural analogs of the anticancer benzophenanthridine alkoloid nitidine chloride, J. Med. Chem., 1984, 27, 544-547.
13. V. Arisvaran, M. Ramesh, S. P. Rajendran and P. Shamugam, Synthesis of benzo[k]phenanthridines - another new approach, Synthesis, 1981, 821-823.
14. A. R. Katritzky, L. Xiangfu and J. N. Lam, Ring Fragmentation of benzotriazol-1-yl carbanions, Chem. Ber., 1991, 124, 1431-1434.
15. G. Timári, T. Soós and Gy. Hajós, A convenient synthesis of two new indoloquinoline alkaloids, Synlett, 1997, 1067-1068;
16. T. Soós, G. Timári and Gy. Hajós, A concise synthesis of furostifoline, Tetrahedron Lett., 1999, 40, 8607-8609;
17. M. Béres, G. Timári and Gy. Hajós, Straightforward synthesis of 11H-indolo[3,2-c]isoquinoline and benzofuro[3,2-c]isoquinoline by ring transformation, Tetrahedron Lett., 2002, 43, 6035-6038.
18. J. O. Osby and B. Ganem, Rapid and efficient reduction of aliphatic nitro compounds to amines, Tetrahedron. Lett., 1985, 26, 6413-6416.
19. E. C. Taylor and G. G. Spence, in Organic Photochemical Syntheses, Vol.1, Ed. R. Srinivasan, Wiley-Intersciences, New York, 1971, 89-92.
20. A. B. Shahripour, M. S. Plummer, E. A. Lunney, H. P. Albrecht, S. J. Hays, C. R. Kostlan, T. K. Sawyer, N. P. C. Walker, K. D. Brady, H. J. Allen, R. V. Talanian, W. W. Wong and C. Humblet, Structure-based design of nonpeptide inhibitors of interleukin-Iβ converting enzyme (ICE, Caspase-I), Bioorg. Med. Chem., 2002, 10, 31-40.
21. V. Kesavan and N. Arumugam, Lithium aluminium hydride reduction of 1-aryl-2-oximinocyclohexanes and 1-aryl-2-nitrocyclohexenes, Ind. J. Chem., 1968, 6, 694-695.
22. M. Mintas, V. Mihaljevic, H. Koller, D. Schuster and A. Mannschreck, Sterically hindered N-aryl-2(1H)-quinolones and N-aryl-6(5H)-phenanthridinones: separation of enantiomers and barriers to racemization, J. Chem. Soc., Perkin Trans. 2, 1990, 619-624;
23. R. J. Gillespie, Molecular Geometry Van Nostrand Reinhold CO., London 1972.
24. N. L. Weinberg and H. R. Weinberg, Electrochemical oxidation of organic compounds, Chem. Rev., 1968, 68, 449-523.
25. HyperChem, Hypercube, Inc.: Gainesville, Fl, 1994.
26. A. Streitwieser, Jr., Molecular Orbital Theory for Organic Chemists; John Wiley: New York, 1961.
27. B. Stevens and M. I. Ban, Spectrophotometric determination of enthalpies and entropies of photoassociation for dissolved aromatic hydrocarbons, Trans. Faraday Soc., 1964, 60, 1515-1523.
28. F. D. Rossini, K. S. Pitzer, R. L. Arnett, R. M. Braun and G. C. Pimentel, Selected Values of Physical and Thermodynamic Properties of Hydrocarbons and Related Compounds, 1953, Carnegie Press, 226-227.
29. E. Lippert, Dipolmoment und Elektronenstructur von angeregten Molekülen, Z. Naturforsch., 1955, 10A, 541-544.
30. N. Mataga, Y. Kaifu and M. Koizumi, Solvent effect upon fluorescence spectra and the dipole moments of excited molecules, Bull. Chem. Soc. Jpn., 1956, 29, 465-470.