Effect of molecular structure and hydrogen bonding on the fluorescence of hydroxy-substituted naphthalimides

Physical Chemistry Chemical Physics

Volumn 1, Issue 20, 1999, Pages 4759-4766

  Biczók, László ^a   Valat, Pierre ^b   Wintgens, Véronique ^b  

^a CHEMICAL RESEARCH CENTER   (Hungary)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; BINDING AFFINITY; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; FLUORESCENCE; HYDROGEN BOND;

EID: 0033569522     PISSN: 14639076     EISSN: None     Source Type: Journal    
DOI: 10.1039/a904520a     Document Type: Article

References (40)

1. J. Herbich, C.-Y. Hung, R. P. Thummel and J. Waluk, J. Am. Chem. Soc., 1996, 118, 3508 and references therein.
2. H. Inoue, M. Hida, N. Nakashima and K. Yoshihara, J. Phys. Chem., 1982, 86, 3184.
3. R. S. Moog, N. A. Burozski, M. M. Desai, W. R. Good, C. D. Silvers, P. A. Thompson and J. D. Simon, J. Phys. Chem., 1991, 95, 8466; J. Ritter, H. U. Borst, T. Lindner, M. Hauser, S. Brosig, K. Bredereck, U. E. Steiner, D. Kühn, J. Kelemen and H. E. A. Kramer, J. Photochem. Photobiol A, 1988, 41, 227; H. U. Borst, J. Kelemen, J. Fabian, M. Nepras and H. E. A. Kramer, J. Photochem. Photobiol. A, 1992, 69, 97.
4. R. S. Moog, N. A. Burozski, M. M. Desai, W. R. Good, C. D. Silvers, P. A. Thompson and J. D. Simon, J. Phys. Chem., 1991, 95, 8466; J. Ritter, H. U. Borst, T. Lindner, M. Hauser, S. Brosig, K. Bredereck, U. E. Steiner, D. Kühn, J. Kelemen and H. E. A. Kramer, J. Photochem. Photobiol A, 1988, 41, 227; H. U. Borst, J. Kelemen, J. Fabian, M. Nepras and H. E. A. Kramer, J. Photochem. Photobiol. A, 1992, 69, 97.
5. R. S. Moog, N. A. Burozski, M. M. Desai, W. R. Good, C. D. Silvers, P. A. Thompson and J. D. Simon, J. Phys. Chem., 1991, 95, 8466; J. Ritter, H. U. Borst, T. Lindner, M. Hauser, S. Brosig, K. Bredereck, U. E. Steiner, D. Kühn, J. Kelemen and H. E. A. Kramer, J. Photochem. Photobiol A, 1988, 41, 227; H. U. Borst, J. Kelemen, J. Fabian, M. Nepras and H. E. A. Kramer, J. Photochem. Photobiol. A, 1992, 69, 97.
6. L. Biczók, T. Bérces and H. Linschitz, J. Am. Chem. Soc., 1997, 119, 11071.
7. T. Yatsuhashi and H. Inoue, J. Phys. Chem. A, 1997, 101, 8166.
8. T. Yatsuhashi, Y. Nakajima, T. Shimada, H. Tachibana and H. Inoue, J. Phys. Chem. A, 1998, 102, 8657.
9. C. Turró, C. K. Chang, G. E. Leroi, R. I. Cukier and D. G. Nocera, J. Am. Chem. Soc., 1992, 114, 4013.
10. R. I. Cukier and D. G. Nocera, Annu. Rev. Phys. Chem., 1998, 49, 337.
11. W. J. Liegh, E. C. Lathioor and M. J. St Pierre, J. Am. Chem. Soc., 1996, 118, 12339.
12. N. Mataga and H. Miyasaka, Prog. React. Kinet., 1994, 19, 317 and references therein.
13. H. Miyasaka, K. Wada, S. Ojima and N. Malaga, Isr. J. Chem., 1993, 33, 183.
14. V. Wintgens, P. Valat, J. Kossanyi, A. Demeter, L. Biczók and T. Bérces, New J. Chem., 1996, 20, 1149.
15. L. M. Tolbert and J. E. Haubrich, J. Am. Chem. Soc., 1990, 112, 8163.
16. L. M. Tolbert and J. E. Haubrich, J. Am. Chem. Soc., 1994, 116, 10593.
17. D. Huppert, L. M. Tolbert and S. Linares-Samaniego, J. Phys. Chem. A, 1997, 101, 4602.
18. V. Wintgens, P. Valat, J. Kossanyi, L. Biczók, A. Demeter and T. Bérces, J. Chem. Soc., Faraday Trans., 1994, 90, 411.
19. W. Adam, X. Quian and C. R. Saha-Möller, Tetrahedron, 1993, 49, 417.
20. R. Royer, J. P. Buisson, P. Demerseman and J. P. Lechartier, Bull. Soc. Chim. Fr., 1969, 2792.
21. W. M. Rodionow and A. M. Fedorowa, Bull. Soc. Chim. Fr., 1939, 479.
22. P. Valat, V. Wintgens, J. Kossanyi, L. Biczók, A. Demeter and T. Bérces, J. Am. Chem. Soc., 1992, 114, 947.
23. S. L. Murov, G. L. Carmichael and I. Hug, Handbook of Photochemistry, Marcel Dekker, New York, 2nd edn., 1993.
24. J. K. Hurley, N. Sinai and H. Linschitz, Photochem. Photobiol, 1983, 38, 9.
25. T. Förster, Z. Electrochem., 1950, 54, 531.
26. The HyperChem program package was used. The geometry of the molecule was optimized by AM1 calculation and the energy levels were obtained by ZINDO/S method.
27. A. Prado, J. Campanario, J. M. L. Poyato, J. J. Camacho, D. Reyman, E. Martin, THEOCHEM., 1988, 166, 463.
28. N. Malaga and S. Tsuno, Bull. Chem. Soc. Jpn., 1957, 30, 368.
29. J. R. Lakowicz, Principles of fluorescence spectroscopy, Plenum Press, New York, 1983, p. 266.
30. D. V. O'Connor, L. Chewter and D. Phillips, J. Phys. Chem., 1982, 86, 3400.
31. E. Fischer, Ber. Bunsen-Ges. Phys. Chem., 1969, 73, 1007.
32. L. Biczók, T. Bérces and H. Inoue, J. Phys. Chem. A., 1999, 103, 3837.
33. M. Adachi, Y. Murata and S. Nakamura, J. Phys. Chem., 1995, 99, 14240.
34. E. P. L. Hunter and S. G. Lias, J. Phys. Chem., Ref. Data, 1998, 27, 707.
35. C. W. Bird, Tetrahedron, 1985, 41, 1409; ibid., Tetrahedron, 1986, 42, 89.
36. C. W. Bird, Tetrahedron, 1985, 41, 1409; ibid., Tetrahedron, 1986, 42, 89.
37. A. R. Katritzky, M. Karelson and N. Malhotra, Heterocycles, 1991, 32, 127.
38. D. Gurka and R. W. Taft, J. Am. Chem. Soc., 1969, 91, 4794.
39. R. W. Taft, D. Gurka, L. Joris, P. von R. Schleyer and J. W. Rakshys, J. Am. Chem. Soc., 1969, 91, 4801.
40. M. H. Abraham, P. P. Duce, D. V. Prior, D. G. Barrett, J. J. Morris and P. J. Taylor, J. Chem. Soc., Perkin Trans. 2, 1989, 1355.