Photoinduced intramolecular electron transfer between carbazole and bis(trichloromethyl)-s-triazine generating radicals

Journal of Physical Chemistry B

Volumn 107, Issue 19, 2003, Pages 4579-4586

  Kawamura, Koichi ^a   Aotani, Yoshimasa ^a,b   Tomioka, Hideo ^c  

^a FUJIFILM CORPORATION   (Japan)

^b MIE UNIVERSITY   (Japan)

^c Sankio Chemical Co Ltd   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CHLORINE COMPOUNDS; DYES; ELECTRON TRANSPORT PROPERTIES; INITIATORS (CHEMICAL); MIXTURES; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOPOLYMERIZATION; PHOTOSENSITIVITY; PLASTIC FILMS;

BISTRICHLOROMETHYL-S-TRIAZINE; CARBAZOLE; PHOTOINDUCED INTRAMOLECULAR ELECTRON TRANSFER; PHOTOINITIATOR; PHOTOPOLYMER FILM;

FREE RADICALS;

EID: 0038728343     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp027253u     Document Type: Article

References (49)

1. (a) Fouassier, J. P. Recent Res. Devel. Polym. Sci. 2000, 4, 131.
2. (b) Monroe, B. M.; Weed, G. C. Chem. Rev. 1993, 93, 435.
3. (c) Eaton, D. F. Adv. Photochem. 1985, 13, 427.
4. (d) Davidson, R. S. J. Photochem. Photobiol. A: Chem. 1993, 73, 81.
5. (a) Kawamura, K. (Fuji Photo Film) Japan patent 2,720,195, 1990
6. (a) Kawamura, K. U.S. Patent 5,262,276, 1993
7. Kawamura, K. Chem. Abst. 1990, 113, 207938
8. (b) Bonham, J. A.; Rossman, M. A. (Minnesota Mining and Manufacturing) European Patent 359,431, 1990
9. (b) Bonham, J. A.; Rossman, M. A. U.S. Patent 5,034,526, 1991
10. (b) Bonham, J. A.; Rossman, M. A. Chem. Abst. 1990, 113, 115342
11. (c) Kohler, M.; Ohngemach, J. (Merck) European Patent 354,458, 1990
12. (c) Kohler, M.; Ohngemach, J. Chem. Abst. 1990, 113, 106437
13. (d) Saeva, F. D.; Breslin, D. T. (Eastman Kodak) European Patent 370,693, 1990
14. (d) Saeva, F. D.; Breslin, D. T. Chem. Abst. 1990, 113, 142293
15. (e) Wright, B. B.; DeVoe, R. J. (Minnesota Mining and Manufacturing) European Patent 375,160, 1990
16. (e) Wright, B. B.; DeVoe R. J. Chem. Abst. 1990, 113, 232255.
17. (a) Burget, D.; Fouassier, J. P.; Amat-Guerri, F.; Mallavia, R.; Satre, R. Acta Polym. 1999, 50, 337.
18. (b) Fimia, A.; Sastre, R.; Amat-Guerri, F.; Mallavia, R. Macromolecules 194, 27, 2643.
19. Yamaoka, T.; Kageyama, T.; Takahashi, T.; Urano, T. J. Photopolym. Sci. Technol. 1995, 8, 1.
20. Pawlowski, G.; Dammel, R.; Pryzbilla, K.-J.; Roschert, H.; Spiess, W. J. Photopolym. Sci. Technol. 1991, 4, 389.
21. Yamamoto, M.; Hatano, Y.; Nishijima, Y. Chem. Lett. 1976, 351.
22. Yamamoto, M.; Hatano, Y.; Nishijima, Y. J. Phys. Chem. 1978, 82, 367.
23. Tani, K.; Tohda, Y.; Takemura, H.; Ohikita, H.; Ito, S.; Yamamoto, M. Chem. Comm. 2001, 1914.
24. q could be determined more accurately by calculating the conformational distribution of these compounds and fraction conformation with the end-to-end distance, being shorter than the radius of the active sphere.
25. Kanaya, T.; Hatano, Y.; Yamanoto, M.; Nishijima, Y. Bull. Chem. Soc. Jpn. 1979, 52, 2079.
26. (a) Krongauz, V. V. J. Phys. Chem. 1992 96, 2609.
27. (b) Ratner, M. A.; Mikkelsen, K. V. Chem. Rev. 1987, 87, 113
28. (c) Miller, J. R.; Beitz, J. V.; Huddleston, R. K. J. Am. Chem. Soc. 1984, 106, 5057.
29. (a) Nagai, K.; Takamiya, N.; Kaneko, M. J. Photochem. Photobiol. A Chem. 1994, 84, 271.
30. (b) Nagai, K.; Tsukamoto, J.; Takamiya, N.; Kaneko, M. J. Phys. Chem. 1995, 99, 6648.
31. (a) Ito, H.; Ishikawa, M.; Takada, A.; Kudo, T.; Senda, Y.; Urano, T. Bull. Chem. Soc. Jpn. 2001, 74, 395.
32. (b) Tsurutani, Y.; Ito, H.; Ishikawa, M.; Urano, T. J. Photopolym. Sci. Technol. 2000, 13, 83.
33. (c) Ito, H.; Urano, T.; Nagasaka, S.; Shimizu, S.; Shimizu, M.; Takahara, S.; Yamaoka, T. Bull. Chem. Soc. Jpn. 1997, 70, 1659.
34. Fischer, A. B.; B-Bonte, I. J. Photochem. 1985, 30, 475.
35. Guarr, T.; McGuire, M.; McLendon, G. J. Am. Chem. Soc. 1985, 107, 5104.
36. Miller, J. R.; Peeples, J.; Schmitt, M.; Closs, G. L. J. Am. Chem. Soc. 1982, 104, 6488.
37. (a) Kavarnos, G. J. Fundamentals of Photoinduced Electron Transfer; VCH Publishers: New York, 1993
38. (b) Kavarnos, G. J.; Turro, N. J. Chem. Rev. 1986, 86, 401.
39. Tsuchida, A.; Yamamoto, M.; Nishijima, Y. J. Phys. Chem. 1984, 88, 5062.
40. We could not determine reduction potential of triazine exactly, so we used the value of 2,4,6-tris(trichloromethyl)-1,3,5-triazine reported by Fouassier et al. Grotzinger, C.; Burget, D.; Jacques, P.; Fouassier, J. P. Macromol. Chem. Phys. 2001, 202, 3513.
41. Miller et al. reported quenching radius of <19 Å in the N-Isopropyl-carbazole/TCNE(tetracyanoethylene) system with free-energy change of -2.2 eV in rigid media.
42. Miller, J. R.; Hartman, K. W.; Abrash, S. J. Am. Chem. Soc. 1982, 104, 4296.
43. Pohlers, G.; Sciano, J. C.; Sinta, R.; Brainard, R.; Pai, D. Chem. Mater. 1997, 9, 1353.
44. Oster, G.; Yang, N. L. Chem. Rev. 1968, 125.
45. Koseki, K.; Miyaguchi, S.; Yamaoka, T. Chem. Soc. Jpn. 1986, 1234.
46. Kurdikar, D. L.; Peppas, N. A. Macromolecules 1994, 27, 733, 4084.
47. Encinas, M. V.; Rufs, A. M.; Bertolotti, S.; Previtali, C. M. Macromolecules 2001, 34, 2845.
48. Yamanoto, M.; Nishijima, Y. Kagaku Sousetu 1982, 33, 171.
49. Noguchi, H.; Goto, T.; Yamamoto, M.; Nishijima, Y. Polym. Preprints, Jpn. 1986, 35, 2454.