Quantum chemical study of the photocoloration reaction in the napthoxazine series

Journal of Physical Chemistry A

Volumn 110, Issue 14, 2006, Pages 4759-4771

  Maurel, F ^a   Aubard, J ^a   Millie, P ^b   Dognon, J P ^c   Rajzmann, M ^d   Guglielmetti, R ^d   Samat, A ^d  

^a UNIVERSITÉ PARIS DIDEROT   (France)

^b UNIVERSITÉ PARIS SUD   (France)

^c CEA SACLAY   (France)

^d AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; COLOR; ELECTRIC EXCITATION; ISOMERS; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY;

ENERGY PROFILE; EXCITATION ENERGIES; NAPTHOXAZINE; QUANTUM YIELD;

PHOTOCHEMICAL REACTIONS;

EID: 33646272430     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp054976f     Document Type: Article

References (58)

1. (a) Bertelson, R. C. In Photochromism; Brown, G. H., Ed.; Techniques in Chemistry; Wiley-Interscience: New York, 1971; Vol. 3, p 45.
2. (b) Photochromism: Molecules & Systems; Durr, H., Bouas-Laurent, H., Eds.; Elsevier: New York, 1990.
3. Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R. J., Eds.; Kluwer Academic/Plenum Publishers: New York, 1999.
4. Chu, N. Y. C. In Photochromism: Molecules & Systems; Durr, H., Bouas-Laurent, H., Eds.; Elsevier: New York, 1990; p 493.
5. Maeda, S. In Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R. J., Eds.; Kluwer Academic/Plenum Publishers: New York, 1999; Vol. 1, pp 85-109.
6. Crano, J. C.; Kwak, W. S.; Welch, C. N. Applied Photochromic Polymer Systems; McArdle, C. B., Ed.; Blackie: London, 1992; Chapter 2, p 31.
7. Berkovic, G.; Krongauz, V.; Weiss, V. Chem. Rev. 2000, 100, 1741.
8. Samat, A.; Lokshin, V. In Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R. J., Eds.; Kluwer Academic/Plenum Publishers: New York, 1999; Vol. 2, p 415.
9. Kellmann, A.; Tfibel, F.; Dubest, R.; Levoir, P.; Aubard, J.; Pottier, E.; Guglielmetti, R. J. Photochem. Photobiol., A 1989, 49, 63.
10. Schneider, S. Z. Phys. Chem. 1987, 154, 91.
11. Wilkinson, F.; Worarall, D. R.; Hobley, J.; Jancsen, L.; Williams, S. L.; Langley, A. J.; Matousek, P. J. Chem. Soc., Faraday Trans. 1996, 92, 1331.
12. Tamai, N.; Masuhara, H. Chem. Phys. Lett. 1992, 191, 189.
13. Antipin, S. A.; Petrukhin, A. N.; Gostev, F. E.; Marevtsev, V. S.; Titov, A. A.; Barachevsky, V. A.; Strokach, Yu. P.; Sarkisov, O. M. Chem. Phys. Lett. 2000, 331, 378.
14. Aubard, J.; Maurel, F.; Buntinx, G.; Poizat, O.; Lévi, G.; Guglielmetti, R.; Samat, A. Mol. Cryst. Liq. Cryst. 2000, 345, 215.
15. Aramaki, S.; Atkinson, G. H. Chem. Phys. Lett. 1990, 170, 181.
16. Aubard, J.; Maurel, F.; Buntinx, G.; Guglielmetti, R.; Lévi, G. Mol. Cryst. Liq. Cryst. 2000, 345, 203.
17. Aubard, J. In Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R. J., Eds.; Kluwer Academic/Plenum Publishers: New York, 1999; Vol. 2, pp 357-392.
18. Nakamura, S.; Uchida, K.; Murakami, A.; Irie, M. J. Org. Chem. 1993, 58, 5543.
19. Maurel, F.; Aubard, J.; Rajzmann, M.; Guglielmetti, R.; Samat, A. J. Chem. Soc., Perkin Trans. 2 2002, 1307.
20. Celani, P.; Bernardi, F.; Olivucci, M.; Robb, M. A. J. Am. Chem. Soc. 1997, 119, 10815.
21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.1; Gaussian, Inc.: Pittsburgh, PA, 1998.
22. König, G.; Stollhoff, G. Phys. Rev. Lett. 1990, 65, 1239.
23. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
24. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
25. (a) Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 66, 217.
26. (b) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
27. Dewar, M. J. S.; Zoebish, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
28. AMPAC 7.0 Code; Semichem, Inc.: Shawnes, KS 1992-2003.
29. (a) Agmon, A.; Rettig, W.; Groth, C. J. Am. Chem. Soc. 2002, 124, 1089.
30. (b) Gedeck, P.; Schneider, S. J. Photochem. Photobiol, A 1999, 121, 7.
31. Lambert, C.; Risko, C.; Coropceanu, V.; Schelter, J.; Amthor, S.; Gruhn, N. E.; Durivage, J. C.; Bredas, J. L. J. Am. Chem. Soc. 2005, 127, 8508.
32. (a) Mommicchioli, F.; Baraldi, I.; Bruni, M. C. Chem. Phys. 1982, 70, 161.
33. (b) Mommicchioli, F.; Baraldi, I.; Bruni, M. C. Chem. Phys. 1983, 82, 229.
34. Huron, B.; Malrieu, J. P.; Rancurel, P. J. Chem. Phys. 1973, 58, 5745.
35. Germain, A.; Millie, P. Chem. Phys. 1997, 219, 265.
36. Maurel, F.; Samat, A.; Guglielmetti, R.; Aubard, J. Mol. Cryst. Liq. Cryst. 2000, 345, 75.
37. (a) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454.
38. (b) Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439.
39. Stratman, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218.
40. (a) Tyer, N. W., Jr.; Becker, R. S. J. Am. Chem. Soc. 1970, 92, 1289.
41. (b) Tyer, N. W., Jr.; Becker, R. S. J. Am. Chem. Soc. 1970, 92, 1295.
42. Ernsting, N. P.; Arthen-Engeland, Th. J. Phys. Chem. 1991, 95, 5502.
43. Slaughter, B. D.; Allen, M. W.; Lushington, G. H.; Johnson, K. J. Phys. Chem. A 2003, 170, 5670.
44. Del Bene, J. E. Chem. Phys. Lett. 1976, 44, 512.
45. Zyubin, A. S.; Mebel, A. M. J. Comput. Chem. 2003, 24, 692.
46. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
47. Delbaere, S.; Bochu, C.; Azaroual, N.; Buntinx, G.; Vermeersch, G. J. Chem. Soc., Perkin Trans. 2 1997, 1499.
48. (a) Sheng, Y.; Lesczczynski, J.; Garcia, A. A.; Rosario, R.; Gust, D.; Springer, J. J. Phys. Chem. B 2004, 108, 16233.
49. (b) Minkin, V.; Metelitsa, A. V.; Dorognan, I. V.; Lukyanov, B. S.; Besugliy, S. O.; Micheau, J.-C. J. Phys. Chem. A 2005, 109, 9605.
50. Millini, R.; Del Piero, G.; Allegrini, P.; Crisci, L.; Malatesta, V. Acta Crystallogr., Sect. C 1991, 47, 2567.
51. Bohne, C.; Fan, M. G.; Li, Z. J.; Luszlyk, J.; Scaiano, J. C. J. Chem Soc., Chem. Commun. 1990, 571.
52. Chibisov, A. K.; Marevtsev, V. S.; Görner, H. J. Photochem. Photobiol. 2003, 159, 233.
53. (a) Zheng-Li, C.; Reimers, J. R. J. Chem. Phys. 2000, 112, 527-530.
54. (b) Zheng-Li, C.; Tozer, D. J.; Reimers, J. R. J. Chem. Phys. 2000, 112, 7084.
55. Chibisov, A. K.; Görner, H. J. Phys. Chem. A 1997, 101, 4305.
56. Pearl, G. M.; Zerner, M. C.; Broo, A.; McKelvey, J. J. Comput. Chem. 1998, 19, 781.
57. Metelitsa, A. V.; Lokshin, V.; Micheau, J. C.; Samat, A.; Guglielmetti, R.; Minkin, V. I. Phys. Chem. Chem. Phys. 2002, 18, 4340.
58. Migani, A.; Gentili, P. L.; Negri, F.; Olivucci, M.; Romani, A.; Favaro, G.; Becker, R. S. J. Phys. Chem. A 2005, 109, 8684.