Comprehensive theoretical study of the conversion reactions of spiropyrans: Substituent and solvent effects

Journal of Physical Chemistry B

Volumn 108, Issue 41, 2004, Pages 16233-16243

  Sheng, Yinghong ^a   Leszczynski, Jerzy ^a   Garcia, Antonio A ^b   Rosario, Rohit ^b   Gust, Devens ^c   Springer, Joseph ^c  

^a JACKSON STATE UNIVERSITY   (United States)

^b Arizona State University   (United States)

^c ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MEROCYANINES (MC); PHOTODECOLORATION; POTENTIAL ENERGY SURFACES (PES); SPIROPYRANS (SP);

ABSORPTION SPECTROSCOPY; ACTIVATION ENERGY; DERIVATIVES; ELECTRIC FIELDS; GROUND STATE; ISOMERIZATION; PHOTOCHEMICAL REACTIONS; POTENTIAL ENERGY; PROBABILITY DENSITY FUNCTION; RAMAN SPECTROSCOPY; REACTION KINETICS; SOLVENTS;

PHOTOCHROMISM;

EID: 7044231519     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0488867     Document Type: Article

References (91)

1. Bertelson, R. C., Photochromic Processes Involving Heterolytic Cleavage. In Techniques of Chemistry; Brown, G. H., Ed.; Wiley-Interscience: 1971; Vol. III, pp 45-433,.
2. Duerr, H.; Bouas-Laurent, H. Photochromism: Molecules and Systems; Elsevier: New York, 1990.
3. Rouhi, A. M. C&EN 2000, 40.
4. Willner, I.; Katz, E.; Willner, B.; Blonder, R.; Heleg-Shabtai, V.; Buckman, A. F. Biosens. Bioelectron. 1997, 12, 337.
5. (a) Willner, I. Acc. Chem. Res. 1997, 30, 347.
6. (b) Willner, I.; Rubin, S.; Shatzmiller, R.; Zor, T. J. Am. Chem. Soc. 1993, 115, 8690.
7. (c) Garcia, A. A.; Cherian, S.; Park, J.; Gust, D.; Jahnke, F.; Rosario, R. J. Phys. Chem. 2000, 104, 103.
8. (a) Guglielmetti, R. In Photochromism-Molecules and Systems, Studies in Organic Chemistry, 40; Durr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990; p 314, p 493, p 879.
9. (b) Organic Photochromic and Thermochromic Compounds, Crano, J. C., Guglielmetti, R., Eds.; Plenum Press: New York, Vol. 1 and 2, 1999.
10. Becker, R. S.; Michl, J. J. Am. Chem. Soc. 1996, 88, 5931.
11. Berkovic, G.; Krongauz, V.; Weiss, V. Chem. Rev. 2000, 100, 1741.
12. (a) Salemi-Delvaux, C.; Luccioni-Houze, B.; Baillet, G.; Giusti, G.; Guglliemetti, R. J. Photochem. Photobiol., A1995, 91, 223.
13. (b) Pimienta, V.; Lavabre, D.; Levy, G.; Samat, A.; Guglielmetti, R.; Micheau, J. C. J. Phys. Chem. 1996, 700, 4485.
14. Tamai, N.; Miyasaka, H. Chem. Rev. 2000, 100, 1875.
15. Campredon, M.; Guglielmetti, R.; Samat, A.; Alberti, A. J. Chem. Phys. 1994, 91, 1830.
16. (a) Gömer, H.; Chibisov, A. K. J. Chem. Soc., Faraday Trans. 1998, 94, 2557.
17. (b) Chibisov, A. K.; Görner, H. Chem. Phys. 1998, 237, 425.
18. Wojtyk, J. T.; Kazmaier, P. M.; Bunde, E. Chem. Mater. 2001, 13, 2547.
19. (a) Görner, H. Chem. Phys. Lett. 1998, 282, 381.
20. (b) Görner, H. Chem. Phys. 1997, 222, 315.
21. (c) Bohne, C.; Fan, M. G.; Li, Z. H.; Laing, Y. C.; Lusztyk, J.; Scaiano, J. C. J. Photochem. Photobiol., A 1992, 66, 79.
22. (a) Görner, H. Chem. Phys. Lett. 1998, 282, 381.
23. (b) Bohne, C.; Fan, M. G.; Li, Z. H.; Liang, Y. C.; Lusztyk, J.; Scaiano, J. C. J. Photochem. Photobiol., A 1992, 66, 79.
24. Malatesta, A.; Neri, C.; Wis, M. L.; Montanari, L.; Millini, R. J. Am. Chem. Soc. 1997, 119, 3451.
25. (a) Görner, H.; Atabekyan, L. S.; Chibisov, A. K. Chem. Phys. Lett. 1996, 260, 59.
26. (b) Salemi, C.; Giusti, G.; Guglielmetti, R. J. Photochem. Photobiol., A 1995, 86, 247.
27. (c) Ricard, R.; Sauvage, P.; Wan, C. S. K.; Weedon, A. C.; Wong, D. F. J. Phys. Chem. 1986, 90, 62.
28. (a) Marfisi, C.; Verlaque, P.; Davidovics, G.; Pourcin, J.; Pizzala, L.; Aycard, J. P.; Bodot, H. J. Phys. Chem. 1983, 87, 5333.
29. (b) Tamaki, T.; Sakuragi, M.; Ichimura, K.; Aori, K. Chem Phys. Lett. 1989, 161, 23.
30. Day, P. N.; Wang, Z.; Patchter, R. J. Phys. Chem. 1995, 99, 9730.
31. Maurel, F.; Aubard, J.; Rajzmann, M.; Guglielmetti, R.; Samat, A. J. Chem. Soc., Perkin Trans. 2 2002, 1307.
32. (a) Le Beuze, A.; Botrel, A.; Appriou, P.; Guglielmetti, R. Tetrahedron 1979, 35, 31.
33. (b) Zerbetto, F.; Monti, S.; Orlandi, G. J. Chem. Soc., Faraday Trans. 2 1984, 80, 1513.
34. Celani, P.; Bernardi, F.; Olivucci, M.; Robb, M. A. J. Am. Chem. Soc. 1997, 119, 10815.
35. (a) Bauschlicher, C. W. Chem. Phys. Lett. 1995, 246, 40.
36. (b) El-Azhary, A. A.; Suter, H. U. J. Phys. Chem. 1996, 100, 15056.
37. (a) Lee, C.; Yang, W.; Parr, R. Phys. Rev. B 1988, 37, 785.
38. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
39. (c) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 90, 5622.
40. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
41. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214.
42. Cances, M. T.; Mennucci, V.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032.
43. (a) Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 66, 217.
44. (b) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
45. (a) Holmén, A.; Broo, A. Int. J. Quantum Chem. 1995, QBS22, 113.
46. (b) Broo, A.; Holmén, A. Chem. Phys. 1996, 211, 147.
47. (a) Roos, B. O. Acc. Chem. Res. 1999, 32, 137.
48. (b) Davidson, E. R. Chem. Rev. 1991, 91, 649.
49. See, for example, Roos, B. O. In Ab initio Methods in Quantum Chemistry II, Lawley, K. P., Ed.; J. Wiley &Sons Ltd: New York, 1987; p 399.
50. Bauernschmitt, R.; Häser, M.; Treuter, O.; Ahlrichs, R. Chem. Phys. Lett. 1997, 264, 573.
51. Straman, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218.
52. Van Caillie, C.; Amos, R. D. Chem. Phys. Lett. 2000, 317, 159.
53. Foresman, J. B.; Head-Gordon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135.
54. (a) Parusel, A. B. J.; Rettig, W.; Sudholt, W. J. Phys. Chem. A 2002, 106, 804.
55. (b) Sheng, Y.; Leszczynski, J. Collect. Czech. Chem. Commun. 2004, 69, 47.
56. 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., Jr.; 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.; Baboul, A. G.; 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.10; Gaussian, Inc., Pittsburgh, PA, 1998.
57. (a) Ernsting, N. P.; Arthen-Engeland, T. J. Phys. Chem. 1991, 95, 5502.
58. (b) Nakatsu, K.; Yoshioka, H. Kwansei Gakuin University Nat. Sci. Rev. 1996, 1, 21.
59. Hobley, J.; Malatesta, V. Phys. Chem. Chem. Phys. 2000, 2, 57.
60. (a) Aubard, J.; Maurel, F.; Buntinx, G.; Guglielmetti, R.; Lévi, G. Mol. Cryst. Liq. Cryst. 2000, 345, 203.
61. (b) Delbaere, S.; Bochu, C.; Azaroual, N.; Buntinx, G.; Vermeersch, G. J. Chem. Soc., Perkin Trans. 2 1997, 1499.
62. Futami, Y.; Chin, M. L. S.; Kudoh, S.; Takayanagi, M.; Nakata, M. Chem. Phys. Lett. 2003, 370, 460.
63. Cottone, G.; Noto, R.; Manna, G. L. Chem. Phys. Lett. 2004, 388, 218.
64. Bercovici, T.; Heiligman-Rim, R.; Fischer, E. Mol. Photochem. 1969, 1, 23.
65. (a) Aramaki, S.; Atkinson, G. H. Chem. Phys. Lett. 1990, 170, 181.
66. (b) Buncel, E.; Kazmeier, P. M.; Keum, S. R. Can. J. Chem. 1991, 69, 1940.
67. (a) Gorman, C. B.; Marder, S. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 11297.
68. (b) Sheng, Y.; Jiang, Y. J. Chem. Soc., Faraday Trans. 1998, 94, 1929.
69. Brooker, L. G. S.; Keyes, G. H.; Sprague, R. H.; Vandyke, R. H.; Vanlare, E.; Vanzandt, G.; White, F. L.; Cressman, H. W. J.; Dent, S. G. J. Am. Chem. Soc. 1951, 73, 5332.
70. (a) Meyers, F.; Marder, S. R.; Pierce, B. M.; Brédas, J. L. J. Am. Chem. Soc. 1994, 116, 10703.
71. (b) Marder, S. R.; Gorman, C. B.; Meyers, F.; Perry, J. W.; Bourhill, G. ; Brédas, J. L.; Pierce, B. M. Science 1994, 265, 632.
72. (c) Sheng, Y.; Jiang, Y.; Wang, X.-C. J. Chem. Soc., Faraday Trans. 1998, 94, 47.
73. (a) Görner, H. Phys. Chem. Chem.Phys. 2001, 3, 416.
74. (b) Sueishi, Y.; Ohcho, M.; Nishimura, N. Bull. Chem. Soc. Jpn. 1985, 58, 2608.
75. (c) Levitus, M.; Talhavini, M.; Negri, R. M.; Atvars, T. D. Z.; Aramendia, P. F. J. Phys. Chem. 1997, 101, 7680.
76. Pfeifer-Fukumura, U. J. Photochem. Photobiol., A. 1997, 111, 145.
77. Flannery, J. B., Jr. J. Am. Chem. Soc. 1968, 90, 5660.
78. Bercovici, T.; Heiligman-Rim, R.; Fischer, E. Mol. Photochem. 1969, 1, 23.
79. (a) Bercovici, T.; Heiligman, R.; Fischer, E. Mol. Photochem. 1969, 1, 23.
80. (b) Bertelson, R. C. Photochromism. In Techniques in Chemistry, Brown, G. H., Ed.; Wiley-Interscience, New York, 1971; Vol. 3, p 45.
81. Kiesswetter, R.; Pustet, N.; Brandi, F.; Mannschreck, A. Tetrahedron: Asymmetry 1999, 10, 4677.
82. Kiesswetter, R.; Burgemeister, T.; Mannschreck, A. Enantiomer 1994, 4, 289.
83. (a) Bearpark, M. J.; Robb, M. A.; Schlegel, H. B. Chem. Phys. Lett. 1994, 225, 269.
84. (b) Bernardi, F.; Olivucci, M.; Robb, M. A. Chem. Soc. Rev. 1996, 25, 321 and references therein.
85. (a) Chibisov, A. K.; Marevtsev, V. S.; Görner, H. J. Photochem. Photobiol., A 2003, 159, 233.
86. (b) Chibisov, A. K.; Görner, H. J. Photochem. Photobiol., A 1997, 105, 261.
87. (c) Chibisov, A. K.; Görner, H. J. Phys. Chem. A 1997, 101, 4305.
88. Favaro, G.; Masetti, F.; Mazzucato, U.; Ottavi, G.; Allegrini, P.; Malatesta, V. J. Chem. Soc., Faraday Trans. 1994, 90, 333.
89. Bercovici, T.; Heiligman-Rim, R.; Fischer, E. Mol. Photochem. 1969, 1, 23.
90. (a) Aramaki, S.; Atkinson, G. H. Chem. Phys. Lett. 1990, 170, 181.
91. (b) Buncel, E.; Kazmeier, P. M.; Keum, S. R. Can. J. Chem. 1991, 69, 1940.