Photoreactivity of a push - pull merocyanine in static electric fields: A three-state model of isomerization reactions involving conical intersections

Journal of Physical Chemistry A

Volumn 113, Issue 36, 2009, Pages 9779-9791

  Xu, X F ^a   Kahan, A ^a   Zilberg, S ^a   Haas, Y ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

BUTADIENE; ELECTRIC FIELDS; ELECTRON TRANSITIONS; INTERSECTIONS; ISOMERIZATION; ISOMERS; SOLVENTS;

CONICAL INTERSECTION; DOUBLE BONDS; ELECTRON ACCEPTOR; ELECTRON DONORS; ELECTROSTATIC CONTROL; EXTERNAL ELECTRIC FIELD; ISOMERIZATION REACTION; MEROCYANINE; POLAR SOLVENTS; RELATIVE ENERGIES; SOLVENT POLARITY; STATIC ELECTRIC FIELDS; THEORETICAL FOUNDATIONS; THREE-STATE MODELS; TRANSITION STATE;

PHOTOCHEMICAL REACTIONS;

EID: 84962449695     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp904097k     Document Type: Article

References (68)

1. Brooker, L. G. S.; Keyes, G. H.; Sprague, R. H.; van Dyke, R. H.; van Lare, E.; van Zandt, G.; White, F. L. J. Am. Chem. Soc. 1951, 73, 5326.
2. Jacques, P. J. Phys. Chem. 1986, 90, 5535.
3. Brooker, L. G. S.; Craig, A. C.; Heseltine, D. W.; Jenkins, P. W.; Lincoln, L. L. J. Am. Chem. Soc. 1965, 87, 2443.
4. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; Verlag Chemie: New York, 1988 and references therein.
5. Morley, J. O.; Morley, R. M.; Fitton, A. L. J. Am. Chem. Soc. 1998, 120, 11479.
6. (a) Baraldi, I.; Brancolinil, G.; Momicchioli, F.; Ponterini, G.; Vanossi, D. Chem Phys. 2003, 288, 309.
7. (b) Rettig, W.; Dekhtyar, M. Chem. Phys. 2003, 293, 75, and references therein.
8. Guillaume, M.; Champagne, B.; Zutterman, F. J. Phys. Chem. A 2006, 110, 13007.
9. Steiner, U.; Abdel-Kader, M. H.; Fisher, P.; Kramer, H. E. A. J. Am. Chem. Soc. 1978, 100, 3190.
10. Tavan, P.; Schulten, K. Chem. Phys. Lett. 1984, 110, 191.
11. Gaines, G. L. Angew. Chem., Int. Ed. Engl. 1987, 26, 341.
12. Burda, C.; Abdel-Kader, M. H.; Link, S.; El-Sayed, M. A. J. Am. Chem. Soc. 2000, 122, 6720.
13. Gómez, I.; Reguero, M.; Robb, M. A. J. Phys. Chem. A 2006, 110, 3986.
14. Mandal, D.; Pal, S. K.; Sukul, D.; Bhattacharyya, K. J. Phys. Chem. A 1999, 103, 8156.
15. Baraldi, I.; Momicchioli, F.; Ponterini, G.; Tatikolov, A. S.; Vanossi, D. Phys. Chem. Chem. Phys. 2003, 5, 979.
16. Marder, S. R.; Gorman, C. B.; Meyers, F.; Perry, J. W.; Bourhill, G.; Bredas, J.L.; Pierce, B. M. Science 1994, 265, 632.
17. Bosshard, C.; Pan, F.; Wong, M. S.; Manetta, S.; Spreiter, R.; Cai, C.; Günter, P.; Gramlich, V. Chem. Phys. 1999, 245, 377.
18. Sainudeen, Z.; Ray, P. C. J. Phys. Chem. A 2005, 109, 9095.
19. Ray, P. C.; Bonifassi, P.; Leszczynski, J. J. Phys. Chem. A 2006, 110, 8963.
20. Mineo, Y.; Itoh, K. J. Phys. Chem. 1991, 95, 2451.
21. Lambert, C.; Stadler, S.; Bourhill, G.; Bräuchie, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 644.
22. Abbotto, A.; Beverina, L.; Bradamante, S.; Facchetti, A.; Klein, C.; Pagani, G. A.; Redi-Abshiro, M.; Wortmann, R. Chem.Eur. J. 2003, 9, 1991.
23. Ray, P. C. Chem. Phys. Lett. 2004, 395, 269.
24. Pan, F.; Wong, M. S.; Gramlich, V.; Bosshard, C.; Günter, P. J. Am. Chem. Soc. 1996, 118, 6315.
25. Albert, I. D. A.; Marks, T. J.; Ratner, M. A. J. Phys. Chem. 1996, 100, 9714.
26. Zilberg, S.; Haas, Y. J. Phys. Chem. A 1998, 102, 10843.
27. Würthner, F.; Archetti, G.; Schmidt, R.; Kuball, H.G. Angew. Chem., Int. Ed. 2008, 47, 4529.
28. Squillacote, M.; Wang, J.; Chen, J. J. Am. Chem. Soc. 2004, 126, 1940.
29. Haas, Y.; Cogan, S.; Zilberg, S. Int. J. Quantum Chem. 2005, 102, 961.
30. Zilberg, S.; Haas, Y. Photochem. Photobiol. Sci. 2003, 2, 1256.
31. Haas, Y.; Cogan, S.; Kahan, A.; Zilberg, S. J. Phys. Chem. A 2008, 112, 5604.
32. Herzberg, G.; Longuet-Higgins, H. C. Discuss. Faraday Soc. 1963, 35, 77.
33. Longuet-Higgins, H. C. Proc. R. Soc. London, Ser. A 1975, 344, 147.
34. Zilberg, S.; Haas, Y. Chem.Eur. J. 1999, 5, 1755.
35. Jasper, A. W.; Kendrick, B. K.; Mead, C. A.; Truhlar, D. G. In Modern Trends in Chemical Reaction Dynamics; Yang, X., Liu, K., Eds.; Advanced Series in Physical Chemistry 14; Word Scientific: River Edge, NJ, 2004; pp 329-391.
36. Tishchenko, O.; Truhlař, D. G.; Ceulemans, A.; Nguyen, M. T. J. Am. Chem. Soc. 2008, 130, 7000.
37. (a) Roos, B. O. Adv. Chem. Phys. 1987, 69, 399.
38. (b) Roos, B. O. In Ab Initio Methods in Quantum Chemistry II; Lawley, K. P., Ed.; Wiley: New York, 1987; p 399.
39. (c) Werner, H.J.; Knowles, P. J. J. Chem. Phys. 1985, 82, 5053.
40. (d) Knowles, P. J.; Werner, H.J. Chem. Phys. Lett. 1985, 115, 259.
41. (e) Busch, T.; Degli Esposti, A.; Werner, H.J. J. Chem. Phys. 1991, 94, 6708.
42. Granovsky, A. A. PC GAMESS, version 7.0. http://classic. chem.msu.su/gran/games/index.html.
43. Werner, H.J.; Knowles, P. J.; Amos, R. D.; Bernhardsson, A.; Berning, A.; Celani, P.; Cooper, D. L.; Deegan, M. J. O.; Dobbyn, A. J.; Eckert, F.; Hampel, C.; Hetzer, G.; Korona, T.; Lindh, R.; Lloyd, A. W.; McNicholas, S. J.; Manby, F. R.; Meyer, W.; Mura, M. E.; Nicklass, A.; Palmieri, P.; Pitzer, R.; Rauhut, G.; Schütz, M.; Schumann, U.; S toll, H.; Stone, A. J.; Tarroni, R.; Thorsteinsson, T. MOLPRO, A Package of Ab Initio Programs, version 2002.1; University of Birmingham: Birmingham, U.K., 2001.
44. The only large scale computation on a merocyanine reported so far is by Robb, J. Phys. Chem. A 2006, 110, 3986. in which a smaller molecule was considered and the reaction was a ring closure one (merocyanine to spiropyran).
45. Boggio-Pasqua, M.; Bearpark, M. J.; Klene, M.; Robb, M. A. J. Chem. Phys. 2004, 120, 7849.
46. Dallos, M.; Lischka, H. Theor. Chem. Ace. 2004, 112, 16.
47. Blomgren, F.; Larsson, S. Int. J. Quantum Chem. 2002, 90, 1536.
48. Bachler, V. J. Comput. Chem. 2003, 25, 343.
49. Ostojiæ B.; Domcke, W. Chem. Phys. 2001, 269, 1.
50. Serrano-Andrés, L.; Roos, B. O.; Merchán, M. Theor. Chim. Acta. 1994, 87, 387.
51. Serrano-Andrés, L.; Merchán, M.; Nebot-Gil, I.; Lindh, R.; Roos, B. O. J. Chem. Phys. 1993, 98, 3151.
52. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A., Jr. J. Comput. Chem. 1993, 14, 1347.
53. Dick, B. J. Chem. Theory Comput. 2009, 5, 116.
54. See also: Dick, B.; Haas, Y.; Zilberg, S. Chem. Phys. 2008, 347, 65.
55. (a) Kirkwood, J. J. Chem. Phys. 1934, 2, 351.
56. (b) Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486.
57. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
58. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785
59. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; 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.; Nanavakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; HeadGordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03, revision B.03; Gaussian, Inc.: Pittsburgh, PA, 2003.
60. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.
61. Willetts, A.; Rice, J. E. J. Chem. Phys. 1993, 99, 426.
62. All comparisons with experiments were done with data obtained for Brooker's merocyanine rather than I.
63. Baumann, W. Z. Naturforscher 1983, 38a, 995.
64. Bletz, M.; Pfeifer-Fukumura, U.; Kolb, U.; Baumann, W. J. Phys. Chem. A 2002, 106, 2232.
65. Meyers, F.; Marder, S. R.; Pierce, B. M.; Brédas, J. L. J. Am. Chem. Soc. 1994, 116, 10703, and ref 25 therein.
66. The Cs restriction simulates the experimental situation in a solid matrix, in which torsion is inhibited, as outlined in the Introduction.
67. Fuss, W.; Haas, Y.; Zilberg, S. Chem. Phys. 2000, 259, 273.
68. Ischenko, A. A.; Kulinich, A. V.; Bondarev, S. L.; Knyukshto, V. N. J. Phys. Chem. A 2007, 111, 13629.