Substituent-dependent photoinduced intramolecular charge transfer in N-aryl-substituted trans-4-aminostilbenes

Journal of the American Chemical Society

Volumn 126, Issue 39, 2004, Pages 12325-12335

  Yang, Jye Shane ^a   Liau, Kang Ling ^a   Wang, Chin Min ^a   Hwang, Chung Yu ^a  

^a NATIONAL CENTRAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; HYDROGEN; MATHEMATICAL MODELS; NITROGEN COMPOUNDS; PHOTOCHEMICAL REACTIONS; SUBSTITUTION REACTIONS;

METHOXYCARBONYL; PHOTOCHEMICAL BEHAVIOR; TRIFLUOROMETHYL; TWISTED INTRAMOLECULAR CHARGE TRANSFER (TICT);

CHARGE TRANSFER;

4 AMINOSTILBENE; CARBON; CARBONYL DERIVATIVE; FUNCTIONAL GROUP; METHOXY GROUP; METHOXYCARBONYL DERIVATIVE; METHYL GROUP; N,N DIMETHYLAMINOSTILBENE DERIVATIVE; NITRILE; NITROGEN; OXYGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SOLVENT; STILBENE DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; COVALENT BOND; EXCITED STATE; INTRAMOLECULAR CHARGE TRANSFER; MODEL; PHOTOCHEMISTRY; QUANTUM CHEMISTRY; TWISTED INTRAMOLECULAR CHARGE TRANSFER STATE;

EID: 4644277919     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047604d     Document Type: Article

References (99)

1. (a) Marder, S. R.; Perry, J. W. Science 1994, 263, 1706-1707.
2. (b) Verbiest, T.; Burland, D. M.; Jurich, M. C.; Lee, V. Y.; Miller, R. D.; Volksen, W. Science 1995, 268, 1604-1606.
3. (c) Whitaker, C. M.; Patterson, E. V.; Kott, K. L.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 9966-9973.
4. (d) Nandi, P. K.; Mandal, K.; Kar, T. Chem. Phys. Lett. 2003, 381, 230-238.
5. (a) Albota, M.; Beljonne, D.; Brédas, J. L.; Ehrlich, J. E.; Fu, J.-Y.; Heikal, A. A.; Hess, S. E.; Kogej, T.; Levin, M. D.; Marder, S. R.; McCord-Maughon, D.; Perry, J. W.; Röckel, H.; Rumi, M.; Subramaniam, G.; Webb, W. W.; Wu, X.-L.; Xu, C. Science 1998, 281, 1653-1656.
6. (b) Kogej, T.; Beljonne, D.; Meyers, F.; Perry, J. W.; Marder, S. R.; Brédas, J. L. Chem. Phys. Lett. 1998, 298, 1-6.
7. (c) Reinhardt, B. A.; Brott, L. L.; Clarson, S. J.; Dillard, A. G.; Bhatt, J. C.; Kannan, R.; Yuan, L.; He, G. S.; Prasad, P. N. Chem. Mater. 1998, 10, 1863-1874.
8. (d) Lee, W.-H.; Lee, H.; Kim, J.-A.; Choi, J.-H.; Cho, M.; Jeon, S.-J.; Cho, B. R. J. Am. Chem. Soc. 2001, 123, 10658-10667.
9. (e) Wang, X.; Zhou, Y.; Zhou, G.; Jiang, W.; Jiang, M. Bull. Chem. Soc. Jpn. 2002, 75, 1847-1854.
10. La Clair, J. J. Angew. Chem., Int. Ed. 1999, 38, 3045-3047.
11. (a) Morozumi, T.; Anada, T.; Nakamura, H. J. Phys. Chem. B 2001, 105, 2923-2931.
12. (b) Xiao, Y.; Qian, X. Tetrahedron Lett. 2003, 44, 2087-2091.
13. (c) Yang, J.-S.; Hwang, C.-Y.; Hsieh, C.-C.; Chiou, S.-Y. J. Org. Chem. 2004, 69, 719-726.
14. (d) Yang, J.-S.; Lin, Y.-D.; Lin, Y.-H.; Liao, F.-L. J. Org. Chem. 2004, 69, 3517-3525.
15. La Clair, J. J. Angew. Chem., Int. Ed. 1998, 37, 325-329.
16. (a) Lippert, E.; Lüder, W.; Moll, F.; Nägele, W.; Boos, H.; Prigge, H.; Seibold-Blankenstein, I. Angew. Chem. 1961, 73, 695-706.
17. (b) Lippert, E.; Lüder, W.; Boos, H. In Advances in Molecular Spectroscopy; Mangini, A., Ed.; Pergamon Press: Oxford, 1962; pp 443-457.
18. (a) Rotkiewicz, K.; Grellmann, K. H.; Grabowski, Z. R. Chem. Phys. Lett. 1973, 19, 315-318.
19. (b) Grabowski, Z. R.; Rotkiewicz, K.; Siemiarczuk, A.; Cowley, D. J. Baumann, W. Nouv. J. Chim. 1979, 3, 443-454.
20. (c) Rettig, W. Angew. Chem., Int. Ed. Engl. 1986, 25, 971-988.
21. (d) Rettig, W.; Maus, M. In Conformational Analysis of Molecules in Excited States; Waluk, J., Ed.; Wiley-VCH: New York, 2000; Chapter 1, pp 1-55.
22. (e) Grabowski, Z. R.; Rotkiewicz, K. Chem. Rev. 2003, 103, 3899-4031.
23. (a) Rettig, W.; Bliss, B.; Dirnberger, K. Chem. Phys. Lett. 1999, 305, 8-14.
24. (b) Rettig, W.; Zietz, B. Chem. Phys. Lett. 2000, 317, 187-196.
25. (c) Rettig, W.; Lutze, S. Chem. Phys. Lett. 2001, 341, 263-271.
26. (d) Dobkowski, J.; Wójcik, J.; Kozminski, W.; Kolos, R.; Waluk, J.; Michl, J. J. Am. Chem. Soc. 2002, 124, 2406-2407.
27. (e) Rotkiewicz, K.; Rettig, W.; Detzer, N.; Rothe, A. Phys. Chem. Chem. Phys. 2003, 5, 998-1002.
28. (f) Dobkowski, J.; Michl, J.; Waluk, J. Phys. Chem. Chem. Phys. 2003, 5, 1027-1031.
29. (g) Kwok, W. M.; Ma, C.; George, M. W.; Grills, D. C.; Matousek, P.; Parker, A. W.; Phillips, D.; Toner, W. T.; Towrie, M. Phys. Chem. Chem. Phys. 2003, 5, 1043-1050.
30. (h) Saigusa, H.; Iwase, E.; Nishimura, M. J. Phys. Chem. A 2003, 107, 3759-3763.
31. (a) Mennucci, B.; Toniolo A.; Tomasi, J. J. Am. Chem. Soc. 2000, 122, 10621-10630.
32. (b) Parusel, A. B. J.; Rettig, W.; Sudholt, W. J. Phys. Chem. A 2002, 106, 804-815.
33. (c) Jödicke, C. J.; Lüthi, H. P. J. Am. Chem. Soc. 2003, 125, 252-264.
34. (d) Jödicke, C. J.; Lüthi, H. P. J. Chem. Phys. 2003, 119, 12852-12865.
35. (e) Rappoport, D.; Furche, F. J. Am. Chem. Soc. 2004, 126, 1277-1284.
36. (a) Serrano-Andrés, L.; Merchán, M.; Roos, B. O.; Lindh, R. J. Am. Chem. Soc. 1995, 117, 3189-3204.
37. (b) Jödicke, C. J.; Lüthi, H. P. J. Chem. Phys. 2002, 117, 4146-4156.
38. (c) Jödicke, C. J.; Lüthi, H. P. J. Chem. Phys. 2002, 117, 4157-4167.
39. (a) Sobolewski, A. L.; Domcke, W. Chem. Phys. Lett. 1996, 250, 428-436.
40. (b) Sobolewski, A. L.; Domcke, W. Chem. Phys. Lett. 1996, 259, 119-127.
41. Schuddeboom, W.; Jonker, S. A.; Warman, J. M.; Leinhos, U.; Kühnle, W.; Zachariasse, K. A. J. Phys. Chem. 1992, 96, 10809-10819.
42. (a) von der Haar, T.; Hebecker A.; Il'ichev, Y.; Jiang, Y.-B.; Kühnle, W.; Zachariasse, K. A. Recl. Trav. Chim. Pays-Bas 1995, 114, 430-442.
43. (b) Zachariasse, K. A.; Grobys, M.; von der Haar, T.; Hebecker A.; Il'ichev, Y. V.; Jiang, Y.-B.; Morawski, O.; Kühnle, W. J. Photochem. Photobiol. A: Chem. 1996, 102, 59-70.
44. (c) Zachariasse, K. A.; Grobys, M.; von der Haar, T.; Hebecker A.; Il'ichev, Y. V.; Morawski, O.; Rückert, I.; Kühnle, W. J. Photochem. Photobiol. A: Chem. 1997, 105, 373-383.
45. (d) Il'ichev, Y. V.; Kühnle, W.; Zachariasse, K. A. J. Phys. Chem. A 1998, 102, 5670-5680.
46. (e) Zachariasse, K. A. Chem. Phys. Lett. 2000, 320, 8-13.
47. (f) Demeter, A.; Zachariasse, K. A. Chem. Phys. Lett. 2003, 380, 699-703.
48. (g) Zachariasse, K. A.; Druzhinin, S. I.; Bosch, W.; Machinek, R. J. Am. Chem. Soc. 2004, 126, 1705-1715.
49. (a) Saltiel, J.; Charlton, J. L. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 3, pp 25-89.
50. (b) Saltiel, J.; Sun, Y.-P. In Photochromism, Molecules and Systems; Dürr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990; pp 64-164.
51. (c) Waldeck, D. H. Chem. Rev. 1991, 91, 415-436.
52. (d) Görner, H.; Kuhn, H. J. Adv. Photochem. 1995, 19, 1-117.
53. Létard, J.-F.; Lapouyade, R.; Rettig W. J. Am. Chem. Soc. 1993, 115, 2441-2447.
54. (a) Rettig, W.; Majenz, W. Chem. Phys. Lett. 1989, 154, 335-341.
55. (b) Lapouyade, R.; Czeschka, K.; Majenz, W.; Rettig, W.; Gilabert, E.; Rullière, C. J. Phys. Chem. 1992, 96, 9643-9650.
56. (c) Abraham, E.; Oberlé, J.; Jonusauskas, G.; Lapouyade, R.; Rullière, C. J. Photochem. Photobiol. A: Chem. 1997, 105, 101-107.
57. (d) Papper, V.; Pines, D.; Likhtenshtein, G.; Pines, E. J. Photochem. Photobiol. A: Chem. 1997, 111, 87-96.
58. (e) Abraham, E.; Oberlé, J.; Jonusauskas, G.; Lapouyade, R.; Rullière, C. Chem. Phys. 1997, 214, 409-423.
59. (f) Pines, D.; Pines, E.; Rettig, W. J. Phys. Chem. A 2003, 107, 236-242.
60. (a) Amatatsu, Y. Theor. Chem. Acc. 2000, 103, 445-450.
61. (b) Amatatsu, Y. Chem. Phys. 2001, 274, 87-98.
62. (a) Gruen, H.; Görner, H. J. Phys. Chem. 1989, 93, 7144-7152.
63. (b) Lapouyade, R.; Kuhn, A.; Létard, J.-F.; Rettig, W. Chem. Phys. Lett. 1993, 208, 48-58.
64. Létard, J.-F.; Lapouyade, R.; Rettig, W. Chem. Phys. Lett. 1994, 222, 209-216.
65. Seydack, M.; Bendig, J. J. Phys. Chem. A 2001, 105, 5731-5733.
66. (a) Il'ichev, Y. V.; Kühnle, W.; Zachariasse, K. A. Chem. Phys. 1996, 211, 441-453.
67. (b) Kovalenko, S. A.; Schanz, R.; Senyushkina, T. A.; Ernsting, N. P. Phys. Chem. Chem. Phys. 2002, 4, 703-707.
68. Eilers-König, N.; Kühne, T.; Schwarzer, D.; Vöhringer, P.; Schroeder, J. Chem. Phys. Lett. 1996, 253, 69-76.
69. Rechthaler, K.; Köhler, G. Chem. Phys. Lett. 1996, 250, 152-158.
70. (a) Lewis, F. D.; Kalgutkar, R. S.; Yang, J.-S. J. Am. Chem. Soc. 1999, 121, 12045-12053.
71. (b) Lewis, F. D.; Weigel, W. J. Phys. Chem. A 2000, 104, 8146-8153.
72. (c) Lewis, F. D.; Weigel, W.; Zuo, X. J. Phys. Chem. A 2001, 105, 4691-4696.
73. Yang, J.-S.; Chiou, S.-Y.; Liau, K.-L. J. Am. Chem. Soc. 2002, 124, 2518-2527.
74. Yang, J.-S.; Wang, C.-M.; Hwang, C.-Y.; Liau, K.-L.; Chiou, S.-Y. Photochem. Photobiol. Sci. 2003, 2, 1225-1231.
75. (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
76. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
77. Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673-1674.
78. Gangjee, A.; Vasudevan, A.; Queener, S. F. J. Med. Chem. 1997, 40, 479-485.
79. Ikan, R.; Rapaport, E. Tetrahedron 1967, 23, 3823-3827.
80. Plentl, A. A.; Bogert, M. T. J. Am. Chem. Soc. 1941, 63, 989-995.
81. Compound 5OM is weakly fluorescent and very sensitive to the room light, and more than one photoproduct has been detected by HPLC.
82. Jutz, C. Adv. Org. Chem. 1976, 9, 225-342.
83. Wadsworth, W. S., Jr. Org. React. 1977, 25, 73-253.
84. Zerner, M. C.; Leow, G. H.; Kirchner, R. F.; Mueller-Westerhoff, U. T. J. Am. Chem. Soc. 1980, 102, 589-599.
85. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
86. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; Harper & Row: New York, 1987; p 144.
87. See Supporting Information for details.
88. (a) Liptay, W. Z. Z. Naturforsch. 1965, 20a, 1441.
89. (b) Lippert, E. Z. Elecktrochem. 1957, 61, 962-975.
90. (c) Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1956, 29, 465-470.
91. Marcus, Y. Chem. Soc. Rev. 1993, 409-416.
92. Ma, L.-H.; Chen, Z.-B.; Jiang, Y.-B. Chem. Phys. Lett. 2003, 372, 104-113.
93. (a) Maliakal, A.; Lem, G.; Turro, N. J.; Ravichandran, R.; Suhadolnik, J. C.; DeBellis, A. D.; Wood, M. G.; Lau, J. J. Phys. Chem. A 2002, 106, 7680-7689.
94. (b) Nad, S.; Kumbhakar, M.; Pal, H. J. Phys. Chem. A 2003, 107, 4808-4816.
95. (a) Saltiel, J.; D'Agostino, J. T. J. Am. Chem. Soc. 1972, 94, 6445-6456.
96. (b) Rothenberger, G.; Negus, D. K.; Hochstrasser, R. M. J. Chem. Phys. 1983, 79, 5360-5367.
97. In view of the inherent difference in electronic structures among donor-only, donor-acceptor-type, and donor-donor-type aminostilbenes, any comparison to be made between 1 and the N-alkyl derivatives should be more appropriately restricted to the same type of aminostilbenes, viz., the donor-only DS.
98. Dawson, W. R.; Windsor, M. W. J. Phys. Chem. 1968, 72, 3251-3260.
99. Malkin, S.; Fischer, E. J. Phys. Chem. 1964, 68, 1153-1163.