Photoisomerization of all-trans-1,6-diphenyl-1,3,5-hexatriene. Temperature and deuterium isotope effects

Journal of Physical Chemistry A

Volumn 107, Issue 18, 2003, Pages 3178-3186

  Saltiel, Jack ^a   Krishnamoorthy, Govindarajan ^a   Huang, Zhennian ^a   Ko, Dong Hoon ^a   Wang, Shujun ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOISOMERIZATION;

ACETONITRILE; CHEMICAL BONDS; DEUTERIUM; ENERGY GAP; ISOMERIZATION; SUBSTITUTION REACTIONS;

AROMATIC HYDROCARBONS;

EID: 0038334581     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp021540g     Document Type: Article

References (84)

1. Hudson, B. S.; Kohler, B. E. Annu. Rev. Phys. Chem. 1974, 25, 437-460.
2. Hudson, B. S.; Kohler, B. E.; Schulten, K. In Excited States; Lim, E. C., Ed.; Academic Press: New York, 1982; Vol. 6, pp 1-95.
3. Saltiel, J.; Sun, Y.-P. In Photochromism, Molecules and Systems; Dürr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990; pp 64-164.
4. (a) Pfeiffer, M.; Werncke, W.; Hogiu, S.; Kummrow, A.; Lau, A. Chem. Phys. Lett. 1998, 295, 56-62.
5. (b) Hogiu, S.; Werncke, W.; Pfeiffer, M.; Lau, A. Chem. Phys. Lett. 1999, 303, 218-222.
6. (c) Werncke, W.; Hogiu, S.; Pfeiffer, M.; Lau, A.; Kummrow, A. J. Phys. Chem. A 2000, 104, 4211-4217.
7. Hilinski, E. F.; McGowan, W. M.; Sears, D. F., Jr.; Saltiel, J. J. Phys. Chem. 1996, 100, 3308-3311.
8. Yee, W. A.; O'Neil, R. H.; Lewis, J. W.; Zhang, J. Z.; Kliger, D. S. Chem. Phys. Lett. 1997, 276, 430-434.
9. Hogiu, S.; Werncke, W.; Pfeiffer, M.; Lau, A.; Steinke, T. Chem. Phys. Lett. 1998, 287, 8-16.
10. Itoh, T.; Kohler, B. E. J. Phys. Chem. 1987, 91, 1760-1764.
11. Orlandi, G.; Siebrand, W. Chem. Phys. Lett. 1974, 30, 352-354.
12. Birks, J. B.; Birch, D. J. S. Chem. Phys. Lett. 1975, 31, 608-610.
13. (b) Birks, J. B.; Tripathy, G. N. R.; Lumb, M. D. Chem. Phys. 1978, 33, 185-194.
14. (c) Birks, J. B. Chem. Phys. Lett. 1978, 54, 430-434.
15. Saltiel, J.; Ko, D.-H.; Fleming, A. S. J. Am. Chem. Soc. 1994, 116, 4099-5000.
16. Saltiel, J.; Wang, S.; Watkins, L. P.; Ko, D.-H. J. Phys. Chem. A 2000, 104, 11443-11450.
17. Cehelnik, E. D.; Cundall, R. B.; Lockwood, J. R.; Palmer, T. J. J. Phys. Chem. 1975, 79, 1369-1380.
18. (a) Schael, F. W. Dissertation; Technische Universität: Carlo-Wilhelmina zu Braunschweig, Germany, 1995.
19. (b) Schael, F.; Löhmannsröben, H.-G. Chem. Phys. 1996, 206, 193-210.
20. Saltiel, J.; Wang, S.; Ko, D.-H.; Gormin, D. A. J. Phys. Chem. A 1998, 702, 5383-5392.
21. Nüchter, U.; Zimmermann, G.; Francke, V.; Hopf, H. Liebigs Ann. Recl. 1997, 1505-1515.
22. Saltiel, J.; Crowder, J. M.; Wang, S. J. Am. Chem. Soc. 1999, 121, 895-902.
23. Vollhardt, K. P. C.; Winn, L. S. Tetrahedron Lett. 1985, 26, 709-12.
24. Moses, F. G.; Liu, R. S. H.; Monroe, B. M. Mol. Photochem. 1969, 1, 245-249.
25. Hammond, H. A.; DeMeyer, D. E.; Williams, J. L. R. J. Am. Chem. Soc. 1969, 91, 5180-5181.
26. Valentine, D., Jr.; Hammond, G. S. J. Am. Chem. Soc. 1972, 94, 3449-3454.
27. Saltiel, J.; Sears, D. F., Jr.; Ko, D.-H.; Park, K. M. In Handbook of Organic Photochemistry; Horspool, W. M., Song, P.-O., Eds.; CRC Press: London, 1995; Section 1, pp 3-15.
28. Melhuish, W. H. J. Phys. Chem. 1961, 65, 229-235.
29. Meech, S. R.; Phillips, D. J. Photochem. 1983, 23, 193-217.
30. Saltiel, J.; Charlton, J. L. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; 1980; Vol. III, pp 25-89.
31. (a) Ko, D.-H. Ph.D. Dissertation, Florida State University, Tallahassee, FL, 1997.
32. (b) Wang, S. Ph.D. Dissertation, Florida State University, Tallahassee, FL, 1998.
33. (a) Robinson, G. W.; Frosch, R. P. J. Chem. Phys. 1962, 37, 1962.
34. (b) Robinson, G. W.; Frosch, R. P. J. Chem. Phys. 1963, 38, 1187.
35. Lower, S. K.; El-Sayed, M. A. Chem. Rev. 1966, 66, 199.
36. Jortner, J.; Rice, S. A.; Hochstrasser, R. M. Adv. Photochem. 1969, 7, 149-309.
37. Siebrand, W. The Triplet State; Beirut Symposium, 1967; Zahlan, A. B., Ed.: Cambridge University Press: Cambridge, 1967; p 31.
38. Hirota, N.; Hutchison, C. A., Jr. J. Chem. Phys. 1967, 46, 1561.
39. (a) Martin, T. E.; Kalantar, A. H. J. Chem. Phys. 1968, 48, 4996.
40. (b) Martin, T. E.; Kalantar, A. H. Chem. Phys. Lett. 1968, 1, 623.
41. (a) Watts, R. J.; Strickler, S. J. J. Chem. Phys. 1968, 49, 3967.
42. (b) Burke, T. D.; Watts, R. J.; Strickler, S. J. J. Chem. Phys. 1969, 50, 5425.
43. Simpson, J. D.; Offen, H. W.; Burr, J. D. Chem. Phys. Lett. 1969, 2, 383.
44. Henry, B. R.; Charlton, J. L. J. Am. Chem. Soc. 1973, 95, 2782-2785.
45. Henry, B. R.; Siebrand, W. J. Chem. Phys. 1971, 54, 1072.
46. (b) Henry, B. R.; Siebrand, W. Chem. Phys. Lett. 1969, 3, 327.
47. Saltiel, J.; D'Agostino, J. T.; Herkstroeter, W. G.; Saint-Ruf, G.; Buu-Hoï, N. P. J. Am. Chem. Soc. 1973, 95, 2543-2549.
48. Caldwell, R. A. Pure Appl. Chem. 1984, 56, 1167-1177.
49. Heinrich, G.; Holzer, G.; Blume, H.; Schulte-Frohlinde, D. Z. Naturforsch. B 1970, 25, 496.
50. Courtney, S. H.; Balk, M. W.; Phillips, L. A.; Web, S. P.; Yang, D.; Levy, D. H.; Fleming, G. R. J. Chem. Phys. 1988, 89, 6697.
51. Saltiel, J.; Waller, A. S.; Sears, D. F., Jr.; Garrett, C. Z. J. Phys. Chem. 1993, 97, 2515-2522.
52. 30
53. Felker, P. M.; Zewail, A. H. J. Phys. Chem. 1985, 89, 5402-5411.
54. Negri, F.; Orlandi, G. J. Phys. Chem. 1991, 95, 748-757 and references cited.
55. Saltiel, J.; Waller, A. S.; Sears, D. F., Jr. J. Am. Chem. Soc. 1993, 115, 2453-2464.
56. Caldwell, R. A.; Misawa, H.; Healy, E. F.; Dewar, M. J. S. J. Am. Chem. Soc. 1987, 109, 6869-6870.
57. Olson, L. P.; Niwayama, S.; Yoo, H.-Y.; Houk, K. N.; Harris, N. J.; Gajewski, J. J. J. Am. Chem. Soc. 1996, 118, 886-892.
58. Brouwer, A. M.; Cornelisse, J.; Jacobs, H. J. C. J. Photochem. Pholobiol. A: Chem. 1988, 42, 313-320.
59. Saltiel, J. J. Am. Chem. Soc. 1968, 90, 6394-6400.
60. Saltiel, J.; Sears, D. F., Jr.; Sun, Y.-P.; Choi, J.-O. J. Am. Chem. Soc. 1992, 114, 3607-3612.
61. (a) Siebrand, W. J. Chem. Phys. 1967, 46, 440; 47, 2411.
62. (a) Siebrand, W. J. Chem. Phys. 1967, 46, 440; 47, 2411.
63. (b) Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules; VCH Publisher: New York, 1995; p 254.
64. Datta, P.; Goldfarb, T. D.; Boikess, R. S. J. Am. Chem. Soc. 1971, 93, 5189-5193.
65. (a) Olivucci, M.; Bernardi, F.; Celani, P.; Ragazos, I. N.; Robb, M. A. J. Am. Chem. Soc. 1994, 116, 1077-1085.
66. (b) Celani, P.; Garavelli, M.; Ottani, S.; Bernardi, F.; Robb, M. A.; Olivucci, M. J. Am. Chem. Soc. 1995, 117, 11584-11585.
67. (c) Garavelli, M.; Celani, P.; Bernard, F.; Robb, M. A.; Olivucci, M. J. Am. Chem. Soc. 1997, 119, 11487-11494.
68. For a recent review of polyene photophysics, see: Fuss, W.; Haas, Y.; Zilberg, S. Chem. Phys. 2000, 259, 273-295.
69. Müller, A. M.; Lochbrunner, S.; Schmid, W. E.; Füss, W. Angew. Chem., Int. Ed. 1998, 37, 505-507.
70. (a) Liu, R. S. H.; Asato, A. E. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 259-263.
71. (b) Liu, R. S. H.; Hammond, G. S. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 11153-11158.
72. (c) Liu, R. S. H. Acc. Chem. Res. 2001, 34, 555-562.
73. (a) Saltiel, J.; Metts, L.; Wrighton, M. J. Am. Chem. Soc. 1970, 92, 3227-3229.
74. (b) Saltiel, J.; D'Agostino, J. T.; Megarity, E. D.; Metts, L.; Neuberger, K. R.; Wrighton, M.; Zafiriou, O. C. Org. Photochem. 1973, 3, 1-113.
75. Srinivasan, R. J. Am. Chem. Soc. 1968, 90, 4498-4499.
76. Vanderlinden, P.; Boué, S. J. Chem. Soc. Chem. Commun. 1975, 932-933.
77. Squillacote, M. E.; Semple, T. C. J. Am. Chem. Soc. 1987, 109, 892-894.
78. (a) Dauben, W. G.; Ritscher, J. S. J. Am. Chem. Soc. 1970, 92, 2925-2926.
79. (a) Jacobs, H. J. C.; Havinga, E. Adv. Photochem. 1979, 11, 305.
80. (b) Vroegop, P. J.; Lugtenburg, J.; Havinga, E. Tetrahedron 1973, 29, 1393.
81. Nagae, H.; Kuki, M.; Zhang, J.-P.; Sashima, T.; Mukai, Y.; Koyama, Y. J. Phys. Chem. A 2000, 104, 4155-4166.
82. Siebert, T.; Schmitt, M.; Engel, V.; Materny, A.; Kiefer, W. J. Am. Chem. Soc. 2002, 124, 6242-6243.
83. Hohlneicher, G.; Dick, B. J. Photochem. 1984, 27, 215.
84. Troe, J.; Weitzel, K.-M. J. Chem. Phys. 1988, 88, 7030.