Dynamics of Bimolecular Photoinduced Electron-Transfer Reactions

Accounts of Chemical Research

Volumn 29, Issue 11, 1996, Pages 522-528

  Gould, Ian R ^a,b,c   Farid, Samir ^a,d,e,f  

^a EASTMAN KODAK COMPANY   (United States)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

^c Och Spine at New York Presbyterian Hospitals

^d AIN SHAMS UNIVERSITY   (Egypt)

^e UNIVERSITY OF GÖTTINGEN   (Germany)

^f MAX PLANCK INSTITUTE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001711325     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar950053z     Document Type: Article

References (88)

1. (a) Advances in Electron Transfer Chemistry; Mariano, P. S., Ed.; Jai Press: Greenwich, CT, 1991-1994; Vols. 1-4.
2. (b) Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988.
3. (c) Kavarnos, G. J.; Turro, N. J. Chem. Rev. 1986, 86, 401.
4. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259.
5. (a) Weller, A. Z. Phys. Chem. (Munich) 1982, 130, 129.
6. (b) Mataga, N. Pure Appi Chem. 1984, 56, 1255.
7. Being a second-order process, return electron transfer in the separated radical ions is much slower than in the geminate pair.
8. For a review see: Mattes, S. L.; Farid, S. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1983; Vol. 6, p 233.
9. The data points in Figure 1 are from the following: (a) Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1983, 105, 1386. (b) Mattes, S. L.; Farid, S. Unpublished results. (c) Farid, S.; Hartman, S. E.; Evans T. R. In The Exciplex; Gordon, M., Ware, W. R., Eds.; Academic Press: New York, 1975; p 327. (d) Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R.; Todd, W. P.; Mattes, S. L. J. Am. Chem. Soc. 1989, 111, 8973. (e) Mattes, S. L.; Farid, S. J. Chem. Soc., Chem. Commun. 1980, 457.
10. The data points in Figure 1 are from the following: (a) Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1983, 105, 1386. (b) Mattes, S. L.; Farid, S. Unpublished results. (c) Farid, S.; Hartman, S. E.; Evans T. R. In The Exciplex; Gordon, M., Ware, W. R., Eds.; Academic Press: New York, 1975; p 327. (d) Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R.; Todd, W. P.; Mattes, S. L. J. Am. Chem. Soc. 1989, 111, 8973. (e) Mattes, S. L.; Farid, S. J. Chem. Soc., Chem. Commun. 1980, 457.
11. The data points in Figure 1 are from the following: (a) Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1983, 105, 1386. (b) Mattes, S. L.; Farid, S. Unpublished results. (c) Farid, S.; Hartman, S. E.; Evans T. R. In The Exciplex; Gordon, M., Ware, W. R., Eds.; Academic Press: New York, 1975; p 327. (d) Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R.; Todd, W. P.; Mattes, S. L. J. Am. Chem. Soc. 1989, 111, 8973. (e) Mattes, S. L.; Farid, S. J. Chem. Soc., Chem. Commun. 1980, 457.
12. The data points in Figure 1 are from the following: (a) Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1983, 105, 1386. (b) Mattes, S. L.; Farid, S. Unpublished results. (c) Farid, S.; Hartman, S. E.; Evans T. R. In The Exciplex; Gordon, M., Ware, W. R., Eds.; Academic Press: New York, 1975; p 327. (d) Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R.; Todd, W. P.; Mattes, S. L. J. Am. Chem. Soc. 1989, 111, 8973. (e) Mattes, S. L.; Farid, S. J. Chem. Soc., Chem. Commun. 1980, 457.
13. The data points in Figure 1 are from the following: (a) Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1983, 105, 1386. (b) Mattes, S. L.; Farid, S. Unpublished results. (c) Farid, S.; Hartman, S. E.; Evans T. R. In The Exciplex; Gordon, M., Ware, W. R., Eds.; Academic Press: New York, 1975; p 327. (d) Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R.; Todd, W. P.; Mattes, S. L. J. Am. Chem. Soc. 1989, 111, 8973. (e) Mattes, S. L.; Farid, S. J. Chem. Soc., Chem. Commun. 1980, 457.
14. This effect was described in ref 5, p 305, ref 6a, and Mattes, S. L.; Farid, S. Science 1984, 226, 917.
15. Marcus, R. A. J. Chem. Phys. 1956, 24, 966.
16. (a) Beitz, J. V.; Miller, J. R. J. Chem. Phys. 1979, 71, 4579.
17. (b) Miller, J. R.; Beitz, J. V.; Huddleston, R. K. J. Am. Chem. Soc. 1984, 106, 5057.
18. See for example: Eberson, L. In Advances in Physical Organic Chemistry; Gold, V., Bethell, D., Eds.; Academic Press: London, 1982; Vol. 18, p 79.
19. (a) Miller, J. R.; Calcaterra, L. T.; Closs, G. L. J. Am. Chem. Soc. 1984, 106, 3047.
20. (b) Closs, G. L.; Miller, J. R. Science 1988, 240, 440.
21. (a) Van Duyne, R. P.; Fischer, S. F. Chem. Phys. 1974, 5, 183.
22. (b) Ulstrup, J.; Jortner, J. J. Chem. Phys. 1975, 63, 4358.
23. (c) Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265.
24. 13b-e
25. (b) Walker, G. C.; Barbara, P. F.; Doom, S. K.; Dong, Y.; Hupp. J. T. J. Phys. Chem. 1991, 95, 5712.
26. (c) Markel, F.; Ferris, N. S.; Gould, I. R.; Myers, A. B. J. Am. Chem. Soc. 1992, 114, 6208.
27. (d) Doom, S. K.; Dyer, R. B.; Stoutland, P. O.; Woodruff, W. H. J. Am. Chem. Soc. 1993, 115, 6398.
28. (e) Kulinowski, K.; Gould, I. R., Myers, A. B. J. Phys. Chem. 1995, 99, 9017.
29. Gould, I. R.; Ege, D.; Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1987, 109, 3794.
30. 16
31. (b) Gould, I. R.; Farid, S. J. Am. Chem. Soc. 1993, 115, 4814.
32. Gould, I. R.; Ege, D.; Moser, J. E.; Farid, S. J. Am. Chem. Soc. 1990, 112, 4290.
33. 17b
34. (b) Lewis, F. D.; Bedell, A. M.; Dykstra, R. E.; Elbert, J. E.; Gould, I. R.; Farid, S. J. Am. Chem. Soc. 1990, 112, 8055.
35. (a) Beens, H.; Weller, A. In Organic Molecular Photophysics; Birks, J. B., Ed.; Wiley: London, 1975; Vol. 2, Chapter 4.
36. (b) Mataga, N. In Photochemical Processes in Organized Molecular Systems; Honda, K., Ed.; Elsevier: New York, 1991; p 3.
37. Gould, I. R.; Young, R. H.; Farid, S. In Photochemical Processes in Organized Molecular Systems; Honda, K., Ed.; Elsevier: New York, 1991; p 19.
38. 20b
39. (b) Murphy, S.; Yang, X.; Schuster, G. B. J. Org. Chem. 1995, 60, 2411.
40. (a) Weller, A. In The Exciplex; Gordon, M.; Ware, W. R., Eds.; Academic Press: New York, 1975, p 23.
41. (b) Mataga, N.; Ottolenghi, M. In Molecular Association; Foster, R., Ed.; Academic Press: New York, 1979; Vol. 2, p 1.
42. (c) Jones, G., III. In Photoinduced Electron Transfer. Part A. Conceptual Basis; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; p 245.
43. Gould, I. R.; Young, R. H.; Moody, R. E.; Fand, S. J. Phys. Chem. 1991, 95, 2068.
44. Gould, I. R.; Moody, R.; Farid, S, J. Am. Chem. Soc. 1988, 110, 7242.
45. Gould, I. R.; Farid, S.; Young, R. H. J. Photochem. Photobiol., A 1992, 65, 133.
46. Marcus, R. A. J. Phys. Chem. 1984, 81, 4494.
47. (a) Gould, I. R.; Noukakis, D.;Goodman, J. L.; Young, R. H.; Farid, S. J. Am. Chem. Soc. 1993, 115, 3830.
48. (b) Gould, I. R.; Noukakis, D.; Gomez-Jahn, L.; Goodman, J. L.; Farid, S. J. Am. Chem. Soc. 1993, 115, 4405.
49. Gould, I. R.; Noukakis, D.; Gomez-Jahn, L.; Young, R. H.; Goodman, J. L.; Farid, S. Chem. Phys. 1993, 176, 439.
50. 28b
51. (b) Zeng, Y.; Zimmt, M. B. J. Phys. Chem. 1992, 96, 8395.
52. Oliver, A. M.; Paddon-Row, M. N.; Kroon, J.; Verhoeven, J. W. Chem. Phys. Lett. 1992, 197, 371.
53. 30b,c
54. (b) Caspar, J. V.; Meyer, T. J. J. Phys. Chem. 1983, 87, 952.
55. (c) Barqawi, K. R.; Murtaza, Z.; Meyer, T. J. J. Phys. Chem. 1991, 95, 47.
56. (a) Examples of spectra and some preliminary analyses are described in ref 31b.
57. (b) Gould, I. R.; Fand, S. J. Phys. Chem. 1992, 96, 7635.
58. For a review, see: Wasielewski, M. R. Chem. Rev. 1992, 92, 435.
59. See, for example: (a) Mataga, N.; Okada, T.; Kanda, Y.; Shioyama, H. Tetrahedron 1986, 42, 6143, (b) Mataga, N.; Asahi, T.; Kanda, Y.; Okada, T.; Kakitani, T. Chem. Phys. 1988, 127, 249. (c) Vauthey, E.; Suppan, P.; Haselbach, E. Helv. Chim. Acta 1988, 71, 93. (d) Levin, P. P.; Pluzhnikov, P. F.; Kuzmin, V. A. Chem. Phys. Lett. 1988, 147, 283. (e) Kikuchi, K.; Takahashi, Y.; Koike, K.; Wakamatsu, K.; Ikeda, H.; Miyaehi, T. Z. Phys. Chem. (Munich) 1990, 167, 27. (f) Lewitzka, F.; Löhmannsröben, H.-G. Z. Phys. Chem. (Munich) 1990, 169, 203.
60. See, for example: (a) Mataga, N.; Okada, T.; Kanda, Y.; Shioyama, H. Tetrahedron 1986, 42, 6143, (b) Mataga, N.; Asahi, T.; Kanda, Y.; Okada, T.; Kakitani, T. Chem. Phys. 1988, 127, 249. (c) Vauthey, E.; Suppan, P.; Haselbach, E. Helv. Chim. Acta 1988, 71, 93. (d) Levin, P. P.; Pluzhnikov, P. F.; Kuzmin, V. A. Chem. Phys. Lett. 1988, 147, 283. (e) Kikuchi, K.; Takahashi, Y.; Koike, K.; Wakamatsu, K.; Ikeda, H.; Miyaehi, T. Z. Phys. Chem. (Munich) 1990, 167, 27. (f) Lewitzka, F.; Löhmannsröben, H.-G. Z. Phys. Chem. (Munich) 1990, 169, 203.
61. See, for example: (a) Mataga, N.; Okada, T.; Kanda, Y.; Shioyama, H. Tetrahedron 1986, 42, 6143, (b) Mataga, N.; Asahi, T.; Kanda, Y.; Okada, T.; Kakitani, T. Chem. Phys. 1988, 127, 249. (c) Vauthey, E.; Suppan, P.; Haselbach, E. Helv. Chim. Acta 1988, 71, 93. (d) Levin, P. P.; Pluzhnikov, P. F.; Kuzmin, V. A. Chem. Phys. Lett. 1988, 147, 283. (e) Kikuchi, K.; Takahashi, Y.; Koike, K.; Wakamatsu, K.; Ikeda, H.; Miyaehi, T. Z. Phys. Chem. (Munich) 1990, 167, 27. (f) Lewitzka, F.; Löhmannsröben, H.-G. Z. Phys. Chem. (Munich) 1990, 169, 203.
62. See, for example: (a) Mataga, N.; Okada, T.; Kanda, Y.; Shioyama, H. Tetrahedron 1986, 42, 6143, (b) Mataga, N.; Asahi, T.; Kanda, Y.; Okada, T.; Kakitani, T. Chem. Phys. 1988, 127, 249. (c) Vauthey, E.; Suppan, P.; Haselbach, E. Helv. Chim. Acta 1988, 71, 93. (d) Levin, P. P.; Pluzhnikov, P. F.; Kuzmin, V. A. Chem. Phys. Lett. 1988, 147, 283. (e) Kikuchi, K.; Takahashi, Y.; Koike, K.; Wakamatsu, K.; Ikeda, H.; Miyaehi, T. Z. Phys. Chem. (Munich) 1990, 167, 27. (f) Lewitzka, F.; Löhmannsröben, H.-G. Z. Phys. Chem. (Munich) 1990, 169, 203.
63. See, for example: (a) Mataga, N.; Okada, T.; Kanda, Y.; Shioyama, H. Tetrahedron 1986, 42, 6143, (b) Mataga, N.; Asahi, T.; Kanda, Y.; Okada, T.; Kakitani, T. Chem. Phys. 1988, 127, 249. (c) Vauthey, E.; Suppan, P.; Haselbach, E. Helv. Chim. Acta 1988, 71, 93. (d) Levin, P. P.; Pluzhnikov, P. F.; Kuzmin, V. A. Chem. Phys. Lett. 1988, 147, 283. (e) Kikuchi, K.; Takahashi, Y.; Koike, K.; Wakamatsu, K.; Ikeda, H.; Miyaehi, T. Z. Phys. Chem. (Munich) 1990, 167, 27. (f) Lewitzka, F.; Löhmannsröben, H.-G. Z. Phys. Chem. (Munich) 1990, 169, 203.
64. See, for example: (a) Mataga, N.; Okada, T.; Kanda, Y.; Shioyama, H. Tetrahedron 1986, 42, 6143, (b) Mataga, N.; Asahi, T.; Kanda, Y.; Okada, T.; Kakitani, T. Chem. Phys. 1988, 127, 249. (c) Vauthey, E.; Suppan, P.; Haselbach, E. Helv. Chim. Acta 1988, 71, 93. (d) Levin, P. P.; Pluzhnikov, P. F.; Kuzmin, V. A. Chem. Phys. Lett. 1988, 147, 283. (e) Kikuchi, K.; Takahashi, Y.; Koike, K.; Wakamatsu, K.; Ikeda, H.; Miyaehi, T. Z. Phys. Chem. (Munich) 1990, 167, 27. (f) Lewitzka, F.; Löhmannsröben, H.-G. Z. Phys. Chem. (Munich) 1990, 169, 203.
65. (a) Gould, I. R.; Moser, J. E.; Ege, D.; Farid, S. J. Am. Chem. Soc. 1988, 110, 1991.
66. (b) Gould, I. R.; Farid. S. J. Am. Chem. Soc. 1988, 110, 7883.
67. (c) Gould, I. R.; Farid, S. J. Phys. Chem. 1993, 97, 13067.
68. (d) Chung, W.-S.; Turro, N. J.; Gould, I. R.; Farid, S. J. Phys. Chem. 1991, 95, 7752.
69. (e) Gould, I. R.; Moser, J. E.; Armitage, B.; Farid, S.; Goodman, J. L.; Herman, M. S. J. Am. Chem. Soc. 1980, 111, 1917.
70. (a) Knibbe, H.; Röllig, K.; Schäfer, F. P.; Weller, A. J. Chem. Phys. 1967, 47, 1184.
71. (b) Mataga, N.; Murata, Y. J. Am. Chem. Soc. 1969, 91, 3144.
72. (a) Gould, I. R.; Mueller, J. L.; Farid, S. Z. Phys. Chem. (Munich) 1991, 170, 143.
73. (b) Gould, I. R.; Young, R. H.; Mueller, L. J.; Farid, S. J. Am. Chem. Soc. 1994, 116, 8176.
74. 37b-d
75. (b) Rau, H.; Frank, R.; Greiner, G. J. Phys. Chem. 1986, 90, 2476.
76. (c) Stevens, B.; Biver, C. J.; McKeithan, D. N. Chem. Phys. Lett. 1991, 187, 590.
77. (d) Kikuchi, K.; Takahashi, Y.; Katagiri, T.; Niwa, T.; Hoshi, M.; Miyaahi, T. Chem. Phys. Lett. 1991, 180, 403.
78. 38b
79. (b) Gould, I. R.; Young, R. H.; Mueller, L. J.; Albrecht, A. C.; Farid, S. J. Am. Chem. Soc. 1994, 116, 8188.
80. -solv). See ref 36b for further discussion.
81. For a review, see: Peters, K. S. In Advances in Electron Transfer Chemistry; Mariano, P. S., Ed.; Jai Press: Greenwich, CT, 1994; Vol. 4, p 27.
82. Arnold, B. R.; Noukakis, D.; Farid, S.; Goodman, J. L.; Gould, I. R. J. Am. Chem. Soc. 1995, 117, 4399.
83. Arnold, B. R.; Farid, S.; Goodman, J. L.; Gould, I. R. J. Am. Chem. Soc., 1996, 118, 5482.
84. 43b
85. (b) Peters, K. S.; Li, B. J. Phys. Chem. 1994, 98, 401.
86. Weller, A. Z. Phys. Chem. (Munich) 1982, 133, 93.
87. (a) Gould, I. R.; Moser, J. E.; Armitage, B.; Fand, S. Res. Chem. Intermed. 1995, 21, 793.
88. (b) Todd, W. P.; Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R. J. Am. Chem. Soc. 1991, 113, 3601.