Ultrafast photodynamics of exciplex formation and photoinduced electron transfer in porphyrin-fullerene dyads linked at close proximity

Journal of Physical Chemistry A

Volumn 107, Issue 42, 2003, Pages 8834-8844

  Tkachenko, Nikolai V ^b   Lemmetyinen, Helge ^b   Sonoda, Junko ^a   Ohkubo, Kei ^a   Sato, Tomoo ^c   Imahori, Hiroshi ^d,e   Fukuzumi, Shunichi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b TAMPERE UNIVERSITY OF TECHNOLOGY   (Finland)

^c UNIVERSITY OF TSUKUBA   (Japan)

^d KYOTO UNIVERSITY   (Japan)

^e KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BAND STRUCTURE; FLUORESCENCE; FULLERENES; GROUND STATE; PORPHYRINS; PUMPING (LASER); ULTRAFAST PHENOMENA;

DYADS; PUMP PROBE TRANSIENT ABSORPTION TECHNIQUES; TIME RESOLVED ABSORPTION SPECTRAL MEASUREMENT; ULTRAFAST PHOTODYNAMICS;

ELECTRON TRANSPORT PROPERTIES;

EID: 0242406050     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp035412j     Document Type: Article

References (90)

1. (a) Marcus, R. A. Annu. Rev. Phys. Chem. 1964, 15, 155.
2. (b) Marcus, R. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1111.
3. (c) Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265.
4. (a) Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
5. (b) Mataga, N.; Miyasaka, H. Prog. React. Kinet. 1994, 19, 317.
6. (c) Gauduel, Y. J. Mol. Liq. 1995, 63, 1.
7. (d) Wynne, K.; Hochstrasser, R. M. Adv. Chem. Phys. 1999, 107, 263.
8. (e) Zhang, J. Z. J. Phys. Chem. B 2000, 104, 7239.
9. (a) Mataga, N.; Miyasaka, H. Adv. Chem. Phys. 1999, 107, 431.
10. (b) Mataga, N.; Chosrowjan, H.; Shibata, Y.; Yoshida, N.; Osuka, A.; Kikuzawa, T.; Okada, T. J. Am. Chem. Soc. 2001, 123, 12422.
11. (a) Chiorboli, C.; Rodgers, M. A. J.; Scandola, F. J. Am. Chem. Soc. 2003, 125, 483.
12. (b) Reid, G. D.; Whittaker, D. J.; Day, M. A.; Creely, C. M.; Tuite, E. M.; Kelly, J. M.; Beddard, G. S. J. Am. Chem. Soc. 2001, 123,6953.
13. (c) Kambhampati, P.; Son, D. H.; Kee, T. W.; Barbara, P. F. J. Phys. Chem. A 2000, 104, 10637.
14. Wan, C.; Fiebig, T.; Schiemann, O.; Barton, J. K.; Zewail, A. H. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 14052.
15. (b) Kononov, A. I.; Moroshkina, E. B.; Tkachenko, N. V.; Lemmetyinen, H. J. Phys. Chem. B 2001, 105, 535.
16. (c) Lewis, F. D.; Wu, T.; Liu, X.; Letsinger, R. L.; Greenfield, S. R.; Miller, S. E.; Wasielewski, M. R. J. Am. Chem. Soc. 2000, 122, 2889.
17. (a) Asbury, J. B.; Ghosh, H. N.; Ellingson, R. J.; Ferrere, S.; Nozik, A. J.; Lian, T. Ultrafast Phenomena XI; Springer Series in Chemical Physics; Springer: Berlin, Germany, 1998; p 639.
18. (b) Asbury, J. B.; Hao, E.; Wang, Y.; Ghosh, H. N.; Lian, T. J. Phys. Chem. B 2001, 105, 4545.
19. (c) Zimmermann, C.; Willig, F.; Ramakrishna, S.; Burfeindt, B.; Pettinger, B.; Eichberger, R.; Storch, W. J. Phys. Chem. B 2001, 105, 9245.
20. Kaim, W.; Schwederski, B. Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life; Wiley: Chichester, U.K., 1994.
21. (a) Paddon-Row, M. N. Acc. Chem. Res. 1994. 27, 18.
22. (b) Jordan, K. D.; Paddon-Row, M. N. Chem. Rev. 1992, 92, 395.
23. (c) Paddon-Row, M. N. In Electron Transfer in Chemistry; Balzani, Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 3, pp 179-271.
24. Wasielewski, M. R. In Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part A, pp 161-206.
25. (b) Wasielewski, M. R. Chem. Rev. 1992, 92, 435.
26. (c) Wasielewski, M. R.; Wiederrecht, G. P.; Svec, W. A.; Niemczyk, M. P. Sol. Energy Mater. Sol. Cells 1995, 38, 127.
27. Verhoeven, J. W. Adv. Chem. Phys. 1999, 106, 603.
28. (a) Osuka, A.; Mataga, N.; Okada, T. Pure Appl. Chem. 1997, 69, 797.
29. (b) Sun, L.; Hammarström, L.; Åkermak, B.; Styring, S. Chem. Soc. Rev. 2001, 30, 36.
30. (c) Scandola, F.; Chiorboli, C.; Indelli, M. T.; Rampi, M. A. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 3, pp 337-408.
31. (a) Harriman, A.; Sauvage, J.-P. Chem. Soc. Rev. 1996, 25, 41.
32. (b) Blanco, M.-J.; Jiménez, M. C.; Chambron, J.-C.; Heitz,. V.; Linke, M.; Sauvage, J.-P. Chem. Soc. Rev. 1999, 28, 293.
33. (c) Chambron, J. C.; Collin, J. P.; Dalbavie, J. O.; Dietrich-Buchecker, C. O.; Heitz, V.; Odobel, F.; Solladie, N.; Sauvage, J. P. Coord. Chem. Rev. 1998, 180, 1299.
34. (a) Lewis, F. D.; Liu, X. Y.; Liu, J. O.; Miller, S. E.; Wasielewski, M. R. Nature 2000, 406, 51.
35. (b) Lewis, F. D.; Letsinger, R. L.; Wasielewski, M. R. Acc. Chem. Res. 2001, 34, 159.
36. (a) Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537.
37. (b) Imahori, H.; Sakata, Y. Eur. J. Org. Chem. 1999, 64, 2445.
38. (c) Fukuzumi, S.; Imahori, H. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 927-975.
39. (d) Imahori, H.; Mori, Y.; Matano, Y. Photochem. Photobiol. C 2003, 4, 51.
40. (a) Gust, D.; Moore, T. A. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 8, pp 153-190.
41. (b) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40.
42. (c) Gust, D.; Moore, T. A.; Moore, A. L. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 3, pp 272-336.
43. (a) Imahori, H.; Yamada, K.; Hasegawa, M.; Taniguchi, S.; Okada, T.; Sakata, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2626.
44. (b) Imahori, H.; Tamaki, K.; Guldi, D. M.; Luo, C.; Fujitsuka, M.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 2607.
45. (c) Fukuzumi, S.; Imahori, H.; Yamada, H.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O.; Guldi, D. M. J. Am. Chem. Soc. 2001, 123, 2571.
46. Imahori, H.; Guldi, D. M.; Tamaki, K.; Yoshida, Y.; Luo, C.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 6617.
47. Fukuzumi, S. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 8, pp 115-151.
48. (a) Fukuzumi, S.; Guldi, D. M. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 270-337.
49. (b) Guldi, D. M. Chem. Soc. Rev. 2002, 31, 22.
50. Eberson, L. Electron-Transfer Reactions in Organic Chemistry; Reactivity and Structure; Springer: Heidelberg, Germany, 1987; Vol. 25.
51. Imahori, H.; Tkachenko, N. V.; Vehmanen, V.; Tamaki, K.; Lemmetyinen, H.; Sakata, Y.; Fukuzumi, S. J. Phys. Chem. A 2001, 105, 1750.
52. Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771.
53. Gould, I. R.; Farid, S. Acc. Chem. Res. 1996, 29, 522.
54. (a) Hilinski, E. F.; Masnovi, J. M.; Amatore, C.; Kochi, J. K.; Rentzepis, P. M. J. Am. Chem. Soc. 1983, 105, 6167.
55. (b) Hilinski, E. F.; Masnovi, J. M.; Kochi, J. K.; Rentzepis, P. M. J. Am. Chem. Soc. 1984, 106, 8071.
56. (a) Hubig, S. M.; Bockman, T. M.; Kochi, J. K. J. Am. Chem. Soc. 1996, 118, 3842.
57. (b) Hubig, S. M.; Bockman, T. M.; Kochi, J. K. J. Am. Chem. Soc. 1997, 119, 2926.
58. (c) Rathore, R.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1997, 119, 11468.
59. (d) Bockman, T. M.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 6542.
60. (e) Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1999, 121, 1688.
61. (a) Ojima, S.; Miyasaka, H.; Mataga, N. J. Phys. Chem. 1990, 94, 4147, 5834, 7534.
62. (b) Asahi, T.; Ohkohchi, M.; Mataga, N. J. Phys. Chem. 1993, 97, 13132.
63. (c) Asahi, T.; Mataga, N. J. Phys. Chem. 1991, 95, 1956.
64. Kesti, T. J.; Tkachenko, N. V.; Vehmanen, V.; Yamada, H.; Imamori, H.; Fukuzumi, S.; Lemmetyinen, H. J. Am. Chem. Soc. 2002, 124, 8067.
65. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R., Purification of Laboratory Chemicals, 4th ed.; Pergamon Press: Elmsford, NY, 1996.
66. Imahori, H.; Tamaki, K.; Araki, Y.; Sekiguchi, Y.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2002, 124, 5165.
67. Imahori, H.; Ozawa, S.; Ushida, K.; Takahashi, M.; Azuma, T.; Ajavakom, A.; Akiyama, T.; Hasegawa, M.; Taniguchi, S.; Okada, T.; Sakata, Y. Bull. Chem. Soc. Jpn. 1999, 72, 485.'
68. Takagi, S.; Miyamoto, T. K.; Sakai, Y. Bull. Chem. Soc. Jpn. 1986, 59, 2371.
69. (a) Tkachenko, N. V.; Tauber, A. Y.; Grandell, D.; Hynninen, P. H.; Lemmetyinen, H. J. Phys. Chem. A 1999, 103, 3646.
70. (b) Tkachenko, N. V.; Rantala, L.; Tauber, A. Y.; Helaja, J.; Hynninen, P. H.; Lemmetyinen, H. J. Am. Chem. Soc. 1999, 121, 9378.
71. Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Nonaqueous Systems; Marcel Dekker: New York, 1990.
72. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209, 221.
73. Fuhrhop, J.-H.; Mauzerall, D. J. Am. Chem. Soc. 1969, 91, 4174.
74. Luo, C.; Guldi, D. M.; Imahori, H.; Tamaki, K.; Sakata, Y. J. Am. Chem. Soc. 2000, 122, 6535.
75. (a) Akimoto, S.; Yamazaki, T.; Yamazaki, I.; Osuka, A. Chem. Phys. Lett. 1999, 309, 177.
76. (b) Nakano, A.; Yasuda, Y.; Yamazaki, T.; Akimoto, S.; Yamazaki, I.; Miyasaka, H.; Itaya, A.; Murakami, M.; Osuka, A. J. Phys. Chem. A 2001, 105, 4822.
77. (a) Andersson, M.; Davidsson, J.; Hammarström, L.; Korppi-Tomola, J.; Peltola, T. J. Phys. Chem. B 1999, 103, 3258.
78. (b) Harriman, A.; Hissler, M.; Trompette, O.; Ziessel, R. J. Am. Chem. Soc. 1999, 121, 2516.
79. Kesti, T.; Tkachenko, N.; Yamada, H.; Imahori, H.; Fukuzumi, S.; Lemmetyinen, H. Photochem. Photobiol. Sci. 2003, 2, 251.
80. The maximum bleaching of the porphyrin ground-state absorption is achieved at 5-15 ps delay time (Figure 6). Also the 4.3 ps component (Figure 6) has a sharp band at 560 nm, which allows associating it with Q-band bleaching. Therefore, this component, 4.3 ps, can be attributed to formation of the exciplex from fullerene singlet excited state. Noticeably, this relaxation channel gives only minor absorption increase in PhCN. In toluene, its contribution is even less visible giving no observable signal increase at the same wavelengths.
81. The extinction of the CT band is roughly 1000 times lower than that of the Soret band, which is right at the excitation wavelength. It is hardly possible to achieve any sensible amount of directly excited CT. On the other hand, relaxation of the second excited state to exciplex is an extremely fast reaction and will be observed as almost instant formation of the exciplex.
82. (a) Fukuzumi, S.; Suenobu, T.; Patz, M.; Hirasaka, T.; Itoh, S.; Fujitsuka, M.; Ito, O. J. Am. Chem. Soc. 1998, 120, 8060.
83. (b) Fuzuzumi, S.; Suenobu, T.; Hirasaka, T.; Sakurada, N.; Arakawa, R.; Fujitsuka, M.; Ito, O. J. Phys. Chem. A 1999, 103, 5935.
84. Imahori, H.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Phys. Chem. A 2001, 105, 325.
85. (a) Kadish, K. M.; Gao, X.; Van Caemelbecke, E.; Suenobu, T.; Fukuzumi, S. J. Phys. Chem. A 2000, 104, 3878.
86. (b) Guldi, D. M.; Asmus, K.-D. J. Phys. Chem. A 1997, 101, 1472.
87. (c) Guldi, D. M.; Hungerbühler, H.; Asmus, K.-D. J. Phys. Chem. 1995, 99, 9380.
88. The third important parameter is the mutual orientation of the reactant. However, the molecular modeling (Figure 3) indicates only slight and unregular variation in the orientation factor for this series of the dyad whereas the distance changes from almost van der Waals contact to 5.2 Å (edge-to-edge).
89. The molecular modeling was performed for free base dyads, Figure 3. However, one can expect a similar relation in center-to-center distances for the Zn dyads.
90. 60 can be regarded as the charge-separated state with a strong interaction. However, the exact difference between they are clearly differentiated by their transient absorption spectra as shown in this study.