Porphyrin-fullerene linked systems as artificial photosynthetic mimics

Organic and Biomolecular Chemistry

Volumn 2, Issue 10, 2004, Pages 1425-1433

  Imahori, Hiroshi ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROPHYLL; COMPLEXATION; ELECTRON IRRADIATION; ENERGY TRANSFER; FULLERENES; LIGHT POLARIZATION; ORGANIC SOLVENTS; PHOTOCATALYSIS; PHOTOSYNTHESIS; PORPHYRINS; PROTEINS; QUANTUM EFFICIENCY; REACTION KINETICS;

ARTIFICIAL PHOTOSYNTHETIC MIMICS; CHARGE SHIFT; ELECTRON TRANSFER (ET); LINKED SYSTEMS;

MOLECULAR BIOLOGY;

BACTERIA (MICROORGANISMS);

FERROCENE; FERROUS ION; FULLERENE DERIVATIVE; METALLOPORPHYRIN; POLYMER; PORPHYRIN; ZINC;

ALGORITHM; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; ENERGY METABOLISM; ENERGY RESOURCE; ENERGY TRANSFER; NANOTECHNOLOGY; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; PHOTOSYNTHESIS; REVIEW; SOLAR ENERGY;

ALGORITHMS; ELECTRONS; ENERGY METABOLISM; ENERGY TRANSFER; ENERGY-GENERATING RESOURCES; FERROUS COMPOUNDS; FULLERENES; METALLOPORPHYRINS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NANOTECHNOLOGY; OXIDATION-REDUCTION; PHOTOCHEMISTRY; PHOTOSYNTHESIS; POLYMERS; PORPHYRINS; SOLAR ENERGY; ZINC;

EID: 2942670310     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b403024a     Document Type: Review

References (118)

1. (a) Molecular Devices and Machines, ed. V. Balzani, M. Venturi and A. Credi, Wiley-VCH, Weinheim, 2003;
2. (b) Electron Transfer in Chemistry, ed. V. Balzani, Wiley-VCH, Weinheim, 2001;
3. (c) Electron Transfer, ed. J. Jortner and M. Bixon, John Wiley & Sons, New York, 1999, part 1 and 2;
4. (d) Molecular Electronics, ed. J. Jortner and M. Ratner, Blackwell Science, Oxford, 1997;
5. (e) Organic Photovoltaics, ed. C. Brabec, V. Dyakonov, J. Parisi and N. S. Sariciftci, Springer, Berlin, 2003;
6. (f) K. Domen, J. N. Kondo, H. Hara and T. Takata, Bull. Chem. Soc. Jpn., 2000, 73, 1307.
7. (a) The Photosynthetic Reaction Center, ed. J. Deisenhofer and J. R. Norris, Academic Press, San Diego, 1993;
8. (b) Anoxygenic Photosynthetic Bacteria, ed. R. E. Blankenship, M. T. Madigan and C. E. Bauer, Kluwer Academic Publishing, Dordrecht, 1995;
9. (c) P. A. Loach, Photochem. Photobiol., 1997, 65S, 134S.
10. (a) G. McDermott, S. M. Prince, A. A. Freer, A. M. Hawthornthwaite- Lawless, M. Z. Papiz, R. J. Cogdell and N. W. Isaacs, Nature, 1995, 374, 517;
11. (b) J. M. Olson, Photochem. Photobiol., 1998, 67, 61;
12. (c) A. Zouni, H.-T. Witt, J. Kern, P. Fromme, N. Kraub, W. Saenger and P. Orth, Nature, 2001, 409, 739;
13. (d) P. Jordan, P. Fromme, H.-T. Witt, O. Klukas, W. Saenger and N. Kraub, Nature, 2001, 411, 909.
14. (a) M. R. Wasielewski, Chem. Rev., 1992, 92, 435;
15. (b) D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198;
16. (c) D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 2001, 34, 40;
17. (d) D. Holten, D. F. Bocian and J. S. Lindsey, Acc. Chem. Res., 2002, 35, 57;
18. (e) D. M. Adams, L. Brus, E. D. Chidsey, S. Creager, C. Creutz, C. R. Kagan, P. V. Kamat, M. Lieberman, J. S. Lindsey, R. A. Marcus, R. M. Metzger, M. E. Michel-Beyerle, J. R. Miller, M. D. Newton, D. R. Rolison, O. Sankey, K. S. Schanze, J. Yardley and X. Zhu, J. Phys. Chem. B, 2003, 107, 6668.
19. (a) H. Kurreck and M. Huber, Angew. Chem., Int. Ed. Engl., 1995, 34, 849;
20. (b) A. Harriman and J.-P. Sauvage, Chem. Soc. Rev., 1996, 26, 41;
21. (c) J. W. Verhoeven, Adv. Chem. Phys., 1999, 106, 603;
22. (d) L. Sun, L. Hammarström, B. Åkermark and S. Styring, Chem. Soc. Rev., 2001, 30, 36;
23. (e) D. M. Guldi and M. Prato, Acc. Chem. Res., 2000, 33, 695;
24. (f) N. Armaroli, Photochem. Photobiol. Sci., 2003, 2, 73.
25. (a) M. N. Paddon-Row, Acc. Chem. Res., 1994, 27, 18;
26. (b)K. Maruyama, A. Osuka and N. Mataga, Pure Appl. Chem., 1994, 66, 867.
27. (a) H. Imahori and Y. Sakata, Adv. Mater., 1997, 9, 537;
28. (b) H. Imahori and Y. Sakata, Eur. J. Org. Chem., 1999, 2445;
29. (c) H. Imahori and S. Fukuzumi, Adv. Mater., 2001, 13, 1197;
30. (d) H. Imahori, Y. Mori and Y. Matano, J. Photochem. Photobiol., C, 2003, 4, 51;
31. (e) H. Imahori and S. Fukuzumi, Adv. Funct. Mater., 2004, 14, in press;
32. (f) H. Imahori, J. Phys. Chem. B, 2004, 108, in press.
33. (a) R. A. Marcus, Annu. Rev. Phys. Chem., 1964, 15, 155;
34. (b) R. A. Marcus and N. Sutin, Biochim. Biophys. Acta, 1985, 811, 265;
35. (c) R. A. Marcus, Angew. Chem., Int. Ed. Engl., 1993, 32, 1111.
36. The Porphyrin Handbook, ed. K. M. Kadish, K. Smith and R. Guilard, Academic Press, San Diego, CA, 2000.
37. (a) Science of Fullerenes and Carbon Nanotubes, ed. M. S. Dresselhaus, G. Dresselhaus and P. C. Eklund, Academic Press, San Diego, 1995;
38. (b) Fullerenes, ed. K. M. Kadish and R. S. Ruoff, John Wiley & Sons, New York, 2000.
39. (a) H. Imahori, K. Hagiwara, M. Aoki, T. Akiyama, S. Taniguchi, T. Okada, M. Shirakawa and Y. Sakata, Chem. Phys. Lett., 1996, 263, 545;
40. (b) N. V. Tkachenko, C. Guenther, H. Imahori, K. Tamaki, Y. Sakata, H. Lemmetyinen and S. Fukuzumi, Chem. Phys. Lett., 2000, 326, 344;
41. (c) H. Imahori, N. V. Tkachenko, V. Vehmanen, K. Tamaki, H. Lemmetyinen, Y. Sakata and S. Fukuzumi, J. Phys. Chem. A, 2001, 105, 1750;
42. (d) V. Vehmanen, N. V. Tkachenko, H. Imahori, S. Fukuzumi and H. Lemmetyinen, Spectrochim. Acta, Part A, 2001, 57, 2229;
43. (e) H. Imahori, H. Yamada, D. M. Guldi, Y. Endo, A. Shimomura, S. Kundu, K. Yamada, T. Okada, Y. Sakata and S. Fukuzumi, Angew. Chem., Int. Ed., 2002, 41, 2344.
44. S. Fukuzumi, K. Ohkubo, H. Imahori and D. M. Dirk, Chem. Eur. J., 2003, 9, 1585.
45. H. Imahori, K. Hagiwara, T. Akiyama, S. Taniguchi, T. Okada and Y. Sakata, Chem. Lett., 1995, 265.
46. H. Imahori, K. Hagiwara, M. Aoki, T. Akiyama, S. Taniguchi, T. Okada, M. Shirakawa and Y. Sakata, J. Am. Chem. Soc., 1996, 118, 11771.
47. H. Imahori and Y. Sakata, Chem. Lett., 1996, 199.
48. K. Yamada, H. Imahori, Y. Nishimura, I. Yamazaki and Y. Sakata, Chem. Lett., 1999, 895.
49. H. Imahori, S. Ozawa, K. Ushida, M. Takahashi, T. Azuma, A. Ajavakom, T. Akiyama, M. Hasegawa, S. Taniguchi, T. Okada and Y. Sakata, Bull Chem. Soc. Jpn., 1999, 72, 485.
50. H. Imahori, K. Tamaki, H. Yamada, K. Yamada, Y. Sakata, Y. Nishimura, I. Yamazaki, M. Fujitsuka and O. Ito, Carbon, 2000, 38, 1599.
51. C. Luo, D. M. Guldi, H. Imahori, K. Tamaki and Y. Sakata, J. Am. Chem. Soc., 2000, 122, 6535.
52. H. Imahori, M. E. El-Khouly, M. Fujitsuka, O. Ito, Y. Sakata and S. Fukuzumi, J. Phys. Chem. A, 2001, 105, 325.
53. S. Fukuzumi, H. Imahori, H. Yamada, M. E. El-Khouly, M. Fujitsuka, O. Ito and D. M. Guldi, J. Am. Chem. Soc., 2001, 123, 2571.
54. H. Imahori, K. Tamaki, D. M. Guldi, C. Luo, M. Fujitsuka, O. Ito, Y. Sakata and S. Fukuzumi, J. Am. Chem. Soc., 2001, 123, 2607.
55. H. Imahori, T. Hasobe, H. Yamada, P. V. Kamat, S. Barazzouk, M. Fujitsuka, O. Ito and S. Fukuzumi, Chem. Lett., 2001, 784.
56. S. Fukuzumi, K. Ohkubo, H. Imahori, J. Shao, Z. Ou, G. Zheng, Y. Chen, R. K. Pandey, M. Fujitsuka, O. Ito and K. M. Kadish, J. Am. Chem. Soc., 2001, 123, 10676.
57. K. Ohkubo, H. Imahori, J. Shao, Z. Ou, K. M. Kadish, Y. Chen, G. Zheng, R. K. Pandey, M. Fujitsuka, O. Ito and S. Fukuzumi, J. Phys. Chem. A, 2002, 106, 10991.
58. T. J. Kesti, N. V. Tkachenko, V. Vehmanen, H. Yamada, H. Imahori, S. Fukuzumi and H. Lemmetyinen, J. Am. Chem. Soc., 2002, 124, 8067.
59. N. V. Tkachenko, V. Vehmanen, J.-P. Nikkanen, H. Yamada, H. Imahori, S. Fukuzumi and H. Lemmetyinen, Chem. Phys. Lett., 2002, 366, 245.
60. S. Fukuzumi, H. Imahori, K. Okamoto, H. Yamada, M. Fujitsuka, O. Ito and D. M. Guldi, J. Phys. Chem. A, 2002, 106, 1903.
61. N. Ohta, S. Mikami, Y. Iwaki, M. Tsushima, H. Imahori, K. Tamaki, Y. Sakata and S. Fukuzumi, Chem. Phys. Lett., 2003, 368, 230.
62. T. Kesti, N. V. Tkachenko, H. Yamada, H. Imahori, S. Fukuzumi and H. Lemmetyinen, Photochem. Photobiol. Sci., 2003, 2, 251.
63. Kashiwagi, K. Ohkubo, J. A. McDonald, I. M. Blake, M. J. Crossley, Y. Araki, O. Ito, H. Imahori and S. Fukuzumi, Org. Lett., 2003, 5, 2719.
64. N. V. Tkachenko, H. Lemmetyinen, J. Sonoda, K. Ohkubo, T. Sato, H. Imahori and S. Fukuzumi, J. Phys. Chem. A, 2003, 107, 8834.
65. I. Zilbermann, G. A. Anderson, D. M. Guldi, H. Yamada, H. Imahori and S. Fukuzumi, J. Porphyrins Phthalocyanines, 2003, 7, 357.
66. K. Ohkubo, H. Kotani, J. Shao, Z. Ou, Karl M. Kadish, G. Li, R. K. Pandey, M. Fujitsuka, O. Ito, H. Imahori and S. Fukuzumi, Angew. Chem., Int. Ed., 2004, 43, 853.
67. (a) T. Asahi, M. Ohkohchi, R. Matsusaka, N. Mataga, R. P. Zhang, A. Osuka and K. Maruyama, J. Am. Chem. Soc., 1993, 115, 5665;
68. (b) J. M. DeGraziano, P. A. Liddell, L. Leggett, A. L. Moore, T. A. Moore and D. Gust, J. Phys. Chem., 1994, 98, 1758;
69. (c) A. Osuka, G. Noya, S. Taniguchi, T. Okada, Y. Nishimura, I. Yamazaki and N. Mataga, Chem. Eur. J., 2000, 6, 33;
70. (d) A. Nakano, A. Osuka, T. Yamazaki, Y. Nishimura, S. Akimoto, I. Yamazaki, A. Itaya, M. Murakami and H. Miyasaka, Chem. Eur. J., 2001, 7, 3134.
71. D. Gust, T. A. Moore, A. L. Moore, A. N. Macpherson, A. Lopez, J. M. DeGraziano, I. Gouni, E. Bittersmann, G. R. Seely, F. Gao, R. A. Nieman, X. C. Ma, L. J. Demanche, S.-C. Hung, D. K. Luttrull, S.-J. Lee and P. K. Kerrigan, J. Am. Chem. Soc., 1993, 115, 11141.
72. M. R. Wasielewski, G. L. Gains, III, G. P. Wiederrecht, W. A. Svec and M. P. Niemczyk, J. Am. Chem. Soc., 1993, 115, 10442.
73. Y.-Z. Hu, S. Tsukiji, S. Shinkai, S. Oishi and I. Hamachi, J. Am. Chem. Soc., 2000, 122, 241.
74. H. Imahori, D. M. Guldi, K. Tamaki, Y. Yoshida, C. Luo, Y. Sakata and S. Fukuzumi, J. Am. Chem. Soc., 2001, 123, 6617.
75. D. M. Guldi, H. Imahori, K. Tamaki, Y. Kashiwagi, H. Yamada, Y. Sakata and S. Fukuzumi, J. Phys. Chem. B, 2004, 108, 541.
76. H. Imahori, Y. Sekiguchi, Y. Kashiwagi, T. Sato, Y. Araki, O. Ito, H. Yamada and S. Fukuzumi, Chem. Eur. J., 2004, 10, in press.
77. Recently a donor (mesityl)-acceptor (acridinium ion) directly linked dyad has been reported to exhibit the longest lifetime of the charge-separated state (2 h at 203 K) with a high quantum yield (98%) in donor-acceptor linked systems. No π conjugation between the donor and acceptor moieties due to the perpendicular orientation may be responsible for formation of the long-lived charge-separated state with the high quantum yield; see: S. Fukuzumi, H. Kotani, K. Ohkubo, S. Ogo, N. V. Tkachenko and H. Lemmetyinen, J. Am. Chem. Soc., 2004, 126, 1600.
78. N. V. Tkachenko, L. Rantala, A. Y. Tauber, J. Helaja, P. H. Hynninen and H. Lemmetyinen, J. Am. Chem. Soc., 1999, 121, 9378.
79. K. Tamaki, H. Imahori, Y. Nishimura, I. Yamazaki, A. Shimomura, T. Okada and Y. Sakata, Chem. Lett., 1999, 227.
80. H. Imahori, K. Yamada, M. Hasegawa, S. Taniguchi, T. Okada and Y. Sakata, Angew. Chem., Int. Ed., 1997, 36, 2626.
81. S. Higashida, H. Imahori, T. Kaneda and Y. Sakata, Chem. Lett., 1998, 605.
82. K. Tamaki, H. Imahori, Y. Nishimura, I. Yamazaki and Y. Sakata, Chem. Commun., 1999, 625.
83. M. Fujitsuka, O. Ito, H. Imahori, K. Yamada, H. Yamada and Y. Sakata, Chem. Lett., 1999, 721.
84. H. Imahori, K. Tamaki, Y. Araki, T. Hasobe, O. Ito, A. Shimomura, S. Kundu, T. Okada, Y. Sakata and S. Fukuzumi, J. Phys. Chem. A, 2002, 106, 2803.
85. A. Helms, D. Heiler and G. McLendon, J. Am. Chem. Soc., 1992, 114, 6227.
86. (a) N. Aratani and A. Osuka, Bull. Chem. Soc. Jpn., 2001, 74, 1361;
87. (b) N. Aratani, A. Osuka, H. S. Cho and D. Kim, J. Photochem. Photobiol. C, 2002, 3, 25;
88. (c) D. Kim and A. Osuka, J. Phys. Chem. A, 2003, 107, 8791.
89. H. Imahori, K. Tamaki, Y. Araki, Y. Sekiguchi, O. Ito, Y. Sakata and S. Fukuzumi, J. Am. Chem. Soc., 2002, 124, 5165.
90. (a) T. Hasobe, H. Imahori, H. Yamada, T. Sato and S. Fukuzumi, Nano Lett., 2003, 3, 409;
91. (b) T. Hasobe, H. Imahori, H. Yamada and S. Fukuzumi, J. Porphyrins Phthalocyanines, 2003, 7, 296.
92. (a) T. Akiyama, H. Imahori and Y. Sakata, Chem. Lett., 1994, 1447;
93. (b) H. Imahori, H. Norieda, S. Ozawa, K. Ushida, H. Yamada, T. Azuma, K. Tamaki and Y. Sakata, Langmuir, 1998, 14, 5335;
94. (c) H. Imahori, H. Norieda, Y. Nishimura, I. Yamazaki, K. Higuchi, N. Kato, T. Motohiro, H. Yamada, T. Tamaki, M. Arimura and Y. Sakata, J. Phys. Chem. B, 2000, 104, 1253.
95. (a) H. Imahori, T. Azuma, S. Ozawa, H. Yamada, K. Ushida, A. Ajavakom, H. Norieda and Y. Sakata, Chem. Commun., 1999, 557;
96. (b) H. Imahori, T. Azuma, A. Ajavakom, H. Norieda, H. Yamada and Y. Sakata, J. Phys. Chem. B, 1999, 103, 7233.
97. (a) T. Akiyama, H. Imahori, A. Ajavakom and Y. Sakata, Chem. Lett., 1996, 907;
98. (b) H. Yamada, H. Imahori and S. Fukuzumi, J. Mater. Chem., 2002, 12, 2034.
99. (a) D. Hirayama, T. Yamashiro, K. Takimiya, Y. Aso, T. Otsubo, H. Norieda, H. Imahori and Y. Sakata, Chem. Lett., 2000, 570;
100. (b) D. Hirayama, K. Takimiya, Y. Aso, T. Otsubo, T. Hasobe, H. Yamada, H. Imahori, S. Fukuzumi and Y. Sakata, J. Am. Chem. Soc., 2002, 124, 532.
101. (a) H. Imahori, H. Yamada, S. Ozawa, K. Ushida and Y. Sakata, Chem. Commun., 1999, 1165;
102. (b) H. Imahori, H. Yamada, Y. Nishimura, I. Yamazaki and Y. Sakata, J. Phys. Chem. B, 2000, 104, 2099.
103. S. Fukuzumi and H. Imahori, Electron Transfer in Chemistry, ed. V. Balzani, Wiley-VCH, Weinheim, Germany, 2001, Vol. 2, Chapter 8, pp. 927-997.
104. (a) H. Imahori, Y. Nishimura, H. Norieda, H. Karita, I. Yamazaki, Y. Sakata and S. Fukuzumi, Chem. Commun., 2000, 661;
105. (b) H. Imahori, T. Hasobe, H. Yamada, Y. Nishimura, I. Yamazaki and S. Fukuzumi, Langmuir, 2001, 17, 4925;
106. (c) H. Imahori, H. Norieda, H. Yamada, Y. Nishimura, I. Yamazaki, Y. Sakata and S. Fukuzumi, J. Am. Chem. Soc., 2001, 123, 100.
107. (a) H. Yamada, H. Imahori, Y. Nishimura, I. Yamazaki and S. Fukuzumi, Chem. Commun., 2000, 1921;
108. (b) H. Yamada, H. Imahori, Y. Nishimura, I. Yamazaki and S. Fukuzumi, Adv. Mater., 2002, 14, 892;
109. (c) H. Yamada, H. Imahori, Y. Nishimura, I. Yamazaki, T. K. Ahn, S. K. Kim, D. Kim and S. Fukuzumi, J. Am. Chem. Soc., 2003, 125, 9129;
110. (d) H. Imahori, K. Hosomizu, Y. Mori, T. Sato, T. K. Ahn, S. K. Kim, D. Kim, Y. Nishimura, I. Yamazaki, H. Ishii, H. Hotta and Y. Matano, J. Phys. Chem. B, 2004, 108, 5018.
111. (a) H. Imahori, M. Arimura, T. Hanada, Y. Nishimura, I. Yamazaki, Y. Sakata and S. Fukuzumi, J. Am. Chem. Soc., 2001, 123, 335;
112. (b) S. Fukuzumi, Y. Endo, Y. Kashiwagi, Y. Araki, O. Ito and H. Imahori, J. Phys. Chem B, 2003, 107, 11979;
113. (c) H. Imahori, Y. Kashiwagi, T. Hanada, Y. Endo, Y. Nishimura, I. Yamazaki and S. Fukuzumi, J. Mater. Chem., 2003, 13, 2890;
114. (d) H. Imahori, Y. Kashiwagi, Y. Endo, T. Hanada, Y. Nishimura, I. Yamazaki, Y. Araki, O. Ito and S. Fukuzumi, Langmuir, 2004, 20, 73
115. (a) T. Hasobe, S. Fukuzumi, H. Imahori and P. V. Kamat, J. Mater. Chem., 2003, 13, 2515;
116. (b) T. Hasobe, H. Imahori, S. Fukuzumi and P. V. Kamat, J. Phys. Chem. B, 2003, 107, 12105;
117. (c) T. Hasobe, H. Imahori, S. Fukuzumi and P. V. Kamat, J. Am. Chem. Soc., 2003, 125, 14962;
118. (d) T. Hasobe, Y. Kashiwagi, M. Absalom, K. Hosomizu, M. J. Crossley, H. Imahori, P. V. Kamat and S. Fukuzumi, Adv. Mater., 2004, 16, in press.