Vectorial electron relay at ITO electrodes modified with self-assembled monolayers of ferrocene-porphyrin-fullerene triads and porphyrin-fullerene dyads for molecular photovoltaic devices

Chemistry - A European Journal

Volumn 10, Issue 20, 2004, Pages 5111-5122

  Imahori, Hiroshi ^a,b   Kimura, Makoto ^c   Hosomizu, Kohei ^a,b   Sato, Tomoo ^d   Tae, Kyu Ahn ^e,f   Seong, Keun Kim ^f   Kim, Dongho ^e   Nishimura, Yoshimobu ^d   Yamazaki, Iwao ^g   Araki, Yasuyuki ^h   Ito, Osamu ^h   Fukuzumi, Shunichi ^c  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c OSAKA UNIVERSITY   (Japan)

^d UNIVERSITY OF TSUKUBA   (Japan)

^e Yonsei University   (South Korea)

^f Seoul National University   (South Korea)

^g HOKKAIDO UNIVERSITY   (Japan)

^h TOHOKU UNIVERSITY   (Japan)

Author keywords

Donor acceptor systems; Electron transfer; Fullerenes; Porphyrins; Self assembly

Indexed keywords

ELECTRIC CHARGE; ELECTRODES; INDIUM COMPOUNDS; IRON COMPOUNDS; ORGANOMETALLICS; PHOTOCURRENTS; PHOTOVOLTAIC CELLS; SELF ASSEMBLY;

CHARGE-SEPARATION EFFICIENCY; INDIUM TIN OXIDE (ITO) ELECTRODES; MOLECULAR PHOTOVOLTAIC DEVICES; PHOTOSYNTHETIC SYSTEMS; VECTORIAL ELECTRON RELAYS;

FULLERENES;

FERROCENE; FULLERENE; INDIUM TIN OXIDE; PORPHYRIN; PORPHYRIN DERIVATIVE; TIN DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; ATOMIC FORCE MICROSCOPY; CORRELATION ANALYSIS; COVALENT BOND; CYCLIC POTENTIOMETRY; DEVICE; ELECTROCHEMISTRY; ELECTRODE; ELECTRON; MOLECULAR BIOLOGY; PHOTOCHEMISTRY; PHYSICS; QUANTUM CHEMISTRY; ULTRAVIOLET SPECTROSCOPY;

EID: 7044264977     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400377     Document Type: Article

References (137)

1. a) M. R. Wasielewski, Chem. Rev. 1992, 92, 435;
2. b) R. A. Marcus, Angew. Chem. 1993, 105, 1161; Angew. Chem. Int. Ed. Engl. 1993, 32, 1111;
3. b) R. A. Marcus, Angew. Chem. 1993, 105, 1161; Angew. Chem. Int. Ed. Engl. 1993, 32, 1111;
4. c) M. Bixon, J. Jortner, Adv. Chem. Phys. 1999, 106, 35;
5. d) D. Gust, T. A. Moore in The Porphyrin Handbook, Vol. 8 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, pp. 153-190;
6. e) V. Balzani, Electron Transfer in Chemistry, Wiley-VCH, Weinheim, 2001.
7. a) H. Imahori, Y. Sakata, Adv. Mater. 1997, 9, 537;
8. b) H. Imahori, Y. Sakata, Eur. J. Org. Chem. 1999, 2445;
9. c) H. Imahori, Y. Mori, Y. Matano, J. Photochem. Photobiol. C 2003, 4, 51:
10. d) D. M. Guldi, Chem. Commun. 2000, 321;
11. e) H. Imahori, S. Fukuzumi, Adv. Funct. Mater. 2004, 14, 525;
12. f) H. Imahori, J. Phys. Chem. B 2004, 108, 6130;
13. g) H. Imahori, Org. Biomol. Chem. 2004, 2, 1425.
14. a) H. Imahori, K. Hagiwara, T. Akiyama, M. Aoki, S. Taniguchi, T. Okada, M. Shirakawa, Y. Sakata, Chem. Phys. Lett. 1996, 263, 545;
15. b) H. Imahori, N. V. Tkachenko, V. Vehmanen, K. Tamaki, H. Lemmetyinen, Y. Sakata, S. Fukuzumi, J. Phys. Chem. A 2001, 105, 1750;
16. c) H. Imahori, H. Yamada, D. M. Guldi, Y. Endo, A. Shimomura, S. Kundu, K. Yamada, T. Okada, Y. Sakata, S. Fukuzumi, Angew. Chem. 2002, 114, 2450; Angew. Chem. Int. Ed. 2002, 41, 2344.
17. c) H. Imahori, H. Yamada, D. M. Guldi, Y. Endo, A. Shimomura, S. Kundu, K. Yamada, T. Okada, Y. Sakata, S. Fukuzumi, Angew. Chem. 2002, 114, 2450; Angew. Chem. Int. Ed. 2002, 41, 2344.
18. a) A. Ulman, An Introduction to Ultrathin Organic Films, Academic Press, San Diego, 1991;
19. b) J. Jortner, M. A. Ratner, Molecular Electronics, Blackwell, Oxford, 1997;
20. c) C. A. Mirkin, Inorg. Chem. 2000, 39, 2258;
21. d) A. N. Shipway, E. Katz, I. Willner, ChemPhysChem 2000, 1, 18;
22. e) A. P. Alivisatos, P. F. Barbara, A. W. Castleman, J. Chang, D. A. Dixon, M. L. Klein, G. L. McLendon, J. S. Miller, M. A. Ratner, P. J. Rossky, S. I. Stupp, M. E. Thompson, Adv. Mater. 1998, 10, 1297.
23. a) C. A. Mirkin, W. B. Caldwell, Tetrahedron 1996, 52, 5113;
24. b) X. Shi, W. B. Caldwell, K. Chen, C. A. Mirkin, J. Am. Chem. Soc. 1994, 116, 11598;
25. c) W. B. Caldwell, K. Chen, C. A. Mirkin, S. J. Babinec, Langmuir 1993, 9, 1945;
26. d) Y.-S. Shon, K. F. Kelly, N. J. Halas, T. R. Lee, Langmuir 1999, 15, 5329;
27. e) T. Hatano, A. Ikeda, T. Akiyama, S. Yamada, M. Sano, Y. Kanekiyo, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 2000, 5, 909.
28. a) F. Arias, L. A. Godínez, S. R. Wilson, A. E. Kaifer, L. Echegoyen, J. Am. Chem. Soc. 1996, 118, 6086;
29. b) O. Domínguez, L. Echegoyen, F. Cunha, N. Tao, Langmuir 1998, 14, 821;
30. c) L. Echegoyen, L. E. Echegoyen, Acc. Chem. Res. 1998, 31, 593;
31. d) S.-G. Liu, C. Martineau, J.-M. Raimundo, J. Roncali, L. Echegoyen, Chem. Commun. 2001, 913.
32. H. Imahori, T. Azuma, A. Ajavakom, H. Norieda, H. Yamada, Y. Sakata, J. Phys. Chem. B 1999, 103, 7233.
33. a) M. Lahav, T. Gabriel, A. N. Shipway, I. Willner, J. Am. Chem. Soc. 1999, 121, 258;
34. b) M. Lahav, V. Heleg-Shabtai, J. Wasserman, E. Katz, I. Willner, H. Dürr, Y.-Z. Hu, S. H. Bossmann, J. Am. Chem. Soc. 2000, 122, 11480;
35. c) K. Uosaki, T. Kondo, X.-Q. Zhang, M. Yanagida, J. Am. Chem. Soc. 1997, 119, 8367;
36. d) T. Kondo, M. Yanagida, S.-I. Nomura, T. Ito, K. Uosaki, J. Electroanal. Chem. 1997, 438, 121;
37. e) F. B. Abdelrazzaq, R. C. Kwong, M. E. Thompson, J. Am. Chem. Soc. 2002, 124, 4796.
38. a) E. Katz, I. Willner, Langmuir 1997, 13, 3364;
39. b) J. Zak, H. Yuan, M. Ho, L. K. Woo, M. D. Porter, Langmuir 1993, 9, 2772;
40. c) J. E. Hutchison, T. A. Postlethwaite, C.-H. Chen, K. W. Hathcock, R. S. Ingram, W. Ou, R. W. Linton, R. W. Murray, D. A. Tyvoll, L. L. Chng, J. P. Collman, Langmuir 1997, 13, 2143;
41. d) J. E. Hutchison, T. A. Postlethwaite, R. W. Murray, Langmuir 1993, 9, 3277;
42. e) T. R. E. Simpson, D. J. Revell, M. J. Cook, D. A. Russell, Langmuir 1997, 13, 460;
43. f) D. T. Gryko, F. Zhao, A. A. Yasseri, K. M. Roth, D. F. Bocian, W. G. Kuhr, J. S. Lindsey, J. Org. Chem. 2000, 65, 7356.
44. a) G. Ashkenasy, G. Kalyuzhny, J. Libman, I. Rubinstein, A. Shanzer, Angew. Chem. 1999, 111, 1333; Angew. Chem. Int. Ed. 1999, 38, 1257;
45. a) G. Ashkenasy, G. Kalyuzhny, J. Libman, I. Rubinstein, A. Shanzer, Angew. Chem. 1999, 111, 1333; Angew. Chem. Int. Ed. 1999, 38, 1257;
46. b) N. Kanayama, T. Kanbara, H. Kitano, J. Phys. Chem. B 2000, 104, 271;
47. c) D. A. Offord, S. B. Sachs, M. S. Ennis, T. A. Eberspacher, J. H. Griffin, C. E. D. Chidsey, J. P. Collman, J. Am. Chem. Soc. 1998, 120, 4478;
48. d) I. Willner, V. Heleg-Shabtai, E. Katz, H. K. Rau, W. Haehnel, J. Am. Chem. Soc. 1999, 121, 6455;
49. e) E. Soto, J. C. MacDonald, G. F. C. Cooper, W. G. McGimpsey, J. Am. Chem. Soc. 2003, 125, 2838.
50. a) S. Fukuzumi, H. Imahori in Electron Transfer in Chemistry, Vol. 2 (Ed.: V. Balzani), Wiley-VCH, Weinheim, 2001, pp. 927-975;
51. b) H. Imahori, H. Norieda, S. Ozawa, K. Ushida, H. Yamada, T. Azuma, K. Tamaki, Y. Sakata, Langmuir 1998, 14, 5335;
52. c) H. Imahori, H. Norieda, Y. Nishimura, I. Yamazaki, K. Higuchi, N. Kato, T. Motohiro, H. Yamada, K. Tamaki, M. Arimura, Y. Sakata, J. Phys. Chem. B 2000, 104, 1253.
53. a) J. J. Hickman, D. Ofer, C. Zou, M. S. Wrighton, P. E. Laibinis, G. M. Whitesides, J. Am. Chem. Soc. 1991, 113, 1128;
54. b) C. D. Frisbie, J. R. Martin, R. R. Duff, Jr., M. S. Wrighton, J. Am. Chem. Soc. 1992, 114, 7142;
55. c) S. Creager, C. J. Yu, C. Bamdad, S. O'Connor, T. MacLean, E. Lam, Y. Chong, G. T. Olsen, J. Luo, M. Gozin, J. F. Kayyem, J. Am. Chem. Soc. 1999, 121, 1059;
56. d) T. Kondo, S. Horiuchi, I. Yagi, S. Ye, K. Uosaki, J. Am. Chem. Soc. 1999, 121, 391;
57. e) H. Byrd, E. P. Suponeva, A. B. Bocarsly, M. E. Thompson, Nature 1996, 380, 610.
58. a) W. B. Caldwell, D. J. Campbell, K. Chen, B. R. Herr, C. A. Mirkin, A. Malik, M. K. Durbin, P. Dutta, K. G. Huang, J. Am. Chem. Soc. 1995, 117, 6071;
59. b) D. J. Campbell, B. R. Herr, J. C. Hulteen, R. P. Van Duyne, C. A. Mirkin, J. Am. Chem. Soc. 1996, 118, 10211;
60. c) D. G. Walter, D. J. Campbell, C. A. Mirkin, J. Phys. Chem. B 1999, 103, 402.
61. a) I. Willner, Acc. Chem. Res. 1997, 30, 347;
62. b) R. Blonder, S. Levi, G. Tao, I. Ben-Dov, I. Willner, J. Am. Chem. Soc. 1997, 119, 10467;
63. c) A. Doron, M. Portnoy, M. Lion-Dagan, E. Katz, I. Willner, J. Am. Chem. Soc. 1996, 118, 8937;
64. d) T. Morita, S. Kimura, S. Kobayashi, Y. Imanishi, J. Am. Chem. Soc. 2000, 122, 2850;
65. e) K. M. Roth, J. S. Lindsey, D. F. Bocian, W. G. Kuhr, Langmuir 2002, 18, 4030.
66. a) M. A. Fox, Acc. Chem. Res. 1999, 32, 201;
67. b) M. O. Wolf, M. A. Fox, J. Am. Chem. Soc. 1995, 117, 1845;
68. c) M. O. Wolf, M. A. Fox, Langmuir 1996, 12, 955;
69. d) M. A. Fox, M. D. Wooten, Langmuir 1997, 13, 7099;
70. e) W. Li, V. Lynch, H. Thompson, M. A. Fox, J. Am. Chem. Soc. 1997, 119, 7211;
71. f) S. Reese, M. A. Fox, J. Phys. Chem. B 1998, 102, 9820.
72. a) T. Akiyama, H. Imahori, A. Ajavakom, Y. Sakata, Chem. Lett. 1996, 907;
73. b) H. Imahori, S. Ozawa, K. Ushida, M. Takahashi, T. Azuma, A. Ajavakom, T. Akiyama, M. Hasegawa, S. Taniguchi, T. Okada, Y. Sakata, Bull. Chem. Soc. Jpn. 1999, 72, 485;
74. c) H. Imahori, H. Yamada, S. Ozawa, K. Ushida, Y. Sakata, Chem. Commun. 1999, 1165;
75. d) H. Imahori, H. Yamada, Y. Nishimura, I. Yamazaki, Y. Sakata, J. Phys. Chem. B 2000, 104, 2099;
76. e) H. Imahori, H. Norieda, H. Yamada, Y. Nishimura, I. Yamazaki, Y. Sakata, S. Fukuzumi J. Am. Chem. Soc. 2001, 123, 100.
77. a) H. Imahori, Y. Nishimura, H. Norieda, H. Karita, I. Yamazaki, Y. Sakata, S. Fukuumi, Chem. Commun. 2000, 661;
78. b) H. Imahori, T. Hasobe, H. Yamada, Y. Nishimura, I. Yamazaki, S. Fukuzumi, Langmuir 2001, 17, 4925;
79. c) T. Morita, S. Kimura, S. Kobayashi, Y. Imanishi, Chem. Lett. 2000, 676;
80. d) H. Imahori, S. Fukuzumi, Adv. Mater. 2001, 13, 1197.
81. R. W. Murray, Molecular Design of Electrode Surfaces, Wiley, New York, 1992, pp. 1-48.
82. Organic solar cells containing films of donor-linked fullerenes on ITO: a) J.-F. Eckert, J.-F. Nicoud, J.-F. Nierengarten, S.-G. Liu, L. Echegoyen, F. Barigelletti, N. Armaroli, L. Ouali, V. Krasnikov, G. Hadziioannou, J. Am. Chem. Soc. 2000, 122, 7467; b) T. Gu, D. Tsamouras, C. Melzer, V. Krasnikov, J.-P. Gisselbrecht, M. Gross, G. Hadziioannou, J.-F. Nierengarten, ChemPhysChem 2002, 3, 124; c) J.-F. Nierengarten, J.-F. Eckert, J.-F. Nicoud, L. Ouali, V. Krasnikov, G. Hadziioannou, Chem. Commun. 1999, 617; d) E. Peeters, P. A. van Hal, J. Knol, C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, R. A. J. Janssen, J. Phys. Chem. B 2000, 104, 10174.
83. Organic solar cells containing films of donor-linked fullerenes on ITO: a) J.-F. Eckert, J.-F. Nicoud, J.-F. Nierengarten, S.-G. Liu, L. Echegoyen, F. Barigelletti, N. Armaroli, L. Ouali, V. Krasnikov, G. Hadziioannou, J. Am. Chem. Soc. 2000, 122, 7467; b) T. Gu, D. Tsamouras, C. Melzer, V. Krasnikov, J.-P. Gisselbrecht, M. Gross, G. Hadziioannou, J.-F. Nierengarten, ChemPhysChem 2002, 3, 124; c) J.-F. Nierengarten, J.-F. Eckert, J.-F. Nicoud, L. Ouali, V. Krasnikov, G. Hadziioannou, Chem. Commun. 1999, 617; d) E. Peeters, P. A. van Hal, J. Knol, C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, R. A. J. Janssen, J. Phys. Chem. B 2000, 104, 10174.
84. Organic solar cells containing films of donor-linked fullerenes on ITO: a) J.-F. Eckert, J.-F. Nicoud, J.-F. Nierengarten, S.-G. Liu, L. Echegoyen, F. Barigelletti, N. Armaroli, L. Ouali, V. Krasnikov, G. Hadziioannou, J. Am. Chem. Soc. 2000, 122, 7467; b) T. Gu, D. Tsamouras, C. Melzer, V. Krasnikov, J.-P. Gisselbrecht, M. Gross, G. Hadziioannou, J.-F. Nierengarten, ChemPhysChem 2002, 3, 124; c) J.-F. Nierengarten, J.-F. Eckert, J.-F. Nicoud, L. Ouali, V. Krasnikov, G. Hadziioannou, Chem. Commun. 1999, 617; d) E. Peeters, P. A. van Hal, J. Knol, C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, R. A. J. Janssen, J. Phys. Chem. B 2000, 104, 10174.
85. Organic solar cells containing films of donor-linked fullerenes on ITO: a) J.-F. Eckert, J.-F. Nicoud, J.-F. Nierengarten, S.-G. Liu, L. Echegoyen, F. Barigelletti, N. Armaroli, L. Ouali, V. Krasnikov, G. Hadziioannou, J. Am. Chem. Soc. 2000, 122, 7467; b) T. Gu, D. Tsamouras, C. Melzer, V. Krasnikov, J.-P. Gisselbrecht, M. Gross, G. Hadziioannou, J.-F. Nierengarten, ChemPhysChem 2002, 3, 124; c) J.-F. Nierengarten, J.-F. Eckert, J.-F. Nicoud, L. Ouali, V. Krasnikov, G. Hadziioannou, Chem. Commun. 1999, 617; d) E. Peeters, P. A. van Hal, J. Knol, C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, R. A. J. Janssen, J. Phys. Chem. B 2000, 104, 10174.
86. Photoactive SAMs on ITO were reported to generate photocurrent: a) A. Ikeda, T. Hatano, S. Shinkai, T. Akiyama, S. Yamada, J. Am. Chem. Soc. 2001, 123, 4855; b) T.-X. Wei, J. Zhai, J.-H. Ge, L.-B. Gan, C.-H. Huang, G.-B. Luo, L.-M. Ying, T.-T. Liu, X.-S. Zhao, Appl. Surf. Sci. 1999, 151, 153; c) H. Yamada, H. Imahori, Y. Nishimura, I. Yamazaki, S. Fukuzumi, Chem. Commun. 2000, 1921; d) T. Hasobe, H. Imahori, H. Yamada, T. Sato, K. Ohkubo, S. Fukuzumi, Nona Lett. 2003, 3, 409; e) H. Imahori, K. Hosomizu, Y. Mori, T. Sato, T. K. Ahn, S. K. Kim, D. Kim, Y. Nishimura, I. Yamazaki, H. Ishii, H. Hotta, Y. Matano, J. Phys. Chem. B 2004, 108, 5018.
87. Photoactive SAMs on ITO were reported to generate photocurrent: a) A. Ikeda, T. Hatano, S. Shinkai, T. Akiyama, S. Yamada, J. Am. Chem. Soc. 2001, 123, 4855; b) T.-X. Wei, J. Zhai, J.-H. Ge, L.-B. Gan, C.-H. Huang, G.-B. Luo, L.-M. Ying, T.-T. Liu, X.-S. Zhao, Appl. Surf. Sci. 1999, 151, 153; c) H. Yamada, H. Imahori, Y. Nishimura, I. Yamazaki, S. Fukuzumi, Chem. Commun. 2000, 1921; d) T. Hasobe, H. Imahori, H. Yamada, T. Sato, K. Ohkubo, S. Fukuzumi, Nona Lett. 2003, 3, 409; e) H. Imahori, K. Hosomizu, Y. Mori, T. Sato, T. K. Ahn, S. K. Kim, D. Kim, Y. Nishimura, I. Yamazaki, H. Ishii, H. Hotta, Y. Matano, J. Phys. Chem. B 2004, 108, 5018.
88. Photoactive SAMs on ITO were reported to generate photocurrent: a) A. Ikeda, T. Hatano, S. Shinkai, T. Akiyama, S. Yamada, J. Am. Chem. Soc. 2001, 123, 4855; b) T.-X. Wei, J. Zhai, J.-H. Ge, L.-B. Gan, C.-H. Huang, G.-B. Luo, L.-M. Ying, T.-T. Liu, X.-S. Zhao, Appl. Surf. Sci. 1999, 151, 153; c) H. Yamada, H. Imahori, Y. Nishimura, I. Yamazaki, S. Fukuzumi, Chem. Commun. 2000, 1921; d) T. Hasobe, H. Imahori, H. Yamada, T. Sato, K. Ohkubo, S. Fukuzumi, Nona Lett. 2003, 3, 409; e) H. Imahori, K. Hosomizu, Y. Mori, T. Sato, T. K. Ahn, S. K. Kim, D. Kim, Y. Nishimura, I. Yamazaki, H. Ishii, H. Hotta, Y. Matano, J. Phys. Chem. B 2004, 108, 5018.
89. Photoactive SAMs on ITO were reported to generate photocurrent: a) A. Ikeda, T. Hatano, S. Shinkai, T. Akiyama, S. Yamada, J. Am. Chem. Soc. 2001, 123, 4855; b) T.-X. Wei, J. Zhai, J.-H. Ge, L.-B. Gan, C.-H. Huang, G.-B. Luo, L.-M. Ying, T.-T. Liu, X.-S. Zhao, Appl. Surf. Sci. 1999, 151, 153; c) H. Yamada, H. Imahori, Y. Nishimura, I. Yamazaki, S. Fukuzumi, Chem. Commun. 2000, 1921; d) T. Hasobe, H. Imahori, H. Yamada, T. Sato, K. Ohkubo, S. Fukuzumi, Nona Lett. 2003, 3, 409; e) H. Imahori, K. Hosomizu, Y. Mori, T. Sato, T. K. Ahn, S. K. Kim, D. Kim, Y. Nishimura, I. Yamazaki, H. Ishii, H. Hotta, Y. Matano, J. Phys. Chem. B 2004, 108, 5018.
90. Photoactive SAMs on ITO were reported to generate photocurrent: a) A. Ikeda, T. Hatano, S. Shinkai, T. Akiyama, S. Yamada, J. Am. Chem. Soc. 2001, 123, 4855; b) T.-X. Wei, J. Zhai, J.-H. Ge, L.-B. Gan, C.-H. Huang, G.-B. Luo, L.-M. Ying, T.-T. Liu, X.-S. Zhao, Appl. Surf. Sci. 1999, 151, 153; c) H. Yamada, H. Imahori, Y. Nishimura, I. Yamazaki, S. Fukuzumi, Chem. Commun. 2000, 1921; d) T. Hasobe, H. Imahori, H. Yamada, T. Sato, K. Ohkubo, S. Fukuzumi, Nona Lett. 2003, 3, 409; e) H. Imahori, K. Hosomizu, Y. Mori, T. Sato, T. K. Ahn, S. K. Kim, D. Kim, Y. Nishimura, I. Yamazaki, H. Ishii, H. Hotta, Y. Matano, J. Phys. Chem. B 2004, 108, 5018.
91. 2) exhibited photocurrent generation: a) T. Osa, M. Fujihira, Nature 1976, 264, 349; b) M. Fujihira, N. Ohishi, T. Osa, Nature 1977, 268, 226; c) S. Anderson, E. C. Constable, M. P. Dare-Edwards, J. B. Goodenough, A. Hamnett, K. R. Seddon, R. D. Wright, Nature 1979, 280, 571; d) M. A. Fox, F. J. Nobes, T. A. Voynick, J. Am. Chem. Soc. 1980, 102, 4036; e) A. Hagfeldt, M. Grätzel, Acc. Chem. Res. 2000, 33, 269.
92. 2) exhibited photocurrent generation: a) T. Osa, M. Fujihira, Nature 1976, 264, 349; b) M. Fujihira, N. Ohishi, T. Osa, Nature 1977, 268, 226; c) S. Anderson, E. C. Constable, M. P. Dare-Edwards, J. B. Goodenough, A. Hamnett, K. R. Seddon, R. D. Wright, Nature 1979, 280, 571; d) M. A. Fox, F. J. Nobes, T. A. Voynick, J. Am. Chem. Soc. 1980, 102, 4036; e) A. Hagfeldt, M. Grätzel, Acc. Chem. Res. 2000, 33, 269.
93. 2) exhibited photocurrent generation: a) T. Osa, M. Fujihira, Nature 1976, 264, 349; b) M. Fujihira, N. Ohishi, T. Osa, Nature 1977, 268, 226; c) S. Anderson, E. C. Constable, M. P. Dare-Edwards, J. B. Goodenough, A. Hamnett, K. R. Seddon, R. D. Wright, Nature 1979, 280, 571; d) M. A. Fox, F. J. Nobes, T. A. Voynick, J. Am. Chem. Soc. 1980, 102, 4036; e) A. Hagfeldt, M. Grätzel, Acc. Chem. Res. 2000, 33, 269.
94. 2) exhibited photocurrent generation: a) T. Osa, M. Fujihira, Nature 1976, 264, 349; b) M. Fujihira, N. Ohishi, T. Osa, Nature 1977, 268, 226; c) S. Anderson, E. C. Constable, M. P. Dare-Edwards, J. B. Goodenough, A. Hamnett, K. R. Seddon, R. D. Wright, Nature 1979, 280, 571; d) M. A. Fox, F. J. Nobes, T. A. Voynick, J. Am. Chem. Soc. 1980, 102, 4036; e) A. Hagfeldt, M. Grätzel, Acc. Chem. Res. 2000, 33, 269.
95. 2) exhibited photocurrent generation: a) T. Osa, M. Fujihira, Nature 1976, 264, 349; b) M. Fujihira, N. Ohishi, T. Osa, Nature 1977, 268, 226; c) S. Anderson, E. C. Constable, M. P. Dare-Edwards, J. B. Goodenough, A. Hamnett, K. R. Seddon, R. D. Wright, Nature 1979, 280, 571; d) M. A. Fox, F. J. Nobes, T. A. Voynick, J. Am. Chem. Soc. 1980, 102, 4036; e) A. Hagfeldt, M. Grätzel, Acc. Chem. Res. 2000, 33, 269.
96. 2) were reported to generate photocurrent: a) R. Argazzi, C. A. Bignozzi, T. A. Heimer, F. N. Castellano, G. J. Meyer, J. Am. Chem. Soc. 1995, 117, 11815; b) P. Bonhôte, J.-E. Moser, R. Humphry-Baker, N. Vlachopoulos, S. M. Zakeeruddin, L. Walder, M. Grätzel, J. Am. Chem. Soc. 1999, 121, 1324; c) C. J. Kleverlaan, M. T. Indelli, C. A. Bignozzi, L. Pavanin, F. Scandola, G. M. Hasselman, G. J. Meyer, J. Am. Chem. Soc. 2000, 122, 2840; d) P. V. Kamat, S. Barazzouk, S. Hotchandani, K. G. Thomas, Chem. Eur. J. 2000, 6, 3914; e) C. A. Bignozzi, R. Argazzi, C. J. Kleverlaan, Chem. Soc. Rev. 2090, 29, 87; f) Molecular Level Artificial Photosynthetic Materials (Ed.: G. J. Meyer), Wiley, New York, 1997; g) N, Hirata, J.-J. Lagref, E. J. Palomares, J. R. Durrant, M. K. Nazeeruddin, M. Grätzel, D. D. Censo, Chem. Eur. J. 2004, 10, 595.
97. 2) were reported to generate photocurrent: a) R. Argazzi, C. A. Bignozzi, T. A. Heimer, F. N. Castellano, G. J. Meyer, J. Am. Chem. Soc. 1995, 117, 11815; b) P. Bonhôte, J.-E. Moser, R. Humphry-Baker, N. Vlachopoulos, S. M. Zakeeruddin, L. Walder, M. Grätzel, J. Am. Chem. Soc. 1999, 121, 1324; c) C. J. Kleverlaan, M. T. Indelli, C. A. Bignozzi, L. Pavanin, F. Scandola, G. M. Hasselman, G. J. Meyer, J. Am. Chem. Soc. 2000, 122, 2840; d) P. V. Kamat, S. Barazzouk, S. Hotchandani, K. G. Thomas, Chem. Eur. J. 2000, 6, 3914; e) C. A. Bignozzi, R. Argazzi, C. J. Kleverlaan, Chem. Soc. Rev. 2090, 29, 87; f) Molecular Level Artificial Photosynthetic Materials (Ed.: G. J. Meyer), Wiley, New York, 1997; g) N, Hirata, J.-J. Lagref, E. J. Palomares, J. R. Durrant, M. K. Nazeeruddin, M. Grätzel, D. D. Censo, Chem. Eur. J. 2004, 10, 595.
98. 2) were reported to generate photocurrent: a) R. Argazzi, C. A. Bignozzi, T. A. Heimer, F. N. Castellano, G. J. Meyer, J. Am. Chem. Soc. 1995, 117, 11815; b) P. Bonhôte, J.-E. Moser, R. Humphry-Baker, N. Vlachopoulos, S. M. Zakeeruddin, L. Walder, M. Grätzel, J. Am. Chem. Soc. 1999, 121, 1324; c) C. J. Kleverlaan, M. T. Indelli, C. A. Bignozzi, L. Pavanin, F. Scandola, G. M. Hasselman, G. J. Meyer, J. Am. Chem. Soc. 2000, 122, 2840; d) P. V. Kamat, S. Barazzouk, S. Hotchandani, K. G. Thomas, Chem. Eur. J. 2000, 6, 3914; e) C. A. Bignozzi, R. Argazzi, C. J. Kleverlaan, Chem. Soc. Rev. 2090, 29, 87; f) Molecular Level Artificial Photosynthetic Materials (Ed.: G. J. Meyer), Wiley, New York, 1997; g) N, Hirata, J.-J. Lagref, E. J. Palomares, J. R. Durrant, M. K. Nazeeruddin, M. Grätzel, D. D. Censo, Chem. Eur. J. 2004, 10, 595.
99. 2) were reported to generate photocurrent: a) R. Argazzi, C. A. Bignozzi, T. A. Heimer, F. N. Castellano, G. J. Meyer, J. Am. Chem. Soc. 1995, 117, 11815; b) P. Bonhôte, J.-E. Moser, R. Humphry-Baker, N. Vlachopoulos, S. M. Zakeeruddin, L. Walder, M. Grätzel, J. Am. Chem. Soc. 1999, 121, 1324; c) C. J. Kleverlaan, M. T. Indelli, C. A. Bignozzi, L. Pavanin, F. Scandola, G. M. Hasselman, G. J. Meyer, J. Am. Chem. Soc. 2000, 122, 2840; d) P. V. Kamat, S. Barazzouk, S. Hotchandani, K. G. Thomas, Chem. Eur. J. 2000, 6, 3914; e) C. A. Bignozzi, R. Argazzi, C. J. Kleverlaan, Chem. Soc. Rev. 2090, 29, 87; f) Molecular Level Artificial Photosynthetic Materials (Ed.: G. J. Meyer), Wiley, New York, 1997; g) N, Hirata, J.-J. Lagref, E. J. Palomares, J. R. Durrant, M. K. Nazeeruddin, M. Grätzel, D. D. Censo, Chem. Eur. J. 2004, 10, 595.
100. 2) were reported to generate photocurrent: a) R. Argazzi, C. A. Bignozzi, T. A. Heimer, F. N. Castellano, G. J. Meyer, J. Am. Chem. Soc. 1995, 117, 11815; b) P. Bonhôte, J.-E. Moser, R. Humphry-Baker, N. Vlachopoulos, S. M. Zakeeruddin, L. Walder, M. Grätzel, J. Am. Chem. Soc. 1999, 121, 1324; c) C. J. Kleverlaan, M. T. Indelli, C. A. Bignozzi, L. Pavanin, F. Scandola, G. M. Hasselman, G. J. Meyer, J. Am. Chem. Soc. 2000, 122, 2840; d) P. V. Kamat, S. Barazzouk, S. Hotchandani, K. G. Thomas, Chem. Eur. J. 2000, 6, 3914; e) C. A. Bignozzi, R. Argazzi, C. J. Kleverlaan, Chem. Soc. Rev. 2000, 29, 87; f) Molecular Level Artificial Photosynthetic Materials (Ed.: G. J. Meyer), Wiley, New York, 1997; g) N, Hirata, J.-J. Lagref, E. J. Palomares, J. R. Durrant, M. K. Nazeeruddin, M. Grätzel, D. D. Censo, Chem. Eur. J. 2004, 10, 595.
101. 2) were reported to generate photocurrent: a) R. Argazzi, C. A. Bignozzi, T. A. Heimer, F. N. Castellano, G. J. Meyer, J. Am. Chem. Soc. 1995, 117, 11815; b) P. Bonhôte, J.-E. Moser, R. Humphry-Baker, N. Vlachopoulos, S. M. Zakeeruddin, L. Walder, M. Grätzel, J. Am. Chem. Soc. 1999, 121, 1324; c) C. J. Kleverlaan, M. T. Indelli, C. A. Bignozzi, L. Pavanin, F. Scandola, G. M. Hasselman, G. J. Meyer, J. Am. Chem. Soc. 2000, 122, 2840; d) P. V. Kamat, S. Barazzouk, S. Hotchandani, K. G. Thomas, Chem. Eur. J. 2000, 6, 3914; e) C. A. Bignozzi, R. Argazzi, C. J. Kleverlaan, Chem. Soc. Rev. 2090, 29, 87; f) Molecular Level Artificial Photosynthetic Materials (Ed.: G. J. Meyer), Wiley, New York, 1997; g) N, Hirata, J.-J. Lagref, E. J. Palomares, J. R. Durrant, M. K. Nazeeruddin, M. Grätzel, D. D. Censo, Chem. Eur. J. 2004, 10, 595.
102. 2) were reported to generate photocurrent: a) R. Argazzi, C. A. Bignozzi, T. A. Heimer, F. N. Castellano, G. J. Meyer, J. Am. Chem. Soc. 1995, 117, 11815; b) P. Bonhôte, J.-E. Moser, R. Humphry-Baker, N. Vlachopoulos, S. M. Zakeeruddin, L. Walder, M. Grätzel, J. Am. Chem. Soc. 1999, 121, 1324; c) C. J. Kleverlaan, M. T. Indelli, C. A. Bignozzi, L. Pavanin, F. Scandola, G. M. Hasselman, G. J. Meyer, J. Am. Chem. Soc. 2000, 122, 2840; d) P. V. Kamat, S. Barazzouk, S. Hotchandani, K. G. Thomas, Chem. Eur. J. 2000, 6, 3914; e) C. A. Bignozzi, R. Argazzi, C. J. Kleverlaan, Chem. Soc. Rev. 2090, 29, 87; f) Molecular Level Artificial Photosynthetic Materials (Ed.: G. J. Meyer), Wiley, New York, 1997; g) N, Hirata, J.-J. Lagref, E. J. Palomares, J. R. Durrant, M. K. Nazeeruddin, M. Grätzel, D. D. Censo, Chem. Eur. J. 2004, 10, 595.
103. Vectorial photoinduced ET of donor-acceptor dyads in Langmuir-Blodgett (LB) films on ITO was observed: a) N. V. Tkachenko, E. Vuorimaa, T. Kesti, A. S. Alekseev, A. Y. Tauber, P. H. Hynninen, H. Lemmetyinen, J. Phys. Chem. B 2000, 104, 6371; b) A. S. Alekseev, N. V. Tkachenko, A. Y. Tauber, P. H. Hynninen, R. Osterbacka, H. Stubb, H. Lemmetyinen, J. Phys. Chem. B 2002, 275, 243; c) N. V. Tkachenko, A. Y. Tauber, P. H. Hynninen, A. Y. Sharonov, H. Lemmetyinen, J. Phys. Chem. A 1999, 103, 3657.
104. Vectorial photoinduced ET of donor-acceptor dyads in Langmuir-Blodgett (LB) films on ITO was observed: a) N. V. Tkachenko, E. Vuorimaa, T. Kesti, A. S. Alekseev, A. Y. Tauber, P. H. Hynninen, H. Lemmetyinen, J. Phys. Chem. B 2000, 104, 6371; b) A. S. Alekseev, N. V. Tkachenko, A. Y. Tauber, P. H. Hynninen, R. Osterbacka, H. Stubb, H. Lemmetyinen, J. Phys. Chem. B 2002, 275, 243; c) N. V. Tkachenko, A. Y. Tauber, P. H. Hynninen, A. Y. Sharonov, H. Lemmetyinen, J. Phys. Chem. A 1999, 103, 3657.
105. Vectorial photoinduced ET of donor-acceptor dyads in Langmuir-Blodgett (LB) films on ITO was observed: a) N. V. Tkachenko, E. Vuorimaa, T. Kesti, A. S. Alekseev, A. Y. Tauber, P. H. Hynninen, H. Lemmetyinen, J. Phys. Chem. B 2000, 104, 6371; b) A. S. Alekseev, N. V. Tkachenko, A. Y. Tauber, P. H. Hynninen, R. Osterbacka, H. Stubb, H. Lemmetyinen, J. Phys. Chem. B 2002, 275, 243; c) N. V. Tkachenko, A. Y. Tauber, P. H. Hynninen, A. Y. Sharonov, H. Lemmetyinen, J. Phys. Chem. A 1999, 103, 3657.
106. 60 dyad on ITO was reported for the fabrication of photoactive films exhibiting photocurrent generation: C. Luo, D. M. Guldi, M. Maggini, E. Menna, S. Mondini, N. A. Kotov, M. Prato, Angew. Chem. 2000, 112, 4052; Angew. Chem. Int. Ed. 2000, 39, 3905.
107. 60 dyad on ITO was reported for the fabrication of photoactive films exhibiting photocurrent generation: C. Luo, D. M. Guldi, M. Maggini, E. Menna, S. Mondini, N. A. Kotov, M. Prato, Angew. Chem. 2000, 112, 4052; Angew. Chem. Int. Ed. 2000, 39, 3905.
108. For application of electrophoretically deposited metal nanoclusters covered with photoactive chromophores on optically transparent electrodes in the photoelectrochemical conversion of light energy, see: a) P. K. Sudeep, B. I. Ipe, K. G. Thomas, M. V. George, S. Barazzouk, S. Hotchandani, P. V. Kamat, Nano Lett. 2002, 2, 29; b) P. V. Kamat, S. Barazzouk, K. G. Thomas, S. Hotchandani, J. Phys. Chem. B 2000, 104, 4014; c) P. V. Kamat, J. Phys. Chem. B 2002, 106, 7729; d) T. Hasobe, H. Imahori, P. V. Kamat, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 14962.
109. For application of electrophoretically deposited metal nanoclusters covered with photoactive chromophores on optically transparent electrodes in the photoelectrochemical conversion of light energy, see: a) P. K. Sudeep, B. I. Ipe, K. G. Thomas, M. V. George, S. Barazzouk, S. Hotchandani, P. V. Kamat, Nano Lett. 2002, 2, 29; b) P. V. Kamat, S. Barazzouk, K. G. Thomas, S. Hotchandani, J. Phys. Chem. B 2000, 104, 4014; c) P. V. Kamat, J. Phys. Chem. B 2002, 106, 7729; d) T. Hasobe, H. Imahori, P. V. Kamat, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 14962.
110. For application of electrophoretically deposited metal nanoclusters covered with photoactive chromophores on optically transparent electrodes in the photoelectrochemical conversion of light energy, see: a) P. K. Sudeep, B. I. Ipe, K. G. Thomas, M. V. George, S. Barazzouk, S. Hotchandani, P. V. Kamat, Nano Lett. 2002, 2, 29; b) P. V. Kamat, S. Barazzouk, K. G. Thomas, S. Hotchandani, J. Phys. Chem. B 2000, 104, 4014; c) P. V. Kamat, J. Phys. Chem. B 2002, 106, 7729; d) T. Hasobe, H. Imahori, P. V. Kamat, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 14962.
111. For application of electrophoretically deposited metal nanoclusters covered with photoactive chromophores on optically transparent electrodes in the photoelectrochemical conversion of light energy, see: a) P. K. Sudeep, B. I. Ipe, K. G. Thomas, M. V. George, S. Barazzouk, S. Hotchandani, P. V. Kamat, Nano Lett. 2002, 2, 29; b) P. V. Kamat, S. Barazzouk, K. G. Thomas, S. Hotchandani, J. Phys. Chem. B 2000, 104, 4014; c) P. V. Kamat, J. Phys. Chem. B 2002, 106, 7729; d) T. Hasobe, H. Imahori, P. V. Kamat, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 14962.
112. K. Chen, W. B. Caldwell, C. A. Mirkin, J. Am. Chem. Soc. 1993, 115, 1193.
113. a) H. Yamada, H. Imahori, Y. Nishimura, I. Yamazaki, S. Fukuzumi, Adv. Mater. 2002, 14, 892;
114. b) H. Yamada, H. Imahori, Y. Nishimura, I. Yamazaki, T. K. Ahn, S. K. Kim, D. Kim, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 9129.
115. a) H. Imahori, M. E. El-Khouly, M. Fujitsuka, O. Ito, Y. Sakata, S. Fukuzumi, J. Phys. Chem. A 2001, 105, 325;
116. b) C. Luo, D. M. Guldi, H. Imahori, K. Tamaki, Y. Sakata, J. Am. Chem. Soc. 2000, 122, 6535;
117. c) H. Imahori, K. Tamaki, D. M. Guldi, C. Luo, M. Fujitsuka, O. Ito, Y. Sakata, S. Fukuzumi, J. Am. Chem. Soc. 2001, 123, 2607.
118. a) T. J. Kesti, N. V. Tkachenko, V. Vehmanen, H. Yamada, H. Imahori, S. Fukuzumi, H. Lemmetyinen, J. Am. Chem. Soc. 2002, 124, 8067;
119. b) N. V. Tkachenko, H. Lemmetyinen, J. Sonoda, K. Ohkubo, T. Sato, H. Imahori, S. Fukuzumi, J. Phys. Chem. A 2003, 107, 8834.
120. D. Hammel, C. Kautz, K. Müllen, Chem. Ber. 1990, 123, 1353.
121. a) M. Maggini, G. Scorrano, M. Prato, J. Am. Chem. Soc. 1993, 115, 9798;
122. b) M. Prato, M. Maggini, Acc. Chem. Res. 1998, 31, 519.
123. K. Kordatos, S. Bosi, T. Da Ros, A. Zambon, V. Lucchini, M. Prato, J. Org. Chem. 1996, 61, 4764.
124. The regioselectivity of bis-adducts could not be determined because of the complex molecular structures on the ITO surface.
125. [11c] see: R. F. Khairutdinov, N. Serpone, J. Phys. Chem. B 1999, 103, 761.
126. 60 moiety was irreversible. It is known that fullerenes exhibit no reversible electrochemical response when they are embedded in films: N. Nakashima, T. Ishii, M. Shirakusa, T. Nakanishi, H. Murakami, T. Sagara, Chem. Eur. J. 2001, 7, 1766.
127. [11c,16d]
128. [17b] or porphyrin-modified gold nanoclusters in benzonitrile; see: S. Fukuzumi, Y. Endo, Y. Kashiwagi, Y. Araki, O. Ito, H. Imahori, J. Phys. Chem. B 2003, 107, 11979.
129. 60/ITO under the present experimental conditions.
130. 2P-ref) result from self-quenching of the porphyrin excited singlet state due to aggregation on ITO.
131. The fluorescence lifetime of similar porphyrin-fullerene dyads incorporated in LB systems is known to be short relative to that in solution. Accelerated photoinduced ET is suggested in the LB film: N. V. Tkachenko, V. Vehmanen, J.-P. Nikkanen, H. Yamada, H. Imahori, S. Fukuzumi, H. Lemmetyinen, Chem. Phys. Lett. 2002, 366, 245.
132. 60 radical anion (around 1000 nm) could not be confirmed because of poor signal-to-noise ratio. The input laser power was minimized to avoid exciton-exciton annihilation processes, which occur dominantly within a few picoseconds after laser excitation, especially at high power.
133. N. V. Tkachenko, L. Rantala, A. Y. Tauber, J. Helaja, P. H. Hynninen, H. Lemmetyinen, J. Am. Chem. Soc. 1999, 121, 9378.
134. [16b]
135. a) N. Boens, N. Tamai, I. Yamazaki, T. Yamazaki, Photochem. Photobiol. 1990, 52, 911;
136. b) Y. Nishimura, A. Yasuda, S. Speiser, I. Yamazaki, Chem. Phys. Lett. 2000, 323, 117.
137. H. S. Cho, N. W. Song, Y. H. Kim, S. C. Jeoung, S. Hahn, D. Kim, S. K. Kim, N. Yoshida, A. Osuka, J. Phys. Chem. A 2000, 104, 3287.