Photovoltaic properties of self-assembled monolayers of porphyrins and porphyrin-fullerene dyads on ITO and gold surfaces

Journal of the American Chemical Society

Volumn 125, Issue 30, 2003, Pages 9129-9139

  Yamada, Hiroko ^a   Imahori, Hiroshi ^b,c   Nishimura, Yoshinobu ^c,d   Yamazaki, Iwao ^d   Ahn, Tae Kyu ^e,f   Kim, Seong Keun ^f   Kim, Dongho ^e   Fukuzumi, Shunichi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c KYOTO UNIVERSITY   (Japan)

^d HOKKAIDO UNIVERSITY   (Japan)

^e Yonsei University   (South Korea)

^f Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC FORCE MICROSCOPY; ELECTROCHEMICAL ELECTRODES; FLUORESCENCE; GOLD; PHOTOCURRENTS; PHOTOVOLTAIC EFFECTS; QUENCHING; SELF ASSEMBLY; SYNTHESIS (CHEMICAL);

PHOTOSYNTHETIC DEVICES;

FULLERENES;

FULLERENE DERIVATIVE; GOLD; PORPHYRIN DERIVATIVE; TRIETHANOLAMINE;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; ELECTRODE; ENERGY TRANSFER; FLUORESCENCE; MEASUREMENT; MOLECULAR INTERACTION; PHOTOCHEMISTRY; PHOTOSYNTHESIS; SELF ASSEMBLED MONOLAYER; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0042868648     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034913f     Document Type: Article

References (134)

1. (a) Ulman, A. An Introduction to Ultrathin Organic Films; Academic Press: San Diego, 1991.
2. (b) Molecular Electronics; Jortner, J., Ratner, M. Eds.; Blackwell Science: Oxford, 1997.
3. (c) Mirkin, C. A. Inorg. Chem. 2000, 39, 2258.
4. (d) Shipway, A. N.; Katz, E.; Willner, I. ChemPhysChem 2000, 1, 18.
5. (e) Alivisatos, A. P.; Barbara, P. F.; Castleman, A. W.; Chang, J.; Dixon, D. A.; Klein, M. L.; McLendon, G. L.; Miller, I. S.; Ratner, M. A.; Rossky, P. J.; Stupp, S. I.; Thompson, M. E. Adv. Mater. 1998, 10, 1297.
6. (a) Mirkin, C. A.; Caldwell, W. B. Tetrahedron 1996, 52, 5113.
7. (b) Shi, X.; Caldwell, W. B.; Chen, K.; Mirkin, C. A. J. Am. Chem. Soc. 1994, 116, 11598.
8. (c) Caldwell, W. B.; Chen, K.; Mirkin, C. A.; Babinec, S. J. Langmuir 1993, 9, 1945.
9. (d) Shon, Y.-S.; Kelly, K. F.; Halas, N. J.; Lee, T. R. Langmuir 1999, 15, 5329.
10. (e) Hatano, T.; Ikeda, A.; Akiyama, T.; Yamada, S.; Sano, M.; Kanekiyo, Y.; Shinkai, S. J. Chem. Soc., Perkin Trans. 2 2000, 5, 909.
11. (a) Arias, F.; Godínez, L. A.; Wilson, S. R.; Kaifer, A. E.; Echegoyen, L. J. Am. Chem. Soc. 1996, 118, 6086.
12. (b) Domínguez, O.; Echegoyen, L.; Cunha, F.; Tao, N. Langmuir 1998, 14, 821.
13. (c) Echegoyen, L.; Echegoyen, L. E. Acc. Chem. Res. 1998, 31, 593.
14. (d) Liu, S.-G.; Martineau, C.; Raimundo, J.-M.; Roncali, J.; Echegoyen, L. Chem. Commun. 2001, 913.
15. Imahori, H.; Azuma, T.; Ajavakom, A.; Norieda, H.; Yamada, H.; Sakata, Y. J. Phys. Chem. B 1999, 103, 7233.
16. (a) Lahav, M.; Gabriel, T.; Shipway, A. N.; Willner, I. J. Am. Chem. Soc. 1999, 121, 258.
17. (b) Lahav, M.; Heleg-Shabtai, V.; Wasserman, J.; Katz, E.; Willner, I.; Dürr, H.; Hu, Y.-Z.; Bossmann, S. H. J. Am. Chem. Soc. 2000, 122, 11480.
18. (c) Uosaki, K.; Kondo, T.; Zhang, X.-Q.; Yanagida, M. J. Am. Chem. Soc. 1997, 119, 8367.
19. (d) Kondo, T.; Yanagida, M.; Nomura, S.-i.; Ito, T.; Uosaki, K. J. Electroanal. Chem. 1997, 438, 121.
20. (e) Abdelrazzaq, F. B.; Kwong, R. C.; Thompson, M. E. J. Am. Chem. Soc. 2002, 124, 4796.
21. (a) Katz, E.; Willner, I. Langmuir 1997, 13, 3364.
22. (b) Zak, J.; Yuan, H.; Ho, M.; Woo, L. K.; Porter, M. D. Langmuir 1993, 9, 2772.
23. (c) Hutchison, J. E.; Postlethwaite, T. A.; Chen, C.-h.; Hathcock, K. W.; Ingram, R. S.; Ou, W.; Linton, R. W.; Murray, R. W.; Tyvoll, T. A.; Chng, L. L.; Collman, J. P. Langmuir 1997, 13, 2143.
24. (d) Hutchison, J. E.; Postlethwaite, T. A.; Murray, R. W. Langmuir 1993, 9, 3277.
25. (e) Simpson, T. R. E.; Revell, D. J.; Cook, M. J.; Russell, D. A. Langmuir 1997, 13, 460.
26. (f) Gryko, D. T.; Zhao, F.; Yasseri, A. A.; Roth, K. M.; Bocian, D. F.; Kuhr, W. G.; Lindsey, J. S. J. Org. Chem. 2000, 65, 7356.
27. (a) Ashkenasy, G.; Kalyuzhny, G.; Libman, J.; Rubinstein, I.; Shanzer, A. Angew. Chem., Int. Ed. 1999, 38, 1257.
28. (b) Kanayama, N.; Kanbara, T.; Kitano, H. J. Phys. Chem. B 2000, 104, 271.
29. (c) Offord, D. A.; Sachs, S. B.; Ennis, M. S.; Eberspacher, T. A.; Griffin, J. H.; Chidsey, C. E. D.; Collman, J. P. J. Am. Chem. Soc. 1998, 120, 4478.
30. (d) Willner, I.; Heleg-Shabtai, V.; Katz, E.; Rau, H. K.; Haehnel, W. J. Am. Chem. Soc. 1999, 121, 6455.
31. (a) Fukuzumi, S.; Imahori, H. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 927-975.
32. (b) Imahori, H.; Norieda, H.; Ozawa, S.; Ushida, K.; Yamada, H.; Azuma, T.; Tamaki, K.; Sakata, Y. Langmuir 1998, 14, 5335.
33. (c) Imahori, H.; Norieda, H.; Nishimura, Y.; Yamazaki, I.; Higuchi, K.; Kato, N.; Motohiro, T.; Yamada, H.; Tamaki, K.; Arimura, M.; Sakata, Y. J. Phys. Chem. B 2000, 104, 1253.
34. (a) Hickman, J. J.; Ofer, D.; Zou, C.; Wrighton, M. S.; Laibinis, P. E.; Whitesides, G. M. J. Am. Chem. Soc. 1991, 113, 1128.
35. (b) Frisbie, C. D.; Martin, J. R.; Duff, R. R., Jr.; Wrighton, M. S. J. Am. Chem. Soc. 1992, 114, 7142.
36. (c) Creager, S.; Yu, C. J.; Bamdad, C.; O'Connor, S.; MacLean, T.; Lam, E.; Chong, Y.; Olsen, G. T.; Luo, J.; Gozin, M.; Kayyem, J. F. J. Am. Chem. Soc. 1999, 121, 1059.
37. (d) Kondo, T.; Horiuchi, S.; Yagi, I.; Ye, S.; Uosaki, K. J. Am. Chem. Soc. 1999, 121, 391.
38. (e) Byrd, H.; Suponeva, E. P.; Bocarsly, A. B.; Thompson, M. E. Nature 1996, 380, 610.
39. (a) Caldwell, W. B.; Campbell, D. J.; Chen, K.; Herr, B. R.; Mirkin, C. A.; Malik, A.; Durbin, M. K.; Dutta, P.; Huang, K. G. J. Am. Chem. Soc. 1995, 117, 6071.
40. (b) Campbell, D. J.; Herr, B. R.; Hulteen, J. C.; Van Duyne, R. P.; Mirkin, C. A. J. Am. Chem. Soc. 1996, 118, 10211.
41. (c) Walter, D. G.; Campbell, D. J.; Mirkin, C. A. J. Phys. Chem. B 1999, 103, 402.
42. (a) Willner, I. Acc. Chem. Res. 1997, 30, 347.
43. (b) Blonder, R.; Levi, S.; Tao, G.; Ben-Dov, I.; Willner, I. J. Am. Chem. Soc. 1997, 119, 10467.
44. (c) Doron, A.; Portnoy, M.; Lion-Dagan, M.; Katz, E.; Willner, I. J. Am. Chem. Soc. 1996, 118, 8937.
45. (d) Morita, T.; Kimura, S.; Kobayashi, S.; Imanishi, Y. J. Am. Chem. Soc. 2000, 122, 2850.
46. (e) Roth, K. M.; Lindsey, J. S.; Bocian, D. F.; Kuhr, W. G. Langmuir 2002, 18, 4030.
47. (a) Fox, M. A. Acc. Chem. Res. 1999, 32, 201.
48. (b) Wolf, M. O.; Fox, M. A. J. Am. Chem. Soc. 1995, 117, 1845.
49. (c) Wolf, M. O.; Fox, M. A. Langmuir 1996, 12, 955.
50. (d) Fox, M. A.; Wooten, M. D. Langmuir 1997, 13, 7099.
51. (e) Li, W.; Lynch, V.; Thompson, H.; Fox, M. A. J. Am. Chem. Soc. 1997, 119, 7211.
52. (f) Reese, S.; Fox, M. A. J. Phys. Chem. B 1998, 102, 9820.
53. (a) Akiyama, T.; Imahori, H.; Ajavakom, A.; Sakata, Y. Chem. Lett. 1996, 907.
54. (b) 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.
55. (c) Imahori, H.; Yamada, H.; Ozawa, S.; Ushida, K.; Sakata, Y. Chem. Commun. 1999, 1165.
56. (d) Imahori, H.; Yamada, H.; Nishimura, Y.; Yamazaki, I.; Sakata, Y. J. Phys. Chem. B 2000, 104, 2099.
57. (e) Imahori, H.; Norieda, H.; Yamada, H.; Nishimura, Y.; Yamazaki, I.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 100.
58. (f) Hirayama, D.; Yamashiro, T.; Takimiya, K.; Aso, Y.; Otsubo, T.; Norieda, H.; Imahori, H.; Sakata, Y. Chem. Lett. 2000, 570.
59. (a) Imahori, H.; Nishimura, Y.; Norieda, H.; Karita, H.; Yamazaki, I.; Sakata, Y.; Fukuzumi, S. Chem. Commun. 2000, 661.
60. (b) Imahori, H.; Hasobe, T.; Yamada, H.; Nishimura, Y.; Yamazaki, I.; Fukuzumi, S. Langmuir 2001, 17, 4925.
61. (c) Morita, T.; Kimura, S.; Kobayashi, S.; Imanishi, Y. Chem. Lett. 2000, 676.
62. (d) Imahori, H.; Fukuzumi, S. Adv. Mater. 2001, 13, 1197.
63. (a) Suto, S.; Uchida, W.; Yashima, M.; Goto, T. Phys. Rev. B 1987, 35, 4393.
64. (b) Choudhury, B.; Weedon, A. C.; Bolton, J. R. Langmuir 1998, 14, 6199.
65. (c) Molecular Design of Electrode Surfaces; Murray, R. W., Ed.; John Wiley & Sons: New York, 1992; pp 1-48.
66. (a) Eckert, J.-F.; Nicoud, J.-F.; Nierengarten, J.-F.; Liu, S.-G.; Echegoyen, L.; Barigelletti, F.; Armaroli, N.; Ouali, L.; Krasnikov, V.; Hadziioannou, G. J. Am. Chem. Soc. 2000, 122, 7467.
67. (b) Gu, T.; Tsamouras, D.; Melzer, C.; Krasnikov, V.; Gisselbrecht, J. P.; Gross, M.; Hadziioannou, G.; Nierengarten, J. O. ChemPhysChem 2002, 3, 124.
68. (c) Nierengarten, J.-F.; Eckert, J.-F.; Nicoud, J.-F.; Ouali, L.; Krasnikov, V.; Hadziioannou, G. Chem. Commun. 1999, 617.
69. (d) Peeters, E.; van Hal, P. A.; Knol, J.; Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C.; Janssen, R. A. J. J. Phys. Chem. B 2000, 104, 10174.
70. (a) Obeng, Y. S.; Bard, A. J. Langmuir 1991, 7, 195.
71. (b) Chen, K.; Caldwell, W. B.; Mirkin, C. A. J. Am. Chem. Soc. 1993, 115, 1193.
72. (c) Ikeda, A.; Hatano, T.; Shinkai, S.; Akiyama, T.; Yamada, S. J. Am. Chem. Soc. 2001, 123, 4855.
73. (d) Wei, T.-X.; Zhai, J.; Ge, J.-H.; Gan, L.-B.; Huang, C.-H.; Luo, G.-B.; Ying, L.-M.; Liu, T.-T.; Zhao, X.-S. Appl. Surf. Sci. 1999, 151, 153.
74. (e) Hasobe, T.; Imahori, H.; Yamada, H.; Sato, T.; Ohkubo, K.; Fukuzumi, S. Nano Lett. 2003, 3, 409.
75. 2) have revealed photocurrent generation; see: (a) Osa, T.; Fujihira, M. Nature 1976, 264, 349. (b) Fujihira, M.; Ohishi, N.; Osa, T. Nature 1977, 268, 226. (c) Anderson, S.; Constable, E. C.; Dare-Edwards, M. P.; Goodenough, J. B.; Hamnett, A.; Seddon, K. R.; Wright, R. D. Nature 1979, 280, 571. (d) Fox, M. A.; Nobes, F. J.; Voynick, T. A. J. Am. Chem. Soc. 1980, 102, 4036. (e) Hagfeldt, A.; Grätzel, M. Acc. Chem. Rev. 2000, 33, 269.
76. 2) have revealed photocurrent generation; see: (a) Osa, T.; Fujihira, M. Nature 1976, 264, 349. (b) Fujihira, M.; Ohishi, N.; Osa, T. Nature 1977, 268, 226. (c) Anderson, S.; Constable, E. C.; Dare-Edwards, M. P.; Goodenough, J. B.; Hamnett, A.; Seddon, K. R.; Wright, R. D. Nature 1979, 280, 571. (d) Fox, M. A.; Nobes, F. J.; Voynick, T. A. J. Am. Chem. Soc. 1980, 102, 4036. (e) Hagfeldt, A.; Grätzel, M. Acc. Chem. Rev. 2000, 33, 269.
77. 2) have revealed photocurrent generation; see: (a) Osa, T.; Fujihira, M. Nature 1976, 264, 349. (b) Fujihira, M.; Ohishi, N.; Osa, T. Nature 1977, 268, 226. (c) Anderson, S.; Constable, E. C.; Dare-Edwards, M. P.; Goodenough, J. B.; Hamnett, A.; Seddon, K. R.; Wright, R. D. Nature 1979, 280, 571. (d) Fox, M. A.; Nobes, F. J.; Voynick, T. A. J. Am. Chem. Soc. 1980, 102, 4036. (e) Hagfeldt, A.; Grätzel, M. Acc. Chem. Rev. 2000, 33, 269.
78. 2) have revealed photocurrent generation; see: (a) Osa, T.; Fujihira, M. Nature 1976, 264, 349. (b) Fujihira, M.; Ohishi, N.; Osa, T. Nature 1977, 268, 226. (c) Anderson, S.; Constable, E. C.; Dare-Edwards, M. P.; Goodenough, J. B.; Hamnett, A.; Seddon, K. R.; Wright, R. D. Nature 1979, 280, 571. (d) Fox, M. A.; Nobes, F. J.; Voynick, T. A. J. Am. Chem. Soc. 1980, 102, 4036. (e) Hagfeldt, A.; Grätzel, M. Acc. Chem. Rev. 2000, 33, 269.
79. 2) have revealed photocurrent generation; see: (a) Osa, T.; Fujihira, M. Nature 1976, 264, 349. (b) Fujihira, M.; Ohishi, N.; Osa, T. Nature 1977, 268, 226. (c) Anderson, S.; Constable, E. C.; Dare-Edwards, M. P.; Goodenough, J. B.; Hamnett, A.; Seddon, K. R.; Wright, R. D. Nature 1979, 280, 571. (d) Fox, M. A.; Nobes, F. J.; Voynick, T. A. J. Am. Chem. Soc. 1980, 102, 4036. (e) Hagfeldt, A.; Grätzel, M. Acc. Chem. Rev. 2000, 33, 269.
80. 2) have been reported to generate photocurrent; see: (a) Argazzi, R.; Bignozzi, C. A.; Heimer, T. A.; Castellano, F. N.; Meyer, G. J. J. Am. Chem. Soc. 1995, 117, 11815. (b) Bonhôte, P.; Moser, J.-E.; Humphry-Baker, R.; Vlachopoulos, N.; Zakeeruddin, S. M.; Walder, L.; Grätzel, M. J. Am. Chem. Soc. 1999, 121, 1324. (c) Kleverlaan, C. J.; Indelli, M. T.; Bignozzi, C. A.; Pavanin, L.; Scandola, F.; Hasselman, G. M.; Meyer, G. J. J. Am. Chem. Soc. 2000, 122, 2840. (d) Kamat, P. V.; Barazzouk, S.; Hotchandani, S.; Thomas, K. G. Chem.-Eur. J. 2000, 6, 3914.
81. 2) have been reported to generate photocurrent; see: (a) Argazzi, R.; Bignozzi, C. A.; Heimer, T. A.; Castellano, F. N.; Meyer, G. J. J. Am. Chem. Soc. 1995, 117, 11815. (b) Bonhôte, P.; Moser, J.-E.; Humphry-Baker, R.; Vlachopoulos, N.; Zakeeruddin, S. M.; Walder, L.; Grätzel, M. J. Am. Chem. Soc. 1999, 121, 1324. (c) Kleverlaan, C. J.; Indelli, M. T.; Bignozzi, C. A.; Pavanin, L.; Scandola, F.; Hasselman, G. M.; Meyer, G. J. J. Am. Chem. Soc. 2000, 122, 2840. (d) Kamat, P. V.; Barazzouk, S.; Hotchandani, S.; Thomas, K. G. Chem.-Eur. J. 2000, 6, 3914.
82. 2) have been reported to generate photocurrent; see: (a) Argazzi, R.; Bignozzi, C. A.; Heimer, T. A.; Castellano, F. N.; Meyer, G. J. J. Am. Chem. Soc. 1995, 117, 11815. (b) Bonhôte, P.; Moser, J.-E.; Humphry-Baker, R.; Vlachopoulos, N.; Zakeeruddin, S. M.; Walder, L.; Grätzel, M. J. Am. Chem. Soc. 1999, 121, 1324. (c) Kleverlaan, C. J.; Indelli, M. T.; Bignozzi, C. A.; Pavanin, L.; Scandola, F.; Hasselman, G. M.; Meyer, G. J. J. Am. Chem. Soc. 2000, 122, 2840. (d) Kamat, P. V.; Barazzouk, S.; Hotchandani, S.; Thomas, K. G. Chem.-Eur. J. 2000, 6, 3914.
83. 2) have been reported to generate photocurrent; see: (a) Argazzi, R.; Bignozzi, C. A.; Heimer, T. A.; Castellano, F. N.; Meyer, G. J. J. Am. Chem. Soc. 1995, 117, 11815. (b) Bonhôte, P.; Moser, J.-E.; Humphry-Baker, R.; Vlachopoulos, N.; Zakeeruddin, S. M.; Walder, L.; Grätzel, M. J. Am. Chem. Soc. 1999, 121, 1324. (c) Kleverlaan, C. J.; Indelli, M. T.; Bignozzi, C. A.; Pavanin, L.; Scandola, F.; Hasselman, G. M.; Meyer, G. J. J. Am. Chem. Soc. 2000, 122, 2840. (d) Kamat, P. V.; Barazzouk, S.; Hotchandani, S.; Thomas, K. G. Chem.-Eur. J. 2000, 6, 3914.
84. 60 dyad incorporated noncovalently into Langmuir-Blodgett (LB) films on ITO was confirmed by time-resolved Maxwell displacement charge measurements; see: (a) Tkachenko, N. V.; Vuorimaa, E.; Kesti, T.; Alekseev, A. S.; Tauber, A. Y. Hynninen, P. H.; Lemmetyinen, H. J. Phys. Chem. B 2000, 104, 6371. (b) Tkachenko, N. V.; Vehmanen, V.; Nikkanen, J.-P.; Yamada, H.; Imahori, H.; Fukuzumi, S.; Lemmetyinen, H. Chem. Phys. Lett. 2002, 366, 245.
85. 60 dyad incorporated noncovalently into Langmuir-Blodgett (LB) films on ITO was confirmed by time-resolved Maxwell displacement charge measurements; see: (a) Tkachenko, N. V.; Vuorimaa, E.; Kesti, T.; Alekseev, A. S.; Tauber, A. Y. Hynninen, P. H.; Lemmetyinen, H. J. Phys. Chem. B 2000, 104, 6371. (b) Tkachenko, N. V.; Vehmanen, V.; Nikkanen, J.-P.; Yamada, H.; Imahori, H.; Fukuzumi, S.; Lemmetyinen, H. Chem. Phys. Lett. 2002, 366, 245.
86. 60 dyad on ITO was reported for the fabrication of photoactive films exhibiting photocurrent generation; see: Luo, C.; Guldi, D. M.; Maggini, M.; Menna, E.; Mondini, S.; Kotov, N. A.; Prato, M. Angew. Chem., Int. Ed. 2000, 39, 3905.
87. (a) Martin, N.; Sánchez, L.; Illescas, B.; Pérez, I. Chem. Rev. 1998, 98, 2527.
88. (b) Prato, M. J. Mater. Chem. 1997, 7, 1097.
89. (c) Diederich, F.; Gómez-López, M. Chem. Soc. Rev. 1999, 28, 263.
90. (d) Guldi, D. M.; Kamat, P. V. In Fullerenes; Kadish, K. M., Ruoff, R. S., Eds.; John Wiley & Sons: New York, 2000; Chapter 5, pp 225-281.
91. (e) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40.
92. (f) Jensen, A. W.; Wilson, S. R.; Schuster, D. I. Bioorg. Med. Chem. 1996, 4, 767.
93. (g) Verhoeven, J. W. Adv. Chem. Phys. 1999, 106, 603.
94. (a) Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537.
95. (b) Imahori, H.; Sakata, Y. Eur. J. Org. Chem. 1999, 2445, 5.
96. (c) Guldi, D. M. Chem. Commun. 2000, 321.
97. (d) Guldi, D. M.; Prato, M. Acc. Chem. Res. 2000, 33, 695.
98. (e) Imahori, H.; Mori, Y.; Matano, Y. J. Photochem. Photobiol., C 2003, 4, 51.
99. (a) Imahori, H.; Hagiwara, K.; Akiyama, T.; Aoki, M.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. Chem. Phys. Lett. 1996, 263, 545.
100. (b) Tkachenko, N. V.; Guenther, C.; Imahori, H.; Tamaki, K.; Sakata, Y.; Fukuzumi, S.; Lemmetyinen, H. Chem. Phys. Lett. 2000, 326, 344.
101. (c) Imahori, H.; Tamaki, K.; Yamada, H.; Yamada, K.; Sakata, Y.; Nishimura, Y.; Yamazaki, I.; Fujitsuka, M.; Ito, O. Carbon 2000, 38, 1599.
102. (d) Imahori, H.; Tkachenko, N. V.; Vehmanen, V.; Tamaki, K.; Lemmetyinen, H.; Sakata, Y.; Fukuzumi, S. J. Phys. Chem. A 2001, 105, 1750.
103. (e) Vehmanen, V.; Tkachenko, N. V.; Imahori, H.; Fukuzumi, S.; Lemmetyinen, H. Spectrochimica Acta, Part A 2001, 57, 2229.
104. (f) Imahori, H.; Yamada, H.; Guldi, D. M.; Endo, Y.; Shimomura, A.; Kundu, S.; Yamada, K.; Okada, T.; Sakata, Y.; Fukuzumi, S. Angew. Chem., Int. Ed. 2002, 41, 2344.
105. (g) Kesti, T. J.; Tkachenko, N. V.; Vehmanen, V.; Yamada, H.; Imahori, H.; Fukuzumi, S.; Lemmetyinen, H. J. Am. Chem. Soc. 2002, 124, 8067.
106. (h) Imahori, H.; Tamaki, K.; Araki, Y.; Sekiguchi, Y.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2002, 124, 5165.
107. Guldi, D. M.; Asmus, K.-D. J. Am. Chem. Soc. 1997, 119, 5744.
108. Yamada, H.; Imahori, H.; Nishimura, Y.; Yamazaki, I.; Fukuzumi, S. Chem. Commun. 2000, 1921.
109. Yamada, H.; Imahori, H.; Fukuzumi, S. Adv. Mater. 2002, 14, 892.
110. Imahori, H.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Phys. Chem. A 2001, 105, 325.
111. Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771.
112. (a) Tamaki, K.; Imahori, H.; Nishimura, Y.; Yamazaki, I.; Sakata, Y. Chem. Commun. 1999, 625.
113. (b) Luo, C.; Guldi, D. M.; Imahori, H.; Tamaki, K.; Sakata, Y. J. Am. Chem. Soc. 2000, 122, 6535.
114. (c) Imahori, H.; Tamaki, K.; Guldi, D. M.; Luo, C.; Fujitsuka, M.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 2607.
115. 2P/Au were reported to be due to the partially stacked side-by-side porphyrin aggregation in the SAM; see: Khairutdinov, R. F.; Serpone, N. J. Phys. Chem. B 1999, 103, 761.
116. Synthetic porphyrin dimers in close proximity generally exhibit a negative shift of the oxidation potential due to the interaction between the porphyrins. On the other hand, the decreased dielectric constant in the nonpolar monolayer as compared to that of bulk solution results in the positive shift of the oxidation potential of the porphyrin. Such compensation may be responsible for a small difference in the oxidation potential of the porphyrin in the monolayer and in the solution.
117. -2.
118. TEA may form a complex with the porphyrin SAM on ITO electrode, when the rate of photoinduced electron transfer from TEA to the excited state of porphyrin SAM becomes independent of TEA concentration.
119. (a) Chan, S.-F.; Chou, M.; Creutz, C.; Matsubara, T.; Sutin, N. J. Am. Chem. Soc. 1981, 103, 369.
120. (b) Downard, A. J.; Surridge, N. A.; Gould, S.; Meyer, T. J.; Deronzier, A.; Moutet, J.-C. J. Phys. Chem. 1990, 94, 6754.
121. (c) Matsuoka, S.; Yamamoto, K.; Ogata, T.; Kusaba, M.; Nakashima, N.; Fujita, E.; Yanagida, S. J. Am. Chem. Soc. 1993, 115, 601.
122. (d) Aoki, A.; Abe, Y.; Miyashita, T. Langmuir 1999, 15, 1463.
123. -1; see: Weber, K.; Hockett, L.; Creager, S. J. Phys. Chem. B 1997, 101, 8286.
124. McCallien, D. W. J.; Burn, P. L.; Anderson, H. L. J. Chem. Soc., Perkins Trans 1997, 2581.
125. 2 as electron acceptors.
126. Andersson, M.; Davidsson, J.; Hammarström, L.; Korppi-Tommola, J.; Peltola, T. J. Phys. Chem. B 1999, 103, 3258.
127. This may be ascribed to association between the porphyrin and hexyl viologen, in which the hexyl moiety might be buried within the hydrophobic SAM at the assembly solution interface; see: Creager, S. E.; Collard, D. M.; Fox, M. A. Langmuir 1990, 6, 1617.
128. Akins, D. L.; Özçelik, S.; Zhu, H.-R.; Guo, C. J. Phys. Chem. 1996, 100, 14390.
129. 2P-ref (9.9 ns in THF).
130. 2P radical cation (around 660 nm) and C60 radical anion (around 1000 nm) could not be confirmed because of the 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 with high power.
131. 2+ (0.56 eV).
132. (a) Boens, N.; Tamai, N.; Yamazaki, I.; Yamazaki, T. Photochem. Photobiol. 1990, 52, 911.
133. (b) Nishimura, Y.; Yasuda, A.; Speiser, S.; Yamazaki, I. Chem. Phys. Lett. 2000, 323, 117.
134. Cho, H. S.; Song, N. W.; Kim, Y. H.; Jeoung, S. C.; Hahn, S.; Kim, D.; Kim, S. K.; Yoshida, N.; Osuka, A. J. Phys. Chem. A 2000, 104, 3287.