Intermolecular and supramolecular photoinduced electron transfer processes of fullerene-porphyrin/phthalocyanine systems

Journal of Photochemistry and Photobiology C: Photochemistry Reviews

Volumn 5, Issue 1, 2004, Pages 79-104

  El Khouly, Mohamed E ^a,c,d,e   Ito, Osamu ^a   Smith, Phillip M ^b   D'Souza, Francis ^b,f,g,h,i  

^a TOHOKU UNIVERSITY   (Japan)

^b WICHITA STATE UNIVERSITY   (United States)

^c Kafr Elsheikh Branch   (Egypt)

^d TANTA UNIVERSITY   (Egypt)

^e CHIBA UNIVERSITY   (Japan)

^f UNIVERSITY OF MYSORE   (India)

^g INDIAN INSTITUTE OF SCIENCE   (India)

^h UNIVERSITY OF HOUSTON   (United States)

ⁱ UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

Charge recombination; Charge separation; Fullerenes; Intermolecular interactions; Photoinduced electron transfer; Phthalocyanines; Porphyrins; Self assembly; Supramolecules

Indexed keywords

CHARGE SEPARATION; INTERMOLECULAR ELECTRON TRANSFER; POLAR SOLVENTS;

CHARGE TRANSFER; COMPLEXATION; MOLECULAR STRUCTURE; REACTION KINETICS; SOLVENTS; SUPRAMOLECULAR CHEMISTRY;

PHOTOCHEMICAL REACTIONS;

EID: 2442453629     PISSN: 13895567     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochemrev.2004.01.003     Document Type: Review

References (123)

1. H.D. Roth, A brief history of photoinduced electron transfer and related reactions, in: J. Mattay (Ed.), Topics in Current Chemistry, vol. 156, Springer-Verlage, Berlin, 1990, pp. 1.
2. J.S. Connolly, J.R. Bolton, in: M.A. Fox, M. Chanon (Eds.), Photoinduced Electron Transfer, Elsevier, Amsterdam, 1988.
3. Kavarnos G.J., Turro N.G. Chem. Rev. 86:1986;401
4. M.R. Wasielewski, D.G. Johnson, W.A. Svec, K.M. Kersey, D.E. Cragg, D.W. Minsek, in: J.R. Norris, D. Meisel (Eds.), Photochemical Energy Conversion, Elsevier, Amsterdam, 1989.
5. Mattes S., Farid S. Science. 226:1984;917
6. D.F. Eaton, Electron transfer process in imaging, in: J. Mattay (Ed.), Topics in Current Chemistry, Springe-Verlage, Berlin, 1990, p. 199.
7. Wasielewski M.R. Chem. Rev. 92:1992;435
8. G.J. Kavarnos (Ed.), Fundamentals of Photoinduced Electron Transfer, VCH Publisher, New York, 1993, p. 103.
9. D. Gust, T.A. Moore, A.L. Moore, in: Z.W. Tian, Y. Cao (Eds.), Photochemical and Photoelectrochemical Conversion and Storage of Solar Energy, International Academic Publishers, Beijing, 1993.
10. C. Stegeman, P. Likamwa, in: A. Miller, K.R. Welford, B. Daino (Eds.), Nonlinear Optical Materials and Devices for Applications in Information Technology, Kluwer Academic Publishers, Amsteradm, 1995.
11. J. Deisenhofer, in: J.R. Norris (Ed.), The Photosynthetic Reaction Center, Academic Press, San Diego, 1993.
12. R.E. Blankenship, M.T. Madigan, C.E. Bauer (Eds.), Anoxygenic Photosynthetic Bacteria, Kluwer Academic Publishers, Dordrecht, 1995.
13. D. Gust, T.A. Moore, A.L. Moore, in: F.S. Sterrett (Ed.), Alternative Fuels and the Environment, Lewis Publishers, Chelsea, 1995.
14. J.S. Connolly (Ed.), Photochemical Conversion and Storage of Solar Energy, Academic Press, New York, 1981.
15. V. Balzani (Ed.), Electron Transfer in Chemistry, vol. I-V, Wiley-VCH, Weinheim, 2001.
16. Rehm D., Weller A. Isr. J. Chem. 8:1970;259
17. Weller A.Z. Phys. Chem. 132:1982;93
18. D. Gust, T.A. Moore, in: K.M. Kadish, K. Smith, R. Guilard (Eds.), The Porphyrin Handbook, vol. 8, Academic Press, San Diego, 2000, pp. 153-190.
19. Gust D., Moore T.A., Moore A.L. Acc. Chem. Res. 26:1993;198
20. Yoshihara K., Kumazaki S. J. Photochem. Photobiol. C: Rev. 1:2000;22
21. I. Okura (Ed.), Photosensitization of Porphryins and Phthalocyanines, Gordon and Breach Science Publishers, Amsteradm, 2001.
22. Amao Y., Okura I. J. Mol. Catal. B: Enzym. 17:2002;9
23. Amao Y., Asai K., Miyashita T., Okura I. Polym. Adv. Technol. 11:2000;705
24. Maruyama K., Osuka A., Mataga N. Pure Appl. Chem. 66:1994;867
25. Osuka A., Mataga N., Okada T. Pure Appl. Chem. 69:1997;797
26. H.Z. Staab, R. Hauck, B. Popp, Eur. J. Org. Chem. (1998) 631.
27. Häberle T., Hirsch J., Pöllinger F., Heitele H., Michel-Beyerle M.E., Ander C., Döhling A., Krieger C., Rückemann A., Staab H.A. J. Phys. Chem. 100:1996;18269
28. Kilsa K., Kajanus J., Macpherson A.N., Martensson J., Albinsson B. J. Am. Chem. Soc. 123:2001;3069
29. Korth O., Wiehe A., Kurreck H., Roder B. Chem. Phys. 246:1999;363
30. Williamson D.A., Bowler B.E. Inorg. Chim. Acta. 297:2000;47
31. Sing Y.-P., Huang W., Guduru R., Martin R.B. Chem. Phys. Lett. 353:2002;353
32. C.S. Foote, in: K. Prassides (Ed.), Physics and Chemistry of the Fullerenes, Kluwer Academic Publishers, Amsteradm, 1994, p. 79.
33. D.M. Guldi, P.V. Kamat, in: K.M. Kadish, R.S. Ruoff, (Eds.), Fullerenes, Chemistry, Physics and Technology, Wiley-Interscience, New York, 2000, p. 225.
34. Nath S., Pal H., Sapre A.V. Chem. Phys. Lett. 360:2002;422
35. Diederich F., Thilgen C. Science. 271:1996;317
36. Imahori H., Sakata Y. Adv. Mater. 9:1997;537
37. A. Hirsch (Ed.), The Chemistry of the Fullerenes, Georg Thieme, Stuttgart, 1994.
38. Xie Q., Perez-Cordero E., Echegoyen L. J. Am. Chem. Soc. 114:1992;3978
39. Nierengarten J.-F., Eckert J.-F., Felder D., Nicoud J.-F., Armaroli N., Marconi G., Vicinelli V., Boudon C., Gisselbrecht J.-P., Gross M., Hadziioannou G., Krasilkov V., Ouali L., Echegoyen L., Liu S.-G. Carbon. 38:2000;1587
40. Allemand P.M., Koch A., Wudl F., Rubin Y., Diederich F., Alvarez M.M., Anz S.J., Whetten R.L. J. Am. Chem. Soc. 113:1991;1050
41. Dubois D., Kadish K.M., Flanagan S., Haufler R.E., Chibante L.P.F., Wilson L.J. J. Am. Chem. Soc. 114:1992;4364
42. A. Watanabe, O. Ito, H. Saito, M. Watanabe, M. Koishi, J. Chem. Soc., Chem. Commun. (1996) 117.
43. Guldi D.M., Luo C., Prato M., Troisi A., Zerbetto F., Scheloske M., Dietel E., Bauer W., Hirsch A. J. Am. Chem. Soc. 123:2001;9166
44. Luo C., Fujitsuka M., Watanabe A., Ito O., Gan L., Huang Y., Huang C.-H. J. Chem. Soc., Faraday Trans. 94(4):1998;527
45. Alam M.M., Watanabe A., Ito O. Bull. Chem. Soc. Jpn. 70(8):1997;1833
46. Watanabe A., Ito O. J. Phys. Chem. 98:1994;7736
47. Ito O., Sasaki Y., Yoshikawa Y., Watanabe A. J. Phys. Chem. 99:1995;9838
48. Imahori H., Mori Y., Matano J. J. Photochem. Photobiol C: Photochem. Rev. 4:2003;51
49. Guldi D.M. Chem. Soc. Rev. 31:2002;22
50. Fukuzumi S., Imahori H., Yamada H., El-Khouly M.E., Fujitsuka M., Ito O., Guldi D.M. J. Am. Chem. Soc. 123:2001;2571
51. Fukuzumi S., Imahori H., Okamoto K., Yamada H., Fujitsuka M., Ito O., Guldi D.M. J. Phys. Chem. A. 106:2002;1903
52. Ohkubo K., Imahori H., Shao J., Ou Z., Kadish K.M., Chen Y., Zheng G., Pandey R.K., Fujitsuka M., Ito O., Fukuzumi S. J. Phys. Chem. A. 106:2002;10991
53. K.M. Smith (Ed.), Porphyrins and Metalloporphyrins, Elsevier, Amsterdam, 1975.
54. S. Takagi, H. Inoue, in: V. Ramamurthy, K.S. Schanze (Eds.), Multimetallic and Macromolecular Inorganic Photochemistrt, Marcel Dekker, New York, 1999, pp. 215-342.
55. Azim S.A., El-Kemary M.A., El-Daly S.A., El-Daly H.A., El-Khouly M.E., Ebeid Z.M. J. Chem. Soc., Faraday Trans. 92:1996;747
56. Owens J.W., Smith R., Robinson R., Robins M. Inorg. Chim. Acta. 279:1998;226
57. Tsuda A., Osuka A. Science. 93:2001;79
58. J.-H. Chou, M.E. Kosal, H.S. Nalwa, N.A. Rakow, K.S. Suslick, in: K.M. Kadish, K.M. Smith, R. Guilard (Eds.), The Porphyrin Handbook, vol. 6, Academic Press, New York, 2000.
59. Lee C., Lee D.H., Hong J-I. Tetrahedron Lett. 42:2001;8665
60. Armstrong N.R. J. Porphyrins Phthalocyanines. 4:2000;414
61. Blank A., Galili T., Levanon H. J. Porphyrins Phthalocyanines. 5:2001;58
62. Hwang K.C., Mauzerall D. J. Am. Chem. Soc. 114:1992;9705
63. Hwang K.C., Mauzerall D. Nature. 361:1993;138
64. Milanesio M.E., Gervaldo M., Otero L.A., Sereno L., Silber J.J., Durantin E.N. J. Phys. Org. Chem. 15:2002;844
65. Guldi D.M., Neta P., Asmus K.-D. J. Phys. Chem. 98:1994;4617
66. Fujisawa Y., Yasunori O., Yamauchi S. Chem. Phys. Lett. 282:1998;181
67. Fujisawa Y., Yasunori O., Yamauchi S. Chem. Phys. Lett. 294:1998;248
68. Martino D.M., van Willigen H. J. Phys. Chem. A. 104:2000;10701
69. Nojiri T., Watanabe A., Ito O. J. Phys. Chem. A. 102:1998;5215
70. El-Khouly M.E., Fujitsuka M., Ito O. J. Porphyrins Phthalocyanines. 4:2000;591
71. Nojiri T., Alam M.M., Konami H., Watanabe A., Ito O. J. Phys. Chem. A. 101:1997;7943
72. T. Da Ros, M. Prato, D.M. Guldi, E. Alessio, M. Ruzzi, L. Pasimeni, Chem. Commun. (1999) 635.
73. Da Ros T., Prato M., Guldi D.M., Ruzzi M., Pasimeni L. Chem. Eur. J. 7:2001;816
74. D.M. Guldi, C. Luo, T. Da Ros, M. Prato, E. Dietel, A. Hirsch, Chem. Commun. (2000) 375.
75. D.M. Guldi, C. Luo, A. Swartz, M. Scheloske, A. Hirsch, Chem. Commun. (2001) 1066.
76. Diederich F., Lopez M.G. Chem. Soc. Rev. 28:1999;263
77. Piotrowiak P. Chem. Soc. Rev. 28:1999;143
78. D'Souza F., Deviprasad G.D., El-Khouly M.E., Fujitsuka M., Ito O. J. Am. Chem. Soc. 123:2001;5277
79. D'Souza F., Deviprasad G.R., Zandler M.E., Hoang V.T., Arkady K., van Stipdonk M., Perera A., El-Khouly M.E., Fujitsuka M., Ito O. J. Phys. Chem. A. 106:2002;3243
80. D'Souza F., Deviprasad G.R., Zandler M.E., El-Khouly M.E., Fujitsuka M., Ito O. J. Phys. Chem. B. 106:2002;4952
81. Yin G., Xu D., Xu Z. Chem. Phys. Lett. 365:2002;232
82. Weinkauf J.R., Cooper S.W., Schweiger A., Wamser C.C. J. Phys. Chem. A. 107:2003;3486
83. Bettelheim A., Ozer D., Harth R. J. Electroanal. Chem. 226:1989;93
84. Gunduz N., Gunduz T., Hayvali M. Talanta. 48:1999;71
85. Wrobel D., Lukasiewicz J., Goc J., Waszkowiak A., Ion R. J. Mol. Struct. 555:2000;407
86. M. Gouterman, in: D. Dolphin (Ed.), Porphyrins, vol. III, Academic Press, New York, 1978.
87. Ramsdell A., Wamser C.C. J. Phys. Chem. 96:1992;10572
88. Lin C.-l., Fang M.-Y., Cheng S.-H. J. Electro. Chem. 531:2002;155
89. S.I. Murov, Handbook of Photochemistry, Marcel Dekker, New York, 1985.
90. K. Kalyanasundaram, Photochemistry of Polypyridine and Porphyrin Complexes, Academic Press, London 1992.
91. Steren C.A., von Willigen H., Biczok L., Gupta N., Linschitz H. J. Phys. Chem. 100:1996;8920
92. Alam M.M., Watanabe A., Ito O. J. Photochem. Photobiol. A: Chem. 104:1997;59
93. El-Khouly M.E., Fujitsuka M., Ito O. Phys. Chem. Chem. Phys. 4:2002;3322
94. Roy J.K., Cattol F.A., Whitten D.G. J. Am. Chem. Soc. 96:1974;6349
95. El-Khouly M.E., Araki Y., Fujitsuka M., Ito O. Photochem. Photobiol. 74:2001;22
96. A.J. Hoff, J. Amesz, in: H. Scheer (Ed.), Chlorophylls, CRC Press, Boca Raton, 1992, p. 723.
97. H. Scheer, in: W.M. Horspool, P.-S. Song (Eds.), Organic Photochemistry and Photobiology, CRC Press, Boca Raton, 1995, p. 1402.
98. Guergous-Kuras M., Boudreaux B., Joliet A., Joliot P., Redding K. Biophysics. 98:2001;4437
99. Hales B., Bolton J.R. J. Am. Chem. Soc. 49:1972;3314
100. Itoh S., Iwaki M., Ikegami I. Bioenergetics. 1507:2001;115
101. El-Khouly M.E., Islam S.D.-M., Fujitsuka M., Ito O. J. Porphyrins Phthalocyanines. 4:2000;713
102. F.H. Moser, A.L. Thomas, The Phthalocyanines, CRC Press, Boca Raton, FL, 1983.
103. C.C. Lenzoff, A.Z.P. Lever (Eds.), Phthalocyanines, Properties and Applications, VCH Publishers Inc., New York, 1989.
104. Law K.-Y. Chem. Rev. 93:1993;449
105. Komel S., Tromberg B.J., Robeters W.G., Bern M.W. Photochem. Photobiol. 50:1989;175
106. Shirota Y. J. Mater. Chem. 10:2000;1
107. Kumar G.A., Thomas J., Unnikrishnan N.V., Nampoori V.P.N., Vallabhan C.P.G. J. Porphyrins Phthalocyanines. 5:2001;456
108. Kobayashi N. Coord. Chem. Rev. 227:2002;129
109. Antonietta Loi M., Denk P., Hoppe H., Neugebauer H., Winder C., Meissner D., Brabes C., Sariciftci N.S., Gouloumis A., Vzquez P., Torres T. J. Mater. Chem. 13:2003;700
110. Morenzin J., Sclebusch C., Kessler B., Eberhardt W. Phys. Chem. Chem. Phys. 1:1999;1765
111. Hwang K.C., Mauzerall D. J. Am. Chem. Soc. 114:1992;9705
112. Luo H., Fujitsuka M., Ito O., Kimura M. J. Photochem. Photobiol. A: Chem. 156:2003;31
113. El-Khouly M.E., Rogers L.M., Zandler M.E., Gadde S., Fujitsuka M., Ito O., D'Souza F. Chem. Phys. Chem. 4:2003;474
114. D'Souza F., Deviprasad G.R., Rahman M.S., Choi J.-P. Inorg. Chem. 38:1999;2157
115. N. Armaroli, F. Diederich, L. Echegoyen, T. Habicher, L. Flamigni, G. Marconi, J.-F. Nierengarten, New J. Chem. (1999) 77.
116. F. D'Souza, N.P. Rath, G.R. Deviprasad, M.E. Zandler, Chem. Commun. (2001) 267.
117. S.R. Wilson, S. MacMahon, F.T. Tat, P.D. Jarowski, D.I. Schuster, Chem. Commun. (2003) 226.
118. D'Souza F., Deviprasad G.R., Zandler M.E., El-Khouly M.E., Fujitsuka M., Ito O. J. Phys. Chem. A. 107:2003;4801
119. D'Souza F., Deviprasad G.D., El-Khouly M.E., Fujitsuka M., Ito O. J. Am. Chem. Soc. 123:2001;5277
120. El-Khouly M.E., Gadde S., Deviprasad G.R., Fujitsuka M., Ito O. J. Porphyrins Phthalocyanines. 7:2003;1
121. N. Solladié, M.E. Walther, M. Gross, T.M.F. Duarte, C. Bourgogne, J.-F. Nierengarten, Chem. Commun. (2003) 2412.
122. D.M. Guldi, J. Ramey, M.V. Martinez-Diaz, A. de la Escosura, T. Torres, T. Da Ros, M. Prato, Chem. Commun. (2002) 2774.
123. Watanabe N., Kihara N., Furusho Y., Takata T., Araki Y., Ito O. Angew. Chem., Int. Ed. 42:2003;681