Long-lived charge-separated states of simple electron donor-acceptor dyads using porphyrins and phthalocyanines

Journal of Porphyrins and Phthalocyanines

Volumn 12, Issue 9, 2008, Pages 993-1004

  Ohkubo, Kei ^a   Fukuzumi, Shunichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Charge separation; Donor acceptor dyad; Lewis acid; Marcus theory; Photoinduced electron transfer; Photosynthesis; Reorganization energy

Indexed keywords

EID: 56749178864     PISSN: 10884246     EISSN: None     Source Type: Journal    
DOI: 10.1142/S1088424608000376     Document Type: Conference Paper

References (149)

1. a) The Photosynthetic Reaction Center Deisenhofer J and Norris JR (Eds) Academic Press: San Diego, 1993.
2. b) Anoxygenic Photosynthetic Bacteria Blankenship RE, Madigan MT and Bauer CE (Eds.) Kluwer Academic Publishing: Dordrecht, 1995.
3. a) Gust D, Moore TA and Moore AL. in Electron Transfer in Chemistry Vol. 3; Balzani V (Ed.) Wiley-VCH: Weinheim, 2001; pp. 272-336.
4. b) Gust D, Moore TA and Moore AL. Acc. Chem. Res. 1993; 26: 198-205.
5. a) Paddon-Row MN. Acc. Chem. Res. 1994; 27: 18-25.
6. b) Verhoeven JW. Adv. Chem. Phys. 1999; 106: 603-644.
7. c) Pasman P, Rob F and Verhoeven, JW. J. Am. Chem. Soc. 1982; 104: 5127-5133.
8. d) Mes GF, Van Ramesdonk HJ and Verhoeven JW. J. Am. Chem. Soc. 1984; 106: 1335-1340.
9. e) Pasman P, Mes GF, Koper, NW and Verhoeven JW. J. Am. Chem. Soc. 1985; 107: 5839-5843.
10. f) Warman JM, De Haas MP, Paddon-Low MN, Cotsaris E, Hush NS, Oevering H and Verhoeven JW. Nature 1986; 320: 615-616.
11. g) Oevering H, Paddon-Low MN, Heppener M, Oliver AM, Cotsaris E, Verhoeven JW and Hush NS. J. Am. Chem. Soc. 1987; 109: 3258-3269.
12. h) Bixon M, Jortner J and Verhoeven JW. J. Am. Chem. Soc. 1994; 116: 7349-7355.
13. i) van Walree CA, Roest MR, Schuddeboom W, Jenneskens LW, Verhoeven JW, Warman JM, Kooijman H and Spek, AL. J. Am. Chem. Soc. 1996; 118: 8395-8407.
14. a) Harriman A and Sauvage JP. Chem. Soc. Rev. 1996; 25: 41-48.
15. b) Blanco MJ, Consuelo Jiménez M, Chambron JC, Heitz V, Linke M and Sauvage JP. Chem. Soc. Rev. 1999; 28: 293-305.
16. c) Chambron JC, Collin JP, Dalbavie JO, Dietrich-Buchecker CO, Heitz V, Odobel F, Solladie N and Sauvage JP. Coord. Chem. Rev. 1998; 178-180: 1299-1312.
17. a) Wasielewski MR. Chem. Rev. 1992; 92: 435-461.
18. b) Debreczeny MP, Svec WA and Wasielewski MR. Science 1996; 274: 584-587.
19. Jordan KD and Paddon-Row MN. Chem. Rev. 1992; 92: 395-410.
20. a) Osuka A, Mataga N and Okada T. Pure Appl. Chem. 1997; 69; 797-802.
21. b) Maruyama K, Osuka A and Mataga N. Pure Appl. Chem. 1994; 66, 867-872.
22. Fukuzumi S and Guldi DM. in Electron Transfer in Chemistry Vol. 2; Balzani V. (Ed.) Wiley-VCH: Weinheim, 2001; pp. 270-337.
23. a) Imahori H, Hagiwara K, Aoki M, Akiyama T, Taniguchi S, Okada T, Shirakawa M and Sakata YY. J. Am. Chem. Soc. 1996; 118: 11771-11782.
24. b) Luo C, Guldi DM, Imahori H, Tamaki K and Sakata Y. J. Am. Chem. Soc. 2000; 122: 6535-6551.
25. c) Imahori H, Tamaki K, Guldi DM, Luo C, Fujitsuka M, Ito O, Sakata Y and Fukuzumi S. J. Am. Chem. Soc. 2001; 123: 2607-2617.
26. d) Imahori H, Tamaki K, Araki Y, Sekiguchi Y, Ito O, Sakata Y and Fukuzumi S. J. Am. Chem. Soc. 2002; 124: 5165-5174;
27. e) Kesti TJ, Tkachenko NV, Vehmanen V, Yamada H, Imahori H, Fukuzumi S and Lemmetyinen H. J. Am. Chem. Soc. 2002; 124: 8067-8077.
28. a) Gust D and Moore TA. in The Porphyrin Handbook Vol. 8; Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press; San Diego, CA, 2000; pp. 153-190.
29. b) Gust D, Moore TA and Moore AL. Acc. Chem. Res. 2001; 34: 40-48.
30. a) Liddell PA, Kuciauskas D, Sumida JP, Nash B, Nguyen D, Moore AL, Moore TA and Gust D. J. Am. Chem. Soc. 1997; 119: 1400-1405.
31. b) Carbonera D, Di Valentin M, Corvaja C, Agostini G, Giacometti G, Liddell PA, Kuciauskas D, Moore AL, Moore TA and Gust D. J. Am. Chem. Soc. 1998: 120; 4398-4405.
32. c) Kuciauskas D, Liddell PA, Moore AL, Moore TA and Gust D. J. Am. Chem. Soc. 1998; 120: 10880-10886.
33. d) Kuciauskas D, Liddell PA, Lin S, Johnson TE, Weghorn SJ, Lindsey JS, Moore AL, Moore TA and Gust D. J. Am. Chem. Soc. 1999; 121: 8604-8614.
34. Gust D, Moore TA, Moore AL, Lee SJ, Bittersmann E, Luttrull DK, Rehms AA, DeGraziano JM, Ma XC, Gao F, Belford RE and Trier TT. Science 1990; 248: 199-201.
35. a) Moser CC, Keske JM, Warncke K, Farid RS and Dutton PL. Nature 1992; 355: 796-802;
36. b) Page CC, Moser CC, Chen X and Dutton PL. Nature 1999; 402: 47-52.
37. a) Martín N, Sánchez L, Illescas B and Pérez I. Chem. Rev. 1998; 98: 2527-2548.
38. b) Segura JL and Martín N. Angew. Chem., Int. Ed. 2001; 40: 1372-1409.
39. c) Giacalone F, Segura JL, Martín N and Guldi DM. J. Am. Chem. Soc. 2004; 126: 5340-5341.
40. d) Diederich F and Gómez-López M. Chem. Rev. Soc. 1999; 28: 263-277.
41. a) Williams RM, Zwier JM and Verhoeven JW. J. Am. Chem. Soc. 1995; 117: 4093-4099.
42. b) Williams RM, Koeberg M, Lawson JM, An YZ, Rubin Y, Paddon-Row MN and Verhoeven JW. J. Org. Chem. 1996; 61: 5055-5062.
43. a) Baran PS, Monaco RR, Khan AU, Schuster DI and Wilson SR. J. Am. CAem. Soc. 1997; 119: 8363-8364.
44. b) Schuster DI, Cheng P, Wilson SR, Prokhorenko V, Katterle M, Holzwarth AR, Braslavsky SE, Klihm G, Williams RM and Luo C. J. Am. Chem. Soc. 1999; 121: 11599-11600.
45. c) Nierengarten JF, Schall C and Nicoud JF. Angew. Chem. Int. Ed. 1998; 37: 1934-1936.
46. d) Eckert JF, Nicoud JF, Nierengarten JF, Liu SG, Echegoyen L, Barigelletti F, Armaroli N, Ouali L, Krasnikov V and Hadziioannou G. J. Am. Chem. Soc. 2000; 122; 7467-7479.
47. a) Montforts FP and Kutzki O. Angew. Chem., Int. Ed. 2000; 39: 599-601.
48. b) Guldi DM, Maggini M, Scorrano G and Prato M. J. Am. Chem. Soc. 1997; 119: 974-980.
49. c) Guldi DM and Prato M. Acc. Chem. Res. 2000; 33: 695-703.
50. a) Balzani V, Juris A, Venturi M, Campagna S and Serroni S. Chem. Rev. 1996; 96: 759-834.
51. b) Arkin MR, Stemp EDA, Holmlin RE, Barton JK, Hormann A, Olson EJC and Barbara PF. Science 1996; 273: 475-480.
52. a) Lewis FD, Liu X, Liu J, Miller SE, Hayes RT and Wasielewski MR. Nature 2000; 406: 51-53.
53. b) Lewis FD, Letsinger RL and Wasielewski MR. Acc. Chem. Res. 2001; 34: 159-170 .
54. a) Imahori H, Guldi DM, Tamaki K, Yoshida Y, Luo C, Sakata Y and Fukuzumi S. J. Am. Chem. Soc. 2001; 123: 6617-6628.
55. b) Guldi DM, Imahori H, Tamaki K, Kashiwagi Y, Yamada H, Sakata Y and Fukuzumi S. J. Phys. Chem. A 2004; 108: 541-548.
56. a) Fukuzumi S, Ohkubo K, Imahori H, Shao J, Ou Z, Zheng G, Chen Y, Pandey RK, Fujitsuka M, Ito O and Kadish KM. J. Am. Chem. Soc. 2001; 123: 10676-10683.
57. b) Ohkubo K, Kotani H, Shao J, Ou Z, Kadish KM, Li G, Pandey RK, Fujitsuka M, Ito O, Imahori H and Fukuzumi S. Angew. Chem. Int. Ed. 2004; 43: 853-856.
58. Fukuzumi S, Kotani H, Ohkubo K, Ogo S, Tkachenko NV and Lemmetyinen H. J. Am. Chem. Soc. 2004; 126: 1600-1601.
59. a) Marcus RA and Sutin N. Biochim. Biophys. Acta 1985; 811: 265-322.
60. b) Marcus RA. Angew. Chem. Int. Ed. Engl. 1993; 32: 1111-1121.
61. a) Closs GL and Miller, JR. Science 1988; 240: 440-447.
62. b) Gould IR and Farid S. Acc. Chem. Res. 1996; 29: 522-528.
63. c) McLendon G. Acc. Chem. Res. 1988; 21: 160-167;
64. d) Winkler JR and Gray HB. Chem. Rev. 1992; 92: 369-379;
65. e) McLendon G and Hake R. Chem. Rev. 1992; 92, 481-490.
66. f) Fukuzumi S, Yoshida Y, Urano T, Suenobu T and Imahori H. J. Am. Chem. Soc. 2001; 123: 11331-11332.
67. g) Mataga N and Miyasaka H. Adv. Chem. Phys. 1999; 107: 431-496.
68. Marcus RA. Angew. Chem., Int. Ed. Engl. 1993; 32: 1111-1121.
69. a) Hush NS. In Mechanistic Aspects of Inorganic Reactions, Rorabacher DB and Endicott JF. (Eds.) ACS Symp. Ser.: No. 198, 1982; p. 301.
70. b) Hush NS. Coord. Chem. Rev. 1985; 64: 135-157.
71. Fukuzumi S. In The Porphyrin Handbook Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: San Diego, 2000; Vol. 8, pp 115-151.
72. Fukuzumi S, Endo Y and Imahori H. J. Am. Chem. Soc. 2002; 124: 10974-10975.
73. Guldi DM and Fukuzumi S. In Fullerenes: From Synthesis to Optoelectronic Properties Guldi, DM and Martin N. (Eds.) Kluwer: Dordrecht, 2003; pp 237-265.
74. Fukuzumi S, Nakanishi I, Suenobu T and Kadish KM. J. Am. Chem. Soc. 1999; 121: 3468-3474.
75. a) Fukuzumi S, Nakanishi I, Maruta J, Yorisue, T, Suenobu T, Itoh S, Arakawa R and Kadish KM. J. Am. Chem. Soc. 1998; 120: 6673-6680.
76. b) Fukuzumi S, Suenobu T, Patz M, Hirasaka T, Itoh S, Fujitsuka M and Ito O. J. Am. Chem. Soc. 1998; 120: 8060-8068.
77. c) Fukuzumi S, Suenobu T, Hirasaka T, Arakawa R and Kadish KM. J. Am. Chem. Soc. 1998; 120: 9220-9227.
78. Fukuzumi S, Ohkubo K, Imahori H and Guldi DM. Chem. Eur. J. 2003; 9: 1585-1593.
79. a) Kashiwagi Y, Ohkubo K, McDonald JA, Blake IM, Crossley MJ, Araki Y, Ito O, Imahori H and Fukuzumi S. Org. Lett. 2003; 5: 2719-2721.
80. b) Curiel D, Ohkubo K, Reimers JR, Fukuzumi S and Crossley MJ. Phys. Chem. Chem. Phys. 2007; 9: 5260-5266.
81. Scheer H and Inhoffen HH. In The Porphyrins Dolphin D. (Ed.) Academic Press: New York, 1978; Vol II, pp 45-90.
82. a) Hanson LS. In Chlorophylls: Scheer H. (Ed.) CRC Press: Boca Raton, FL, 1991; pp 993-1014.
83. b) Plato M, Möbius K and Lubitz W. In Chlorophylls Scheer, H. (Ed.) CRC Press: Boca Raton, FL, 1991; pp. 1015-1046.
84. a) Fukuzumi S, Ohkubo K, Zheng X, Chen Y, Pandey RK, Zhan R and Kadish KM. J. Phys. Chem. B 2008; 112: 2738-2746.
85. b) Liu C, Dobhal MP, Ethirajan M, Missert JR, Pandey RK, Balasubramanian S, Sukumaran DK, Zhang M, Kadish KM, Ohkubo K and Fukuzumi S. J. Am. Chem. Soc. 2008; 130: in press.
86. Ohkubo K, Chen Y, Pandey RK, Zhan R, Shao J, Kadish KM and Fukuzumi S. J. Phys. Chem. A 2002; 106: 5105-5013.
87. Fukuzumi S and Imahori H. In Electron Transfer in Chemistry Balzani V. (Ed.) Wiley-VCH: Weinheim, 2001; pp 927-975.
88. Guldi DM and Kamat PV. In Fullerenes, Chemistry, Physics, and Technology Kadish KM and Ruoff RS. (Eds.) Wiley-Interscience: New York, 2000, pp 225-281.
89. Sun YP, Riggs JE, Guo Z and Rollins HW. In Optical and Electronic Properties of Fullerenes and Fullerene-Based Materials Shinar J, Vardeny ZV and Kafafi ZH. (Eds.) Marcel Dekker: New York, 2000; pp 43-81.
90. a) Bell TDM, Smith TA, Ghiggino KP, Ranasinghe MG, Shephard MJ and Paddon-Row MN. Chem. Phys. Lett. 1997; 268: 223-228.
91. b) Guldi DM, Luo C, Prato M, Dietel E and Hirsch A. Chem. Commun. 2000; 373-374.
92. a) Hutter MC, Hughes JM, Reimers JR and Hush NS. J. Phys. Chem. B 1999; 103: 4906-4915.
93. b) Harvey SC. Proteins 1989; 5: 78-92.
94. a) Fukuzumi S, Ohkubo K, Suenobu T, Kato K, Fujitsuka M and Ito O. J. Am. Chem. Soc. 2001; 123: 8459-8467.
95. b) Ohkubo K, Suga K, Morikawa K and Fukuzumi S. J. Am. Chem. Soc. 2003; 125: 12850-12859.
96. c) Ohkubo K and Fukuzumi S. Org. Lett. 2000; 2: 3647-3650.
97. a) Ohkubo K, Kotani H and Fukuzumi S. Chem. Commun. 2005; 4520-4522.
98. b) Fukuzumi S, Kotani H and Ohkubo K. Phys. Chem. Chem. Phys. 2008; 10, 5159-5162.
99. a) Fukuzumi S, Ohkubo K, E W, Ou Z, Shao J, Kadish KM, Hutchison JA, Ghiggino KP, Sintic PJ and Crossley MJ. J. Am. Chem. Soc. 2003; 125: 14984-14985.
100. b) Ohkubo K, Sintic PJ, Tkachenko NV, Lemmetyinen H, E W, Ou Z, Shao J, Kadish KM, Crossley MJ and Fukuzumi S. Chem. Phys. 2006; 326: 3-14.
101. a) Kadish KM, E W, Ou Z, Shao J, Sintic PJ, Ohkubo K, Fukuzumi S and Crossley MJ. Inorg. Chem. 2004; 43: 2078-2086.
102. b) Kadish KM, E W, Ou Z, Shao J, Sintic PJ, Ohkubo K, Fukuzumi S and Crossley MJ. Chem. Commun. 2002; 356-357.
103. a) Phthalocyanines: Properties and Applications Leznoff CC and Lever ABP. (Eds.) VCH: Weinheim, 1989, 1993, 1996; Vols. 1-4.
104. b) Hanack M, Heckmann H and Polley R. In Methods in Organic Chemistry (Houben-Weyl) Schumann E. (Ed.) Thieme: Stuttgart: 1998; Vol. E 9d, p 717.
105. c) Rodríguez-Morgade MS. de la Torre G and Torres T. In The Porphyrin Handbook Kadish KM. Smith KM and Guilard R. (Eds.) Academic Press: San Diego, 2003.
106. a) Harriman A, Porter G and M.-C. Richoux, J. Chem. Soc., Faraday Trans. 2 1981; 77: 833-844.
107. b) Vincett PS, Voight EM and Rjeckhoff KE. J. Chem. Phys. 1971; 55: 4131-4140.
108. c) Herkstroeter WG and Merkel PB. J. Photochem. 1981; 16: 331-341
109. a) Martín-Gomis L, Ohkubo K, Fernández-Lázaro F, Sastre-Santos Á and Fukuzumi S. Org. Lett. 2007; 9: 3441-3444.
110. b) Matrín-Gomis L, Ohkubo K, Fernández-Lázaro F, Fukuzumi S and Sastre-Santos Á. J. Phys. Chem. C 2008; 112: in press.
111. a) Würthner F. Chem. Commun. 2004; 1564-1579.
112. b) Langhals H. Helv. Chim. Acta 2005; 88: 1309-1343.
113. c) Wasielewski MR. J. Org. Chem. 2006; 71: 5051-5066.
114. a) Würthner F. Angew. Chem. Int. Ed. 2001; 40: 1037-1039.
115. b) Tan L, Curtis MD and Francis AH. Chem. Mater. 2004; 16: 2134-2141.
116. c) Tatemichi S, Ichikawa M, Koyama T and Taniguchi Y. Appl. Phys. Lett. 2006; 89: 112108.
117. a) Miller MA, Lammi RK, Prathapan S, Holten D and Lindsey JS. J. Org. Chem. 2000; 65: 6634-6649.
118. b) Li X, Sinks LE, Rybtchinski B and Wasielewski MR. J. Am. Chem. Soc. 2004; 126: 10810-10811.
119. a) Rodríguez-Morgade MS, Torres T, Atienza-Castellanos C and Guldi DM. J. Am. Chem. Soc. 2006; 128: 15145-15154.
120. b) Jiménez AJ, Spänig F, Rodríguez-Morgade MS, Ohkubo K, Fukuzumi S, Guldi DM and Torres T. Org. Lett. 2007; 9: 2481-2484.
121. a) Liu MO, Tai C,-H and Hu AT. J. Photochem. Photobiol. A: Chem. 2004; 165: 193-200.
122. b) Gao B, Li Y, Su J and Tian H. Supramol. Chem. 2007; 19: 207-210.
123. c) Chen Y, Lin Y, EI-Khouly ME, Zhuang X, Araki Y, Ito O and Zhang W. J. Phys. Chem. C 2007; 111: 16096-16099.
124. a) You CC and Würthner F. Org. Lett. 2004; 6: 2401-2404.
125. b) Kirmaier C, Yang SI, Prathapan S, Miller MA, Diers JR, Bacian DF, Lindsey JS and Holten D. Res. Chem. Intermed. 2002; 28: 719-740.
126. c) Yang SI, Lammi RK, Prathapan S, Miller MA, Seth J, Diers JR, Bacian DF, Lindsey JS and Holten D. J. Mater. Chem. 2001; 11: 2420-2430.
127. d) Gosztola D, Niemczyk MP and Wasielewski MR. J. Am. Chem. Soc. 1998, 120, 5118-5119.
128. e) Kelley RF, Shin WS, Rybtchinski B, Sinks LE and Wasielewski MR. J. Am. Chem. Soc., 2007; 129: 3173-3181.
129. a) Fukuzumi S. In Electron Transfer in Chemistry Balzani V. (Ed.) Wiley-VCH: Weinheim, 2001; Vol. 4, pp 3-67.
130. b) Fukuzumi S and Itoh S. In Advances in Photochemistry Neckers DC, Volman DH and von Bünau G. (Eds.) Wiley: New York, 1998; Vol. 25, pp 107-172.
131. Fukuzumi S. Org. Biomol. Chem. 2003; 1: 609-620.
132. a) Fukuzumi S, Koumitsu S, Hironaka K and Tanaka T. J. Am. Chem. Soc. 1987; 109: 305-316.
133. b) Fukuzumi S, Nishizawa N and Tanaka, T. J. Chem. Soc., Perkin Trans. 2 1985; 371-378.
134. a) Fukuzumi S, Okamoto T and Otera J. J. Am. Chem. Soc. 1994; 116: 5503-5504.
135. b) Fukuzumi S, Satoh N, Okamoto T, Yasui K, Suenobu T, Seko Y, Fujitsuka M and Ito O. J. Am. Chem. Soc. 2001; 123: 7756-7766.
136. c) Fukuzumi S, Mori H, Imahori H, Suenobu T, Araki Y, Ito O and Kadish KM. J. Am. Chem. Soc. 2001; 123: 12458-12465
137. d) Fukuzumi S, Fujii Y and Suenobu T. J. Am. Chem. Soc. 2001; 123: 10191-10199.
138. a) Fukuzumi S, Ohkubo K and Okamoto T. J. Am. Chem. Soc. 2002; 124: 14147-14155.
139. b) Fukuzumi S, Inada O, Satoh N, Suenobu T and Imahori H. J. Am. Chem. Soc. 2002; 124: 9181-9188.
140. c) Fukuzumi S, Yuasa J and Suenobu T. J. Am. Chem. Soc. 2002; 124: 12566-12573.
141. a) Fukuzumi S, Okamoto K and Imahori H. Angew. Chem. Int. Ed. 2002; 41: 620-622.
142. b) Fukuzumi S, Okamoto K, Yoshida Y, Imahori H, Araki Y and Ito O. J. Am. Chem. Soc. 2003; 125: 1007-1013.
143. a) Fukuzumi S and Ohkubo K. Chem. Eur. J. 2000; 6: 4532-4535.
144. b) Fukuzumi S and Ohkubo K. J. Am. Chem. Soc. 2002; 124: 10270-10271.
145. c) Ohkubo K, Suenobu T, Imahori H, Orita A, Otera J and Fukuzumi S. Chem. Lett. 2001; 978-979
146. a) Fukuzumi, S, Ohkubo K, Ortiz J, Gutiérrez AM, Fernández-Lázaro F and Sastre-Santos Á. Chem. Commun. 2005; 3814-3815.
147. b) Fukuzumi, S, Ohkubo K, Ortiz J, Gutiérrez AM, Fernández-Lázaro F and Sastre-Santos Á. J. Phys. Chem. A 2008; 112: in press.
148. a) Ohkubo K, Ortiz J, Martín-Gomis L, Fernández- Lázaro F, Sastre-Santos Á and Fukuzumi S. Chem. Commun. 2007; 589-591.
149. b) Okamoto K, Mori Y, Yamada H, Imahori H and Fukuzumi S. Chem. Eur. J. 2004; 10: 474-483.