Formation of a supramolecular porphyrin-spacer-acceptor ternary complex and intracomplex electron transfer

Journal of Physical Chemistry A

Volumn 107, Issue 3, 2003, Pages 379-385

  Otsuki, Joe ^a   Takatsuki, Masayuki ^a   Kaneko, Motomu ^a   Miwa, Hironari ^a   Takido, Toshio ^a   Seno, Manabu ^a   Okamoto, Ken ^b,c   Imahori, Hiroshi ^b,c,e   Fujitsuka, Mamoru ^d   Araki, Yasuyuki ^d   Ito, Osamu ^d   Fukuzumi, Shunichi ^b  

^a NIHON UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^d TOHOKU UNIVERSITY   (Japan)

^e KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ASSOCIATION REACTIONS; CHARGE TRANSFER; COORDINATION REACTIONS; ELECTRONS; FLUORESCENCE; METHANE; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMICAL REACTIONS; RATE CONSTANTS;

ASSOCIATION CONSTANT; DICHLOROMETHANE; FLUORESCENCE QUENCHING; INTRACOMPLEX ELECTRON TRANSFER; N PROPYLISONICOTAMIDINE; PHOTOINDUCED INTRACOMPLEX ELECTRON TRANSFER; ZINC TETRAPHENYLPORPHYRIN;

PORPHYRINS;

EID: 0037461692     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp027165+     Document Type: Article

References (83)

1. (a) Meyer, T. J. Acc. Chem. Res. 1989, 22, 163-170.
2. (b) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205.
3. (c) Gust, D.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40-48.
4. (d) Paddon-Row: M. N. Acc. Chem. Res. 1994, 27, 18-25.
5. (e) Verhoeven, J. W. Adv. Chem. Phys. 1999, 166, 603-644.
6. (a) Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461.
7. (b) Maruyama, K.; Osuka, A. Pure Appl. Chem. 1990, 62, 1511-1520.
8. (c) Guldi, D.; Prato, M. Acc. Chem. Res. 2000, 33, 695-703.
9. (d) Imahori, H.; Sakata, Y. Eur. J. Org. Chem. 1999, 2445-2457.
10. (a) Blanco, M.J.; Jiménez, M. C.; Chambron, J.-C.; Heitz, V.; Linke, M.; Sauvage, J.-P. Chem. Soc. Rev. 1999, 293-305.
11. (b) Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
12. (a) Hayashi, T.; Ogoshi, H. Chem. Soc. Rev. 1997, 26, 355-364.
13. (b) Ward, M. D. Chem. Soc. Rev. 1997, 26, 365-375.
14. (a) Gonzalez, M. C.; McIntosh, A. R.; Bolton, J. R.; Weedon, A. C. J. Chem. Soc., Chem. Commun. 1984, 1138-1140.
15. (b) Kuroda, Y.; Ito, M.; Sera, T.; Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 7003-7004.
16. (a) Gunter, M. J.; Johnston, M. R. J. Chem. Soc., Perkin Trans. 1 1994, 995-1008.
17. (b) Dürr, H.; Bossmann, S.; Schwarz, R.; Kropf, M.; Hayo, R.; Turro, N. J. J. Photochem. Photobiol. A 1994, 80, 341-350.
18. (c) Kaganer, E.; Joselevich, E.; Willner, I.; Chen, Z.; Gunter, M. J.; Gayness, T. P.; Johnson, M. R. J. Phys. Chem. B 1998, 102, 1159-1165.
19. (a) Hofstra, U.; Koehorst, R. B. M.; Schaafsma, T. J. Chem. Phys. Lett. 1986, 130, 555-559.
20. (b) Hugerat, M.; Levanon, H.; Ojadi, E.; Biczok, L.; Linschitz, H. Chem. Phys. Lett. 1991, 181, 400-406.
21. (c) Hayashi, T.; Takimura, T.; Ogoshi, H. J. Am. Chem. Soc. 1995, 117, 11606-11607.
22. (d) Berg, A.; Rachamim, M.; Galili, T.; Levanon, H. J. Phys. Chem. 1996, 100, 8791-8795.
23. (a) Anderson, H. L.; Hunter, C. A.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1989, 226-227.
24. (b) Hunter, C. A.; Sanders, J. K. M.; Beddard, G. S.; Evans, S.; J. Chem. Soc., Chem. Commun. 1989, 1765-1767.
25. (c) Rempel, U.; von Maltzan, B.; von Borczyskowski, C. Pure Appl. Chem. 1993, 65, 1681-1685.
26. (d) Imahori, H.; Yoshizawa, E.; Yamada, K.; Hagiwara, K.; Okada, T.; Sakata, Y. J. Chem. Soc., Chem. Commun. 1995, 1133-1134.
27. (e) Hunter, C. A.; Hyde, R. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1936-1939.
28. Otsuki, J.; Harada, K.; Toyama, K.; Hirose, Y.; Araki, K.; Seno, M.; Takatera, K.; Watanabe, T. Chem. Commun. 1998, 1515-1516.
29. (a) Da Ros, T.; Prato, M.; Guldi, D.; Alessio, E.; Ruzzi, M.; Pasimeni, L. Chem. Commun. 1999, 635-636.
30. (b) Yamada, K.; Imahori, H.; Yoshizawa, E.; Gosztola, D.; Wasielewski, M. R.; Sakata, Y. Chem. Lett. 1999, 235-236.
31. (c) D'Souza, F.; Deviprasad, G. R.; Rahman, M. S.; Choi, J.-P. Inorg. Chem. 1999, 38, 2157-2160.
32. (d) Armaroli, N.; Diederich, F.; Echegoyen, L.; Habicher, T.; Flamigni, L.; Marconi, G.; Nierengarten, J. F. New J. Chem. 1999, 23, 77-83.
33. (e) Flamigni, L.; Johnston, M. R.; Giribabu, L. Chem. Eur. J. 2002, 8, 3938-3947.
34. (a) Guldi, D. M. Chem. Commun. 2000, 321-327.
35. (l) Guldi, D. M.; Luo, C.; Da Ross, T.; Prato, M.; Dietel, E.; Hirsch, A.; Chem. Commun. 2000, 375-376.
36. (b) D'Souza F.; Rath, N. P.; Deviprasad, G. R.; Zandler, M. E. Chem. Commun. 2001, 267-268.
37. (c) Da Ros, T.; Prato, M.; Guldi, D. M.; Ruzzi, M.; Pasimeni, L. Chem. Eur. J. 2001, 7, 816-827.
38. (a) Brun, A. M.; Atherton, S. J.; Harriman, A.; Heitz, V.; Sauvage, J. P. J. Am. Chem. Soc. 1992, 114, 4632-4639.
39. (b) Chambron, J.-C.; Chardon-Noblat, S.; Harriman, A.; Heitz, V.; Sauvage, J.-P. Pure Appl. Chem. 1993, 65, 2343-2349.
40. (a) Aoyama, Y.; Asakawa, M.; Matsui, Y.; Ogoshi, H. J. Am. Chem. Soc. 1991, 113, 6233.
41. (b) Harriman, A.; Kubo, Y.; Sessler, J. L. J. Am. Chem. Soc. 1992, 114, 388-390.
42. Turró, C.; Chang, C. K.; Leroi, G. E.; Cukier, R. I.; Nocera, D. G. J. Am. Chem. Soc. 1992, 114, 4013-4015.
43. (a) Hayashi, T.; Miyahara, T.; Hashizume, N.; Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 2049-2051.
44. (b) Sessler, J. L.; Wang, B.; Harriman, A. J. Am. Chem. Soc. 1993, 115, 10418-10419.
45. (c) Cukier, R. I. J. Phys. Chem. 1994, 98, 2377-2381.
46. (d) Shafirovich, V. Y.; Courtney, S. H.; Ya, N.; Geacintov, N. E. J. Am. Chem. Soc. 1995, 117, 4920-4929.
47. (a) Berman, A.; Izraeli, E. S.; Levanon, H.; Wang, B.; Sessler, J. L. J. Am. Chem. Soc. 1995, 117, 8252-8257.
48. (b) de Rege, P. J. F.; Williams, S. A.; Therien, M. J. Science 1995, 269, 1409-1413.
49. (c) Hayashi, T.; Miyahara, T.; Kumazaki, S.; Ogoshi, H.; Yoshihara, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1964-1965.
50. (d) Arimura, T.; Brown, C. T.; Springs, S. L.; Sessler, J. L. Chem. Commun. 1996, 2293-2294.
51. (a) D'Souza, F. J. Am. Chem. Soc. 1996, 118, 923-924.
52. (b) Osuka, A.; Yoneshima, R.; Shiratori, H.; Okada, T.; Taniguchi, S.; Mataga, N. Chem. Commun. 1998, 1567-1568.
53. (c) Berg, A.; Schuali, Z.; Asano-Someda, M.; Levanon, H.; Fuhs, M.; Möbius, K.; Wang, R.; Brown, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 7433-7434.
54. (d) Ghaddar, T. H.; Castner, E. W.; Isied, S. S. J. Am. Chem. Soc. 2000, 122, 1233-1234.
55. (e) Myles, A. J.; Branda, N. R. J. Am. Chem. Soc. 2001, 123, 177-178.
56. (f) Smitha, M. A.; Prasad, E.; Gopidas, K. R. J. Am. Chem. Soc. 2001, 123, 1159-1165.
57. (a) Roberts, J. A.; Kirby, J. P.; Nocera, D. G. J. Am. Chem. Soc. 1995, 117, 8051-8052.
58. (b) Cukier, R. I. J. Phys. Chem. 1996, 100, 15428-15443.
59. (c) Kirby, J. P.; Roberts, J. A.; Nocera, D. G. J. Am. Chem. Soc. 1997, 119, 9230-9236.
60. (d) Soudackov, A.; Hammes-Schiffer, S. J. Am. Chem. Soc. 1999, 121, 10598-10607.
61. (a) Kirby, J. P.; van Dantzig, N. A.; Chang, C. K.; Nocera, D. G. Tetrahedron Lett. 1995, 20, 3477-3480.
62. (b) Deng, Y.; Roberts, J. A.; Peng, S.-M.; Chang, C. K.; Nocera, D. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2124-2127.
63. (a) Seiler, M.; Dürr, H.; Willner, I.; Joselevich, E.; Doron, A.; Stoddart, J. F. J. Am. Chem. Soc. 1994, 116, 3399-3404.
64. (b) Kropf, M.; Joselevich, E.; Dürr, H.; Willner, I. J. Am. Chem. Soc. 1996, 118, 655-665.
65. (c) David, E.; Born, R.; Kaganer, E.; Joselevich, E.; Dürr, H.; Willner, I. J. Am. Chem. Soc. 1997, 119, 7778-7790.
66. (d) Linke, M.; Chambron, J.-C.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1997, 119, 11329-11330.
67. (e) Hu, Y.-Z.; van Loyen, D.; Schwarz, O.; Bossmann, S.; Dürr, H.; Huch, V.; Veith, M. J. Am. Chem. Soc. 1998, 120, 5822-5823.
68. Hunter, C. A.; Shannon, R. J. Chem. Commun. 1996, 1361-1362.
69. D'Souza, F.; Deviprasad, G. R.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O. J. Am. Chem. Soc. 2001, 123, 5277-5284.
70. (a) Abraham, R. J.; Bedford, G. R.; McNeillie, D.; Write, B.; Org. Magn. Reson. 1980, 14, 418-425.
71. (b) Chachaty, C.; Gust, D.; Moore, T. A.: Nemeth, G. A.; Liddell, P. A.; Moore, A. L. Org. Magn. Reson. 184, 22, 39-46.
72. Jorgensen, W. L.; Pranata, J. J. Am. Chem. Soc. 1990, 112, 2008-2010.
73. Otsuki, J.; Chiang, L C.; Lee, S. H.; Araki, K.; Seno, M. Supramol. Chem. 1993, 2, 25-31.
74. Collins, D. M.; Hoard, J. L. J. Am. Chem. Soc. 1970, 92, 3761-3771.
75. Nappa, M.; Valentine, J. S. J. Am. Chem. Soc. 1978, 100, 5075-5080.
76. lZnTPP* to DNBA in the ternary complex in dichloromethane was too fast to be detected by the time-resolved fluorescence measurements probably due to the smaller solvent reorganization energy of electron transfer as compared to the case in a more polar solvent, acetonitrile. The decomposition of ZnTPP in dichloromethane induced by picosecond laser pulses has precluded the picosecond time scale measurements of transient absorption spectra of ZnTPP·1·DNBA in this solvent.
77. Imahori, H.; Yamada, K.; Yoshizawa, E.; Hagiwara, K.; Okada, T.; Sakata, Y. J. Porphyrins Phthalocyanines 1997, 1, 55-66. The Coulombic terms in the complex are negligible, especially in solvents with moderate or high polarity, because of the relatively large donor-acceptor distance (15 Å).
78. Luo, C.; Guldi, D. M.; Imahori, H.; Tamaki, K. Sakata, Y. J. Am. Chem. Soc. 2000, 122, 6535-6551.
79. 1 value of the coordinated ZnTPP was obtained from the phosphorescence of ZnTPP·EtPy in 2-methyltetrahydrofuran at 77 K.
80. -1, which is within a range of typical diffusion-controlled reactions.
81. Hand, E. S.; Jencks, W. P. J. Am. Chem. Soc. 1962, 84, 3505-3514.
82. Dox, A. W. In Organic Synthesis, Coll. vol. 1; Gilman, H., Blatt, A. H., Eds.: John Wiley and Sons: New York, 1941; p 5-7.
83. Singh, B.; Lesher, G. Y. J. Heterocycl. Chem. 1977, 14, 1413-1414.