Excited-State Energy Transfer Processes in Phenylene- And Biphenylene-Linked and Directly-Linked Zinc(II) and Free-Base Hybrid Diporphyrins

Journal of Physical Chemistry A

Volumn 105, Issue 17, 2001, Pages 4200-4210

  Sun Cho, Hyun ^a   Jeong, Dae Hong ^b   Yoon, Min Chul ^c   Kim, Yong Hee ^d   Kim, Yong Rok ^c   Kim, Dongho ^a   Jeoung, Sae Chae ^a   Kim, Seong Keun ^c   Aratani, Naoki ^a   Shinmori, Hideyuki ^b   Osuka, Atsuhiro ^a  

^a Yonsei University   (South Korea)

^b Korea Research Institute of Standards and Science   (South Korea)

^c Seoul National University   (South Korea)

^d KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOINDUCED ENERGY TRANSFER PROCESSES;

ABSORPTION SPECTROSCOPY; CHEMICAL BONDS; DIMERS; ELECTRONIC STRUCTURE; ELECTROSTATICS; ENERGY TRANSFER; PHOTOCHEMICAL REACTIONS; RATE CONSTANTS; SUBSTITUTION REACTIONS;

PORPHYRINS;

EID: 0035799966     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp010385n     Document Type: Article

References (83)

1. (a) Wasielewski, M. R. Chem. Rev. 1992, 94, 435.
2. (b) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198.
3. Speiser, S. Chem. Rev. 1996,96,1953.
4. Chou, J.; Kosal, M. E; Nalwa, H. S.; Rakow, N. A.; Suslick, K. S. In The Porphyrin Handbook; Radish, K. M.; Smith, K. M.; Guilard, R. Eds.; Academic Press: New York, 2000; Vol. 6, p. 43.
5. (a) Wagner, R. W.; Lindsey, J. S.J. Am. Chem. Soc. 1994, 116, 9759.
6. (b) Prathapan, S.; Johnson, T. E.; Lindsey, J. S. J. Am. Chem. Soc. 1993, 775, 7519.
7. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 3996.
8. (a) Gosztola, D.; Yamada, H.; Wasielewski, M. RJ. Am. Chem. Soc. 1995,117, 2041.
9. (b) Debreczeny, M. P.; Svec, W. A.; Marsh, E. M.; Wasielewski, M. R. J. Am. Chem. Soc. 1996, 118, 8174.
10. Debreczeny, M. P.; Svec, W. A.; Wasielewski, M. R. Science 1996, 274, 584.
11. (a) Lin, V. S.-Y.; DiMagno, S. G.; Therien, M. J. Science 1994, 264, 1105.
12. (b) Lin, V. S.-Y.; Therien, M. J. Chem.-Eur. J. 1995, 1, 645.
13. (a) Arnold, D. P.; Nitschinsk, L. J. Tetrahedron 1992, 48, 8781.
14. (b) Arnold, D. P.; Heath, G. A.; James, D. A. J. For. Phthl 1999, 3, 5.
15. Anderson, H. L. Inorg. Chem. 1994, 33, 972.
16. Anderson, H. L. Chem. Commun. 1999, 2323.
17. (a) Vicente, M. G. H.; Smith, K. M. J. Org. Chem. 1991,56,4407.
18. (b) Vicente, M. G. H.; Jaquinod, L.; Smith, K. M. Chem. Commun. 1999, 1771.
19. (a) Burrell, A. K.; Officer, D. L.; Reid, D. C. W. Angew. Chem., Int. Ed. Engl. 1995,34, 900.
20. (b) Burrell, A. K.; Officer, D. L. Synlelt. 1998, 1297.
21. (a) Osuka, A.; Liu, B.-L.; Mamyama, K. Chem. Lett. 1993, 949.
22. (b) Osuka, A.; Maruyama, K.; Malaga, N.; Asahi, T.; Yamazaki, I.; Tamai, N. J. Am. .Chem. Soc. 1990, 112, 4958.
23. Osuka, A.; Nakajima, S.; Maruyama, K.; Malaga, N.; Asahi, T.; Yamazaki, I.; Nishimura, Y.; Ohno, T.; Nozaki, K. J. Am. Chem. Soc. 1993, 115, 4577.
24. Osuka, A.; Maruyama, K. J. Am. Chem. Soc. 1988, 110, 4454.
25. (e) Osuka, A.; Maruyama, K.; Yamazaki, I.; Tamai, N. J. Chem. Soc., Chem. Commun. 1988, 1243.
26. (f) Osuka, A.; Maruyama, K.; Yamazaki, I.; Tamai, N. Chem. Phys. Lett. 1990, 165, 392.
27. (a) Ponomarev, G. V.; Borovkov, V.; Sugiura, K.; Sakata, Y.; Shul'ga, A. Tetrahedron Lett. 1993, 34, 2153.
28. (b) Senge, M. O.; Gerzevske, K.; Vicente, M. G. H.; Forsyth, T.; Smith, K. M. Angew. Chem., Int. Ed. Engl. 1993, 32, 750.
29. Higuchi, H.; Takeuchi, M.; Ojima, J. Chem. Lett. 1996, 593.
30. Sugiura, K.; Tanaka, H.; Matsumoto, T.; Kavvai, T.; Sakata, Y. Chem. Lett. 1999, 1193.
31. (a) Sessler, J. L.; Johnson, M. R. Angew: Chem., Int. Ed. Engl. 1987, 26,678.
32. (b) Sessler, J. L.; Capuano, V. L.; Harriman, A. J. Am. Chem. Soc. 1993,115, 4618.
33. Brun, A. M.; Harriman, A.; Heitz, V.; Sauvase, J.-P. J. Am. Chem. Soc. 1991, 113, 8657.
34. Härberle, T.; Hirsch, J.; Pöllinger, F.; Heitele, H.; Michel-Beyerle, M. E.; Anders, C.; Döhling, A.; Krieger, C.; Rückemann, A.; Staab, H. A. J. Phys. Chem. 1996,100, 18269.
35. (e) Staab, H. A.; Carell, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1466.
36. (a) Förster, T. Ann. Phys. 1948, 2, 55
37. (b) Förster, T. Discuss. Faraday Soc. 1959, 27, 7.
38. Dexter, D. L. J. Chem. Phys. 1953, 21, 836.
39. van Grondelle, R.; Dekker: J. P.; Gillbro, T.; Sundström, V. Biochim. Biophys. Acta 1994, 1187, 1.
40. Gillbro, T.; Sharkov, A. V.;-Kryukov, I. V.; Khoroshilov, E. V.; Kryukov, P. G.; Fischer, R.; Scheer. H. Biochim. Biophys. Acta 1993,1140, 321.
41. (a) Breton, J.; Martin, J.-L.; Migus, A.; Antonetti, A.; Orszag, A. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 5121.
42. (b) Jia, Y.; Jonas, D. M.; Joo, T.; Nagasawa, Y.; Lang, M. J.; Fleming, G. R. J. Phys. Chem. 1995, 99,6263.
43. (a) McDermott, G. M.; Prince, S. M.; Freer, A. A.; Lawless, A. H. H.; Papiz, M. Z.; Cogdell, R. J.; Isaacs, N. W. Nature 1995, 374, 517.
44. (b) Koepke, J.; Hu, X.; Muenke, C.; Schulten, K.; Michel, H. Structure 1996, 4,581.
45. Pullerits, T.; Sundström, V. Ace. Chem. Res. 1996,29, 381.
46. Sundström, V.; Pullerits, T.; van .Grondelle, R. J. Phys. Chem. B 1999, 103, 2327.
47. (e) van Oijen, A. M.; Ketelaars, M.; Köhler, J.; Aartsma, T. J.; Schmidt, J. Science 1999, 285, 400.
48. Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, L; Nishimura, Y. J. Org. Chem. 1995, 60, 7177.
49. (a) Strachan, J. P.; Gentemann, S.; Seth, J.; Kalsbeck, W. A.; Lindsey, J. S.; Holten, D.; Bocian, D. F. J. Am. Chem. Soc. 1997, 779, 11191.
50. (b) Yang, S. L; Seth, J.; Balasubramanian, T.; Kim, D.; Lindsey, J. S.; Holten, D.; Bocian, D. F. J. Am. Chem. Soc. 1999, 727, 4008.
51. (a) Kawabata, S.; Yamazaki, 1.; Nishimura, Y.; Osuka, A. J. Chem. Soc., Perkin Trans 2 1997, 479.Weite
52. (b) Osuka, A.; Ikeda, M.; Shiratori, H.; Nishimura, Y.; Yamazaki, I. J. Chem. Soc., Perkin Trans. 2 1999, 1019.
53. (a) Jensen, K. K.; van Berlekom, S. B.; Kajanus, K.; Martensson, J.; Albinsson, B. J. Phys. Chem. 1997, 101, 2218.
54. (b) Kilsa, K.; Kajanus, J.; Martensson, J.; Albinsson, B. J. Phys. Chem. B 1999, 103, 7329.
55. Brodard, P.; Matzinser, S.; Vauthey, E.; Monsin, O.; Papamicael, C; Gossauer, A. J. Phys. Chem. A 1999, 103, 58587
56. (a) Hofmann, E.; Wrench, P. M.; Sharpies, F. P.; Hiller, R. G.; Weite, W.; Diederichs, K. Science 1996, 272, 1788.
57. (b) Krueger, B. P.; Scholes, G. D.; Jimenez, R.; Flemina, G. R. J. Phys. Chem. 1998, 702, 2284.
58. Debreczeny, M. P.; Wasielewski, M. R.; Shinoda, S.; Osuka, A. J. Am. Chem. Soc. 1997, 119, 6401.
59. 1,2-Phenylene-bridged TPP-type diporphyrin was first prepared by Kobuke et al., but its mono-zinc complex was not reported. Meier, H.; Kobuke, Y.; Kugimiya, S. J. Chem. Soc., Chem. Commun. 1989, 923.
60. 1,3-PhenyIene-bridged TPP-type diporphyrin was reported by Tabushi et al.:
61. (a) Tabushi, I.; Sasaki, T. Tetrahedron Lett. 1982, 23, 1913.
62. (b) Tabushi, I.; Sasaki, T. J. Am. Chem. Soc. 1983, 705, 2901. Preliminary results on intramolecular energy transfer were reported in ref 23 and the following paper: Meier, H.; Kobuke, Y.; Kueimiya, S. Tetrahedron Lett. 1989, 30, 5301.
63. 1,4-Phenylene-bridged TPP-type diporphyrin was first reported: (a) Wennerstrom, O.; Ericsson, H.; Raston, I.; Svensson, S.; Pimlott, W. Tetrahedron Lett. 1989, 30, 1129. Intramolecular energy transfer in 1,4phenylene-bridged TPP-type Zn(II)-free base hybrid diporphyrin was reported:
64. (b) Yang, S. I.; Lammi, R. K.; Seth, J.; Riggs, J. A.; Arai, T.; Kim, D.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Phys. Chem. B 1998, 102, 9426.
65. 1,2-Phenylene-bridged OEP-type diporphyrin was prepared: Osuka, A.; Nakajima, S.; Nagata, T.; Maruyama, K.; Toriumi, K. Angew. Chem., Int. Ed. Engl. 1991, 30, 582.
66. 1,3-Phenylene-bridged OEP-type diporphyrin was reported:
67. (a) Sessler, J. L.; Hugdahl, J.; Johnson, M. R. J. Org. Chem. 1986, 57, 2838. Osuka, A.; Maruyama, K. J. Am. Chem. Soc. 1988, 770, 4454. Intramolecular energy transfer in Zn(II)-free base hybrid diporphyrins was reported in:
68. (b) Rodriguez, J.; Krimaier, C.; Johnson, M. R.; Friesner, R. A.; Holten, D.; Sessler, J. L. J. Am. Chem. Soc. 1991, 77.?, 1652, and ref 8f.
69. 1,4-Phenylene bridged OEP-type diporphyrin was reported in ref 9a and the intramolecular energy transfer in Zn(II)-free base hybrid diporphyrin was reported in refs 8f and 27b.
70. (a) Osuka, A.; Shimidzu, H.; Angew. Chem., Int. Ed. Engl. 1997, 36, 135.
71. (b) Aratani, N.; Osuka, A.; Kim, Y. H.; Jeong, D. H.; Kim, D. Angm. Chem., Int. Ed. Engl. 2000, 39, 1458.
72. (a) Kasha, M. Radiation Res. 1963, 20,55.
73. (b) Kasha, M.; Rawls, H. R.; El-Bayoumi, M. A. Pure Appl. Chem. 1965, 77, 371.
74. (a) Gouterman, M. In Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. III, pp 1-165.
75. (b) Spellane, J. P.; Gouterman, M.; Antipas, A.; Kim, S.; Liu, Y. C. Inorg. Chem. 1980, 79, 386.
76. Fujii, H. Chem. Lett. 1994, 1491.
77. 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.
78. Nasae, H.; Kakitani, T.; Mimuro, M. J. Chem. Phys. 1993, 98, 8012.
79. (a) Kakitani, T.; Kimura, A.; Sumi, H. J. Phys. Chem. B 1999, 703, 3720.
80. (b) Kimura, A.; Kakitani, T.; Yamato, T. submitted to J. Phys. Chem.
81. (a) Zimmerman, H. E.; McKelvey, R. D. J. Am. Chem. Soc. 1971, 93,3638.
82. (b) Oevering, H.; Verhoeven, J. W.; Paddon-Row: M. R; Cotsaris, E.; Hush, N. S. Chem. Phys. Lett. 1988,143,488.
83. Harriman, A.; Ziessel, R. Chem. Commun. 1996, 1707.