Intramolecular electron transfer of diporphyrins comprised of electron- deficient porphyrin and electron-rich porphyrin with photocontrolled isomerization

Journal of the American Chemical Society

Volumn 121, Issue 1, 1999, Pages 48-53

  Tsuchiya, Shinji ^a  

^a INSTITUTE OF INDUSTRIAL SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZOBENZENE DERIVATIVE; PORPHYRIN DERIVATIVE; ZINC COMPLEX;

ARTICLE; COMPLEX FORMATION; ELECTRONICS; ENERGY TRANSFER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0033550508     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980677a     Document Type: Article

References (82)

1. (a) Wasielewski, M. R. Chem. Rev. 1992, 92, 435.
2. (b) Kureck, H.; Huber, M. Angew. Chem. Int. Ed. Engl. 1995, 34, 849.
3. (c) Ward, M. D. Chem. Soc. Rev. 1997, 26, 365.
4. (d) Cooley, L. F.; Headford, C. E. L.; Elliott, C. M.; Kelley, D. F. J. Am. Chem. Soc. 1988, 110, 6673.
5. (e) Bergkam, M. A.; Dalton, J.; Netzel, T. L. J. Am. Chem. Soc. 1982, 104, 253.
6. (f) McIntosh, A. R.; Ho, T. F.; Bolton, J. R. Nature (London) 1980, 286, 254.
7. Birge, R. R., Ed. Molecular and Biomolecular Electronics: Advances in Chemistry Series 240; American Chemical Society: Washington, DC, 1994.
8. (a) O'Neil, M. P.; Niemczyk, M. P.; Svec, W. A.; Gosztola, D.; Gaines, G. L., III; Wasielewski, M. R. Science 1992, 257, 63.
9. (b) Debreczeny, M. P.; Svec, W. A.; Wasielewsky, M. R. Science 1996, 274, 584.
10. (c) Debreczeny, M. P.; Svec, W. A.; Marsh, E. M.; Wasielewski, M. R. J. Am. Chem. Soc. 1996, 118, 8174.
11. (d) Wiederrecht, G. P.; Svec, W. A.; Wasielewski, M. R. J. Am. Chem. Soc. 1997, 119, 6199.
12. (e) Gosztola, D.; Niemczyk, M. P.; Wasielewski, M. R. J. Am. Chem. Soc. 1998, 120, 5118.
13. (f) Levanon, H.; Galili, T.; Regev, A.; Wiederrecht, G. P.; Svec, W. A.; Wasielewski, J. Am. Chem. Soc. 1998, 120, 6366.
14. (a) Wagner, R. W.; Lindsey, J. S. J. Am. Chem. Soc. 1994, 116, 9759.
15. (b) Crossley, M. J.; Burn, P. L. J. Chem. Soc., Chem. Commun. 1991, 1569.
16. (c) Lin, V. S. Y.; DiMagno, S. G.; Therien, M. T. Science 1994, 264, 1105.
17. (a) Eriksson, S.; Källebring, B.; Larsson, S.; Mårtensson, J.; Wennerström, O. Chem. Phys. 1990, 146, 165.
18. (b) Jaegerman, P.; Plato, M.; van Matzan, B.; Möbius, K. Mol. Phys. 1993, 78, 1057.
19. (a) Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578.
20. (b) Hsiao, J.-S.; Krueger, B. P.; Wagner, R. W.; Delaney, J. K.; Mauzerall, D. C.; Fleming, G. R., Lindsey, J. S.; Bocian, D. F.; Donohoe, R. J. J. Am. Chem. Soc. 1996, 118, 11181.
21. (c) Seth, J.; Palaniappan, V.; Wagner, R. W.; Johnson, T. E.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 11194.
22. (d) Li, F.; Gentemann, S.; Kalsbeck, W. A.; Seth, J.; Lindsey, J. S.; Holten, D.; Bocian, D. F. J. Mater. Chem. 1997, 7, 1245.
23. (e) Strachan, J. P.; Gentemann, S.; Seth, J.; Kalsbeck, W. A.; Lindsey, J. S.; Holten, D.; Bocian, D. F. J. Am. Chem. Soc. 1997, 119, 11191.
24. (f) Strachan, J. P.; Gentemann, S.; Seth, J.; Kalsbeck, W. A.; Lindsey, J. S.; Holten, D.; Bocian, D. F. Inorg. Chem. 1998, 37, 1191.
25. Tsuchiya, S.; Senō, M. Chem. Lett. 1989, 263.
26. Traylor, T. G.; Tsuchiya, S. Inorg. Chem. 1987, 26, 1338.
27. Traylor, T. G.; Tsuchiya, S.; Byun, Y. S.; Kim, C. J. Am. Chem. Soc. 1993, 115, 2775.
28. Traylor, T. G.; Hill, K. W.; Fann, W. P.; Tsuchiya, S.; Dunlap, B. E. J. Am. Chem. Soc. 1992, 114, 1308.
29. Usual porphyrins are known to be decomposed under strong light. When the halogen atoms are substituted directly on the porphyrin ring itself, their properties including redox potentials change greatly. In particular, fluorinated porphyrins are very robust toward oxidizing agents and light.
30. 3) δ = -141.
31. Wijesekera, T.; Matsumoto, A.; Dolphin, D.; Lexa, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 1028.
32. Kadish, K. M.; D'Souza, F.; Villard, A.; Autret, M.; Caemelbecke, E. V.; Bianco, P.; Antonini, A.; Tagliatesta, P. Inorg. Chem. 1994, 33, 5169.
33. (a) Kagan, N. E.; Mauzerall, D.; Merrifield, R. B. J. Am. Chem. Soc. 1977, 99, 5484.
34. (b) Collman, J. P.; Denisevich, P.; Kotani, Y.; Marrocco, M.; Koval, C.; Anson, F. C. J. Am. Chem. Soc. 1980, 102, 6027.
35. (c) Chang, C. K.; Liu, H.-Y.; Abdalmuhdi, I. J. Am. Chem. Soc. 1984, 106, 2725.
36. (d) Hunter, C. A.; Sander, J. K. M.; Stone, A. J. Chem. Phys. 1989, 133, 395.
37. (e) Guilard, R.; Lopez, M. A.; Tabard, A.; Richard, P.; Lecomte, C.; Brandes, S.; Hutchison, J. E.; Collman, J. P. J. Am. Chem. Soc. 1992, 114, 9877.
38. (f) Collman, J. P.; Elliot, C. M.; Halbert, T. R.; Tourog, B. S. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 18.
39. The light with longer wavelength (>440 nm) was cut off by using a Toshiba glass filter (UV-D33S), and then, the region of UV was used for photoirradiation.
40. All of the experiments of photoirradiation were conducted in acetonitrile, because the decomposition of dichloromethane under Xe lamp irradiation was observed.
41. 19
42. Shinkai, S.; Nakaji, T.; Ogawa, T.; Shigematsu, K.; Manabe, O. J. Am. Chem. Soc. 1981, 103, 111.
43. (a) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
44. (b) Barzykin, A. V.; Fox, M. A.; Ushakov, E. N.; Stanislavsky, O. B.; Gromov, S. P.; Fedorova, O. A.; Alfimov, M. V. J. Am. Chem. Soc. 1992, 114, 6381.
45. The decrease (67%) of fluorescence intensity of the trans-isomer of diporphyrin Zn complex 1 for the monomer 5 is caused from the interaction via the azobenzene linker, while for the cis-isomer, the larger decrease (80%) of fluorescence intensity for the monomer 5 would arise from direct interaction between two porphyrin Zn complexes.
46. The relative fluorescence intensities of diporphyrin Zn complexes with other β-halogen atoms were measured for comparison purposes. The relative intensities of the cis-isomers of β-brominated diporphyrin Zn complex 16 and β-chlorinated diporphyrin Zn complex 17 were 0.79 and 0.73, respectively. The ratios of fluorescence quenching of these diporphyrin Zn complexes (16, 17) are smaller, suggesting that the electron-transfer interaction may be controlled by both steric and electronic factors of β-halogen atoms on one porphyrin ring. The synthetic methods of Zn complexes (16, 17) were described in the Experimental Section.
47. When the large overlap between the absorption of UV-visible spectrum and the absorption of fluorescence spectrum exists, there is the possibility that the intramolecular energy transfer occurs.
48. Groves, J. T.; Watanabe, Y. J. Am. Chem. Soc. 1988, 110, 8443.
49. (a) Fajer, J.; Borg, D. C.; Forman, A.; Dolphin, D.; Felton, R. H. J. Am. Chem. Soc. 1970, 92, 3451.
50. (b) Closs, G. L.; Closs, L. E. J. Am. Chem. Soc. 1963, 85, 818.
51. (c) Dolphin, D., Ed. The Porphyrins; Academic Press: New York, 1978.
52. Tsuchiya, S. J. Chem. Soc., Chem. Commun. 1991, 716.
53. 3f.25a,26.28 This broadening is probably due to intramolecular dipolar-dipolar and exchange interaction among the radicals.
54. Mitomo, S.; Tsuchiya, S.; Senō, M.; Tokita, S. Mol. Cryst. Liq. Cryst. 1998, 312, 263.
55. (a) Grinstaff, M. W.; Hill, M. G.; Labinger, J. A.; Gray, H. B. Science 1994, 246, 1311.
56. (b) Takeuchi, T.; Gray, H. B.; Goddard, W. A., III, J. Am. Chem. Soc. 1994, 116, 1311.
57. (c) Birbaum, E. R.; Schaefer, W. P.; Labinger, J. A.; Bercaw, J. E.; Gray, H. B. Inorg. Chem. 1995, 34, 1751.
58. (d) Hoffman, P.; Meunier, B. New J. Chem. 1992, 16, 559.
59. (e) Meunier, B. Chem. Rev. 1992, 92, 1411.
60. (f) Lyons, J. E.; Ellis, P. E., Jr. Catal. Chem. 1991, 8, 45.
61. (g) D'Souza, F.; Villard, A.; Caemelbecke, E. V.; Franzen, M.; Boschi, T.; Tagliatesta, P.; Kadish, K. M. Inorg. Chem. 1993, 32, 4042.
62. (h) Sheldon, R. A., Ed. Metalloporphyrins in Catalytic Oxidations; Marcel Dekker: New York, 1994.
63. Ochsenbein, P.; Mandon, D.; Fischer, J.; Weiss, R.; Austin, R.; Jayaraj, K.; Gold, A.; Temer, J.; Bill, E.; Muther, M.; Trautwein, A. X. Angew. Chem., Int. Ed. Engl. 1993, 32, 1437.
64. (j) Mandon, D.; Ochsenbein, P.; Fischer, J.; Weiss, R.; Jayaraj, K.; Austin, R. N.; Gold, A.; White, P. S.; Brigaud, O.; Battioni, P.; Mansuy, D. Inorg. Chem. 1992, 31, 2044.
65. (k) Bartoli, J. F.; Brigaud, O.; Battioni, P.; Mansuy, D. J. Chem. Soc., Chem. Commun. 1991, 440.
66. Dolphin, D.; Traylor, T. G.; Xie, L. Y. Acc. Chem. Res. 1997, 30, 251.
67. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 3996.
68. (a) Huck, N. P. J. M.; Feringa, B. L. J. Chem. Soc., Chem. Commun. 1995, 1095.
69. (b) Goulle, V.; Harrimen, A.; Lehn, J. M. J. Chem. Soc., Chem. Commun. 1993, 1034.
70. (a) Fabbrizzi, L.; Zpoggi, A. Chem. Soc. Rev. 1995, 197.
71. (b) Bissell, R. A.; de Silva, A. P.; Gunaratne, H. Q. N.; Lynch, P. L. M.; Maguire, G. E. M.; Sandanayake, K. R. A. S. Chem. Soc. Rev. 1992, 187.
72. (c) Knorr, A.; Daub, J. Angew. Chem. Int. Ed. Engl. 1995, 34, 2664.
73. Winter, G. Inorg. Synth. 1973, 14, 101.
74. The relative fluorescence quantum yields of compounds (1, 2, 5, and 9) were summarized in Table 3. The measurements of the relative fluorescence quantum yields of other diporphyrin Zn complexes and diporphyrins have been tried by using several methods (Ogawa, S.; Tsuchiya, S. Chem. Lett. 1996, 709). The results of these measurements will be published in the future.
75. Dolphin, D., Ed. The Porphyrins, III; Academic Press: New York, 1978.
76. Hill, C. L.; Williamson, M. M. J. Chem. Soc., Chem. Commun. 1985, 1228.
77. Tsuchiya, S.; Senō, M.; Kawai, M. Jpn. Kokai Tokkyo Koho JP 02250883. (Chem. Abstr. 1991, 115, 79933f). Tsuchiya, S.; Senō, M. Chem. Lett. 1989, 263.
78. Tsuchiya, S.; Senō, M.; Kawai, M. Jpn. Kokai Tokkyo Koho JP 02250883. (Chem. Abstr. 1991, 115, 79933f). Tsuchiya, S.; Senō, M. Chem. Lett. 1989, 263.
79. 60 porphyrin = superteflon porphyrin) is expected to have this excellent property; the synthesis of diporphyrin containing this dodecaarylporphyrin is in progress.
80. 60 porphyrin = superteflon porphyrin) is expected to have this excellent property; the synthesis of diporphyrin containing this dodecaarylporphyrin is in progress.
81. 60 porphyrin = superteflon porphyrin) is expected to have this excellent property; the synthesis of diporphyrin containing this dodecaarylporphyrin is in progress.
82. -1. The syntheses of Zn complexes (18, 19) of tetrakisphenylporphyrin dimer with an azo linkage at the 2′ or 4′ positions of the phenyl moiety at the meso position were conducted, and similar values of v(NN) were obtained. Diporphyrin Zn complexes (3, 16, 17) gave satisfactory elemental analyses for C, H, and N and parent peaks in the mass spectrum in agreement with the calculated values.