Electron transfer in a hydrogen-bonded assembly consisting of porphyrin–diimide

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Atsuhiro Osuka, Ryusho Yoneshima, Hideo Shiratori, Atsuhiro Osuka, Tadashi Okada, Seiji Taniguchi and Noboru Mataga


Abstract

Electron-transfer reactions in an H-bonded assembly composed of a diacylaminopyridine bearing zinc porphyrin and 1,8:4,5-naphthalenetetracarboxylic diimide (Ka = 2.8 × 102 dm3 mol1) in benzene occur with kCS = 4.1 × 1010 s1 and kCR = 3.7 × 109 s1, while the corresponding covalently linked model with a comparable distance and energy gap undergoes electron transfer with kCS = 9.9 × 1010 s1 and kCR = 6.7 × 108 s1.


References

  1. Y. Aoyama, M. Asakawa, Y. Matsui and H. Ogoshi, J. Am. Chem. Soc., 1991, 113, 6233 CrossRef CAS; T. Hayashi, T. Miyahara, N. Hashizume and H. Ogoshi, J. Am. Chem. Soc., 1993, 115, 2049 CrossRef CAS.
  2. A. Harriman, Y. Kubo and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 388 CrossRef CAS; T. Arimura, C. T. Brown, S. L. Springs and J. L. Sessler, Chem. Commun., 1996, 2293 RSC.
  3. (a) C. Turro, C. K. Chang, G. E. Leroi, R. I. Cukier and D. G. Nocera, J. Am. Chem. Soc., 1992, 114, 4013 CrossRef CAS; (b) T. Hayashi, T. Miyahara, S. Kumazaki, H. Ogoshi and K. Yoshihara, Angew. Chem., Int. Ed. Engl., 1996, 35, 1964 CrossRef CAS.
  4. J. P. Kirby, N. A. van Dantzig, C. K. Chang and D. G. Nocera, Tetrahedron Lett., 1995, 36, 3477 CrossRef CAS; J. A. Roberts, J. P. Kirby and D. G. Nocera, J. Am. Chem. Soc., 1995, 117, 8051 CrossRef CAS; J. P. Kirby, J. A. Roberts and D. G. Nocera, J. Am. Chem. Soc., 1997, 119, 9230 CrossRef CAS; Y. Deng, J. A. Roberts, S.-M. Peng, C. K. Chang and D. Nocera, Angew. Chem., Int. Ed. Engl., 1997, 36, 2124 CrossRef CAS.
  5. P. J. F. de Rege, S. A. Williams and M. J. Therien, Science, 1995, 269, 1409 CAS.
  6. A. Osuka, H. Shiratori, R. Yoneshima, T. Okada, S. Taniguchi and N. Mataga, Chem. Lett., 1995, 913 CAS.
  7. H. Miyasaka, A. Tabane, K. Kamada and N. Mataga, J. Am. Chem. Soc., 1993, 115, 7335 CrossRef CAS and references therein.
  8. A. D. Hamilton, N. Pant and A. Muehldorf, Pure Appl. Chem., 1988, 60, 535; M. Kotera, J.-M. Lehn and J. P. Vigneron, Tetrahedron, 1995, 51, 1953 CrossRef CAS.
  9. A. Osuka, S. Nakajima, K. Maruyama, N. Mataga, T. Asahi, I. Yamazaki, Y. Nishimura, T. Ohno and K. Nozaki, J. Am. Chem. Soc., 1993, 115, 4577 CrossRef CAS; G. P. Wiederrecht, M. P. Niemczyk, W. A. Svec and M. R. Wasielewski, J. Am. Chem. Soc., 1996, 118, 81 CrossRef CAS.
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