Nonameric porphyrin assembly: Antenna effect on energy transfer [12]

Journal of the American Chemical Society

Volumn 122, Issue 32, 2000, Pages 7833-7834

  Kuroda, Yasuhisa ^a   Sugou, Kenji ^a   Sasaki, Ken ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN;

COMPLEX FORMATION; ENERGY TRANSFER; LETTER; MOLECULAR INTERACTION; PHOTOSYNTHESIS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0034674927     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001506k     Document Type: Letter

References (23)

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4. For recent review, see: Ogoshi, H.; Mizutani, T.; Hayashi, T.; Kuroda, Y. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Applications: Past, Present and Future, Vol. 6; Academic Press: New York, 2000; pp 279-340.
5. For examples of trimeric or larger porphyrin assemblies, see: (a) Tecilla, P.; Dixon, R. P.; Slobodkin, G.; Alavi, D. S.; Waldeck, D. H.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 9408. (b) Brun, A. M.; Atherton, S. J.; Harriman, A.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1992, 114, 4632. Odobel, F.; Sauvage, J.-P. New J. Chem. 1994, 18, 1139. Anderson, S.; Anderson, H. L.; Bashall, A.; Mcpartlin, M.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1096. (e) Chernook, A. V.; Rempel, U.; von Borczyskowski, C.; Shulgam, A. M.; Zenkevich, E. I. Chem. Phys. Lett. 1996, 254, 229. (f) Hunter, C. A.; Hyde, R. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1936. (g) Drain, C. M.; Russell, K. C.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1996, 337. (h) Kuroda, Y.; Kato, Y.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1997, 469. Kuroda, Y.; Shiraishi, N.; Sugou, K.; Sasaki, K.; Ogoshi, H. Tetrahedron Lett. 1998, 39, 2993.
6. For examples of trimeric or larger porphyrin assemblies, see: (a) Tecilla, P.; Dixon, R. P.; Slobodkin, G.; Alavi, D. S.; Waldeck, D. H.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 9408. (b) Brun, A. M.; Atherton, S. J.; Harriman, A.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1992, 114, 4632. Odobel, F.; Sauvage, J.-P. New J. Chem. 1994, 18, 1139. Anderson, S.; Anderson, H. L.; Bashall, A.; Mcpartlin, M.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1096. (e) Chernook, A. V.; Rempel, U.; von Borczyskowski, C.; Shulgam, A. M.; Zenkevich, E. I. Chem. Phys. Lett. 1996, 254, 229. (f) Hunter, C. A.; Hyde, R. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1936. (g) Drain, C. M.; Russell, K. C.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1996, 337. (h) Kuroda, Y.; Kato, Y.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1997, 469. Kuroda, Y.; Shiraishi, N.; Sugou, K.; Sasaki, K.; Ogoshi, H. Tetrahedron Lett. 1998, 39, 2993.
7. For examples of trimeric or larger porphyrin assemblies, see: (a) Tecilla, P.; Dixon, R. P.; Slobodkin, G.; Alavi, D. S.; Waldeck, D. H.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 9408. (b) Brun, A. M.; Atherton, S. J.; Harriman, A.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1992, 114, 4632. Odobel, F.; Sauvage, J.-P. New J. Chem. 1994, 18, 1139. Anderson, S.; Anderson, H. L.; Bashall, A.; Mcpartlin, M.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1096. (e) Chernook, A. V.; Rempel, U.; von Borczyskowski, C.; Shulgam, A. M.; Zenkevich, E. I. Chem. Phys. Lett. 1996, 254, 229. (f) Hunter, C. A.; Hyde, R. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1936. (g) Drain, C. M.; Russell, K. C.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1996, 337. (h) Kuroda, Y.; Kato, Y.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1997, 469. Kuroda, Y.; Shiraishi, N.; Sugou, K.; Sasaki, K.; Ogoshi, H. Tetrahedron Lett. 1998, 39, 2993.
8. For examples of trimeric or larger porphyrin assemblies, see: (a) Tecilla, P.; Dixon, R. P.; Slobodkin, G.; Alavi, D. S.; Waldeck, D. H.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 9408. (b) Brun, A. M.; Atherton, S. J.; Harriman, A.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1992, 114, 4632. Odobel, F.; Sauvage, J.-P. New J. Chem. 1994, 18, 1139. Anderson, S.; Anderson, H. L.; Bashall, A.; Mcpartlin, M.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1096. (e) Chernook, A. V.; Rempel, U.; von Borczyskowski, C.; Shulgam, A. M.; Zenkevich, E. I. Chem. Phys. Lett. 1996, 254, 229. (f) Hunter, C. A.; Hyde, R. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1936. (g) Drain, C. M.; Russell, K. C.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1996, 337. (h) Kuroda, Y.; Kato, Y.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1997, 469. Kuroda, Y.; Shiraishi, N.; Sugou, K.; Sasaki, K.; Ogoshi, H. Tetrahedron Lett. 1998, 39, 2993.
9. For examples of trimeric or larger porphyrin assemblies, see: (a) Tecilla, P.; Dixon, R. P.; Slobodkin, G.; Alavi, D. S.; Waldeck, D. H.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 9408. (b) Brun, A. M.; Atherton, S. J.; Harriman, A.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1992, 114, 4632. Odobel, F.; Sauvage, J.-P. New J. Chem. 1994, 18, 1139. Anderson, S.; Anderson, H. L.; Bashall, A.; Mcpartlin, M.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1096. (e) Chernook, A. V.; Rempel, U.; von Borczyskowski, C.; Shulgam, A. M.; Zenkevich, E. I. Chem. Phys. Lett. 1996, 254, 229. (f) Hunter, C. A.; Hyde, R. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1936. (g) Drain, C. M.; Russell, K. C.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1996, 337. (h) Kuroda, Y.; Kato, Y.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1997, 469. Kuroda, Y.; Shiraishi, N.; Sugou, K.; Sasaki, K.; Ogoshi, H. Tetrahedron Lett. 1998, 39, 2993.
10. For examples of trimeric or larger porphyrin assemblies, see: (a) Tecilla, P.; Dixon, R. P.; Slobodkin, G.; Alavi, D. S.; Waldeck, D. H.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 9408. (b) Brun, A. M.; Atherton, S. J.; Harriman, A.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1992, 114, 4632. Odobel, F.; Sauvage, J.-P. New J. Chem. 1994, 18, 1139. Anderson, S.; Anderson, H. L.; Bashall, A.; Mcpartlin, M.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1096. (e) Chernook, A. V.; Rempel, U.; von Borczyskowski, C.; Shulgam, A. M.; Zenkevich, E. I. Chem. Phys. Lett. 1996, 254, 229. (f) Hunter, C. A.; Hyde, R. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1936. (g) Drain, C. M.; Russell, K. C.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1996, 337. (h) Kuroda, Y.; Kato, Y.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1997, 469. Kuroda, Y.; Shiraishi, N.; Sugou, K.; Sasaki, K.; Ogoshi, H. Tetrahedron Lett. 1998, 39, 2993.
11. For examples of trimeric or larger porphyrin assemblies, see: (a) Tecilla, P.; Dixon, R. P.; Slobodkin, G.; Alavi, D. S.; Waldeck, D. H.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 9408. (b) Brun, A. M.; Atherton, S. J.; Harriman, A.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1992, 114, 4632. Odobel, F.; Sauvage, J.-P. New J. Chem. 1994, 18, 1139. Anderson, S.; Anderson, H. L.; Bashall, A.; Mcpartlin, M.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1096. (e) Chernook, A. V.; Rempel, U.; von Borczyskowski, C.; Shulgam, A. M.; Zenkevich, E. I. Chem. Phys. Lett. 1996, 254, 229. (f) Hunter, C. A.; Hyde, R. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1936. (g) Drain, C. M.; Russell, K. C.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1996, 337. (h) Kuroda, Y.; Kato, Y.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1997, 469. Kuroda, Y.; Shiraishi, N.; Sugou, K.; Sasaki, K.; Ogoshi, H. Tetrahedron Lett. 1998, 39, 2993.
12. For examples of trimeric or larger porphyrin assemblies, see: (a) Tecilla, P.; Dixon, R. P.; Slobodkin, G.; Alavi, D. S.; Waldeck, D. H.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 9408. (b) Brun, A. M.; Atherton, S. J.; Harriman, A.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1992, 114, 4632. Odobel, F.; Sauvage, J.-P. New J. Chem. 1994, 18, 1139. Anderson, S.; Anderson, H. L.; Bashall, A.; Mcpartlin, M.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1096. (e) Chernook, A. V.; Rempel, U.; von Borczyskowski, C.; Shulgam, A. M.; Zenkevich, E. I. Chem. Phys. Lett. 1996, 254, 229. (f) Hunter, C. A.; Hyde, R. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1936. (g) Drain, C. M.; Russell, K. C.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1996, 337. (h) Kuroda, Y.; Kato, Y.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1997, 469. Kuroda, Y.; Shiraishi, N.; Sugou, K.; Sasaki, K.; Ogoshi, H. Tetrahedron Lett. 1998, 39, 2993.
13. For examples of trimeric or larger porphyrin assemblies, see: (a) Tecilla, P.; Dixon, R. P.; Slobodkin, G.; Alavi, D. S.; Waldeck, D. H.; Hamilton, A. D. J. Am. Chem. Soc. 1990, 112, 9408. (b) Brun, A. M.; Atherton, S. J.; Harriman, A.; Heitz, V.; Sauvage, J.-P. J. Am. Chem. Soc. 1992, 114, 4632. Odobel, F.; Sauvage, J.-P. New J. Chem. 1994, 18, 1139. Anderson, S.; Anderson, H. L.; Bashall, A.; Mcpartlin, M.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1096. (e) Chernook, A. V.; Rempel, U.; von Borczyskowski, C.; Shulgam, A. M.; Zenkevich, E. I. Chem. Phys. Lett. 1996, 254, 229. (f) Hunter, C. A.; Hyde, R. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 1936. (g) Drain, C. M.; Russell, K. C.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1996, 337. (h) Kuroda, Y.; Kato, Y.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1997, 469. Kuroda, Y.; Shiraishi, N.; Sugou, K.; Sasaki, K.; Ogoshi, H. Tetrahedron Lett. 1998, 39, 2993.
14. (a) Kuroda, Y.; Kawashima, A.; Urai, T.; Ogoshi, H. Tetrahedron Lett. 1995, 36, 8449.
15. (b) Kuroda, Y.; Kawashima, A.; Ogoshi, H. Chem. Lett. 1996, 57.
16. Kuroda, Y.; Kawashima, A.; Hayashi, Y.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 4929.
17. For the theoretical treatment of the multiple equiribrium processes, see Tanford, C. Physical Chemistry of Macromolecules; John Wiley & Sons: New York, 1961.
18. -6 M) are estimated to be ∼70, 25, 4, and < 1%, respectively.
19. The data of Job plot analysis of the present system show maximum assembly formation at ∼0.8 of the molar fraction of 2 which is consistent with the nonameric assembly.
20. The relative quantum yield is determined by the reported method, see: Hsiao, J.-S.; Krueger, B. K.; Wagner, R. W.; Johnson, T. E.; Delaney, J. K.; Mauzerall, D. C.; Fleming, G. R.; Lindsey, J. E.; Bocian, D. F.; Donohoe, R. J. J. Am. Chem. Soc. 1996, 118, 11181.
21. The contribution of the fluorescence of uncomplexed 2 to the resulting emmission is estimated to be less than 1%. For present estimation of the energy transfer efficiency, multiply excited assemblies containing two or more excited porphyrins are not taken into consideration.
22. The energy transfer is less efficient than that observed for covalently linked multi-porphyrin systems (>0.9) where the through-bond mechanism of energy transfer is proposed, see, for example: Wagner, R. W.; Lindsey, J. S. J. Am. Chem. Soc. 1994, 116, 9759, but more efficient than that for assemblies linked with hydrogen bonds (∼0.6) where the through-space mechanism is proposed, see: Sessler, J. L.; Wang, B.; Harriman, A. J. Am. Chem. Soc. 1995, 117, 704. The preliminary estimation, assuming Förster mechanism and using spectroscopic data and typical known lifetime data, indicates that the observed efficiency corresponds to 17-18 Å center-to-center separation between the donor-acceptor porphyrins.
23. The energy transfer is less efficient than that observed for covalently linked multi-porphyrin systems (>0.9) where the through-bond mechanism of energy transfer is proposed, see, for example: Wagner, R. W.; Lindsey, J. S. J. Am. Chem. Soc. 1994, 116, 9759, but more efficient than that for assemblies linked with hydrogen bonds (∼0.6) where the through-space mechanism is proposed, see: Sessler, J. L.; Wang, B.; Harriman, A. J. Am. Chem. Soc. 1995, 117, 704. The preliminary estimation, assuming Förster mechanism and using spectroscopic data and typical known lifetime data, indicates that the observed efficiency corresponds to 17-18 Å center-to-center separation between the donor-acceptor porphyrins.