Nonameric porphyrin assemblies - Formation and intra-assembly energy transfer reactions

Organic and Biomolecular Chemistry

Volumn 2, Issue 19, 2004, Pages 2852-2860

  Sasaki, Ken ^a   Sugou, Kenji ^a   Miyamoto, Koji ^a   Hirai, Jyun Ichi ^a   Tsubouchi, Shigetaka ^a   Miyasaka, Hiroshi ^b   Itaya, Akira ^a   Kuroda, Yasuhisa ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CARBOXYLIC ACIDS; ENERGY TRANSFER; FLUORESCENCE; LIGHT PROPAGATION; METHANOL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOSYNTHESIS; SOLVENTS;

ALKYL CHAINS; CHEMICAL FUNCTIONS; LIGHT-COLLECTION EFFECTS; PHOTOSYNTHETIC LIGHT-HARVESTING SYSTEMS;

PORPHYRINS;

PORPHYRIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ENERGY TRANSFER; KINETICS; SPECTROSCOPY; SYNTHESIS;

ENERGY TRANSFER; KINETICS; MOLECULAR STRUCTURE; PORPHYRINS; SPECTRUM ANALYSIS;

EID: 6344219560     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b408023h     Document Type: Article

References (46)

1. J. Deisenhofer, O. Epp, K. Miki, R. Huber and H. Michel, Nature, 1985, 318, 618; G. McDermott, S. M. Prince, A. A. Freer, A. M. Hawthornthwaite- Lawless, M. Z. Papiz, R. J. Cogdell and N. W. Isaacs, Nature, 1995, 374, 517; T. Pullerits and V. Sundstrom, Acc. Chem. Res., 1996, 29, 381.
2. J. Deisenhofer, O. Epp, K. Miki, R. Huber and H. Michel, Nature, 1985, 318, 618; G. McDermott, S. M. Prince, A. A. Freer, A. M. Hawthornthwaite- Lawless, M. Z. Papiz, R. J. Cogdell and N. W. Isaacs, Nature, 1995, 374, 517; T. Pullerits and V. Sundstrom, Acc. Chem. Res., 1996, 29, 381.
3. J. Deisenhofer, O. Epp, K. Miki, R. Huber and H. Michel, Nature, 1985, 318, 618; G. McDermott, S. M. Prince, A. A. Freer, A. M. Hawthornthwaite- Lawless, M. Z. Papiz, R. J. Cogdell and N. W. Isaacs, Nature, 1995, 374, 517; T. Pullerits and V. Sundstrom, Acc. Chem. Res., 1996, 29, 381.
4. For examples of recent developments, see: M. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; H. Kurreck and M. Fuber, Angew. Chem., Int. Ed. Engl., 1995, 34, 849; A. Harriman and J.-P. Sauvage, Chem. Soc. Rev., 1996, 24, 41; V. Balzani, A. Juris, M. Venturi, S. Champagna and S. Serroni, Chem. Rev., 1996, 96, 759; M.-J. Blanco, M. C. Jiménez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 2001, 34, 40; M.d. R. Benitetes, T. E. Johnson, S. Weghorn, L. Yu, P. D. Rao, J. R. Diers, S. I. Yang, C. Kimaier, D. F. Bocian, D. Holte and J. S. Lindsey, J. Mater. Chem., 2002, 12, 65; V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines - A Journey into the Nono World, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2003.
5. For examples of recent developments, see: M. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; H. Kurreck and M. Fuber, Angew. Chem., Int. Ed. Engl., 1995, 34, 849; A. Harriman and J.-P. Sauvage, Chem. Soc. Rev., 1996, 24, 41; V. Balzani, A. Juris, M. Venturi, S. Champagna and S. Serroni, Chem. Rev., 1996, 96, 759; M.-J. Blanco, M. C. Jiménez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 2001, 34, 40; M.d. R. Benitetes, T. E. Johnson, S. Weghorn, L. Yu, P. D. Rao, J. R. Diers, S. I. Yang, C. Kimaier, D. F. Bocian, D. Holte and J. S. Lindsey, J. Mater. Chem., 2002, 12, 65; V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines - A Journey into the Nono World, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2003.
6. For examples of recent developments, see: M. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; H. Kurreck and M. Fuber, Angew. Chem., Int. Ed. Engl., 1995, 34, 849; A. Harriman and J.-P. Sauvage, Chem. Soc. Rev., 1996, 24, 41; V. Balzani, A. Juris, M. Venturi, S. Champagna and S. Serroni, Chem. Rev., 1996, 96, 759; M.-J. Blanco, M. C. Jiménez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 2001, 34, 40; M.d. R. Benitetes, T. E. Johnson, S. Weghorn, L. Yu, P. D. Rao, J. R. Diers, S. I. Yang, C. Kimaier, D. F. Bocian, D. Holte and J. S. Lindsey, J. Mater. Chem., 2002, 12, 65; V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines - A Journey into the Nono World, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2003.
7. For examples of recent developments, see: M. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; H. Kurreck and M. Fuber, Angew. Chem., Int. Ed. Engl., 1995, 34, 849; A. Harriman and J.-P. Sauvage, Chem. Soc. Rev., 1996, 24, 41; V. Balzani, A. Juris, M. Venturi, S. Champagna and S. Serroni, Chem. Rev., 1996, 96, 759; M.-J. Blanco, M. C. Jiménez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 2001, 34, 40; M.d. R. Benitetes, T. E. Johnson, S. Weghorn, L. Yu, P. D. Rao, J. R. Diers, S. I. Yang, C. Kimaier, D. F. Bocian, D. Holte and J. S. Lindsey, J. Mater. Chem., 2002, 12, 65; V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines - A Journey into the Nono World, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2003.
8. For examples of recent developments, see: M. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; H. Kurreck and M. Fuber, Angew. Chem., Int. Ed. Engl., 1995, 34, 849; A. Harriman and J.-P. Sauvage, Chem. Soc. Rev., 1996, 24, 41; V. Balzani, A. Juris, M. Venturi, S. Champagna and S. Serroni, Chem. Rev., 1996, 96, 759; M.-J. Blanco, M. C. Jiménez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 2001, 34, 40; M.d. R. Benitetes, T. E. Johnson, S. Weghorn, L. Yu, P. D. Rao, J. R. Diers, S. I. Yang, C. Kimaier, D. F. Bocian, D. Holte and J. S. Lindsey, J. Mater. Chem., 2002, 12, 65; V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines - A Journey into the Nono World, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2003.
9. For examples of recent developments, see: M. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; H. Kurreck and M. Fuber, Angew. Chem., Int. Ed. Engl., 1995, 34, 849; A. Harriman and J.-P. Sauvage, Chem. Soc. Rev., 1996, 24, 41; V. Balzani, A. Juris, M. Venturi, S. Champagna and S. Serroni, Chem. Rev., 1996, 96, 759; M.-J. Blanco, M. C. Jiménez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 2001, 34, 40; M.d. R. Benitetes, T. E. Johnson, S. Weghorn, L. Yu, P. D. Rao, J. R. Diers, S. I. Yang, C. Kimaier, D. F. Bocian, D. Holte and J. S. Lindsey, J. Mater. Chem., 2002, 12, 65; V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines - A Journey into the Nono World, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2003.
10. For examples of recent developments, see: M. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; H. Kurreck and M. Fuber, Angew. Chem., Int. Ed. Engl., 1995, 34, 849; A. Harriman and J.-P. Sauvage, Chem. Soc. Rev., 1996, 24, 41; V. Balzani, A. Juris, M. Venturi, S. Champagna and S. Serroni, Chem. Rev., 1996, 96, 759; M.-J. Blanco, M. C. Jiménez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 2001, 34, 40; M.d. R. Benitetes, T. E. Johnson, S. Weghorn, L. Yu, P. D. Rao, J. R. Diers, S. I. Yang, C. Kimaier, D. F. Bocian, D. Holte and J. S. Lindsey, J. Mater. Chem., 2002, 12, 65; V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines - A Journey into the Nono World, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2003.
11. For examples of recent developments, see: M. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; H. Kurreck and M. Fuber, Angew. Chem., Int. Ed. Engl., 1995, 34, 849; A. Harriman and J.-P. Sauvage, Chem. Soc. Rev., 1996, 24, 41; V. Balzani, A. Juris, M. Venturi, S. Champagna and S. Serroni, Chem. Rev., 1996, 96, 759; M.-J. Blanco, M. C. Jiménez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 2001, 34, 40; M.d. R. Benitetes, T. E. Johnson, S. Weghorn, L. Yu, P. D. Rao, J. R. Diers, S. I. Yang, C. Kimaier, D. F. Bocian, D. Holte and J. S. Lindsey, J. Mater. Chem., 2002, 12, 65; V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines - A Journey into the Nono World, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2003.
12. For examples of recent developments, see: M. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; H. Kurreck and M. Fuber, Angew. Chem., Int. Ed. Engl., 1995, 34, 849; A. Harriman and J.-P. Sauvage, Chem. Soc. Rev., 1996, 24, 41; V. Balzani, A. Juris, M. Venturi, S. Champagna and S. Serroni, Chem. Rev., 1996, 96, 759; M.-J. Blanco, M. C. Jiménez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 2001, 34, 40; M.d. R. Benitetes, T. E. Johnson, S. Weghorn, L. Yu, P. D. Rao, J. R. Diers, S. I. Yang, C. Kimaier, D. F. Bocian, D. Holte and J. S. Lindsey, J. Mater. Chem., 2002, 12, 65; V. Balzani, A. Credi, M. Venturi, Molecular Devices and Machines - A Journey into the Nono World, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2003.
13. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
14. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
15. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
16. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
17. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
18. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
19. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
20. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
21. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
22. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
23. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
24. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
25. For recent reviews of the porphyrin assemblies, see: H. Ogoshi, T. Mizutani, T. Hayashi and Y. Kuroda, in The Porphyrin Handbook. Vol.6, Applications: Past, Present and Future, K. M. Kadish, K. M. Smith and R. Guilard, ed., Academic Press, New York, 2000, pp. 279-340; and A. K. Burell, D. L. Officer, P. G. Plieger and D. C. W. Reid, Chem. Rev., 2001, 101, 2751. For examples of trimeric or lager porphyrin assemblies, see: P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi, D. H. Waldeck and A. D. Hamilton, J. Am. Chem. Soc., 1990, 112, 9408; A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632; F. Odobel and J.-P. Sauvage, New J. Chem., 1994, 18, 1139; S. Anderson, H. L. Anderson, A. Bashall, M. Mcpartlin and J. K. M. Sanders, Angew.Chem., Int. Ed. Engl., 1995, 34, 1096; A. V. Chernook, U. Rempel, C. von Borczyskowski, A. M. Shulgam and E. I. Zenkevich, Chem. Phys. Lett., 1996, 254, 229; C. A. Hunter and R. K. Hyde, Angew.Chem., Int. Ed. Engl., 1996, 35, 1936; C. M. Drain, K. C. Russell and J.-M. Lehn, Chem. Commun., 1996, 337; Y. Kuroda, Y. Kato and H. Ogoshi, Chem. Commun., 1997, 469; Y. Kuroda, N. Shiraishi, K. Sugou, K. Sasaki and H. Ogoshi, Tetrahedron Lett., 1998, 39, 2993; P. N. Taylor and H. L. Anderson, J. Am. Chem Soc., 1999, 121, 11538; R. Takahashi and Y. Kobuke, J. Am. Chem. Soc., 2003, 125, 2372.
26. Y. Kuroda, K. Sugou and K. Sasaki, J. Am. Chem. Soc., 2000, 122, 7833; K. Sugou, K. Sasaki, K. Kitajima, T. Iwaki and Y. Kuroda, J. Am. Chem. Soc., 2002, 124, 1182.
27. Y. Kuroda, K. Sugou and K. Sasaki, J. Am. Chem. Soc., 2000, 122, 7833; K. Sugou, K. Sasaki, K. Kitajima, T. Iwaki and Y. Kuroda, J. Am. Chem. Soc., 2002, 124, 1182.
28. Y. Kuroda, A. Kawashima, T. Urai and H. Ogoshi, Tetrahedron Lett., 1995, 36, 8449; Y. Kuroda, A. Kawashima and H. Ogoshi, Chem. Lett., 1996, 57; Y. Kuroda, A. Kawashima, Y. Hayashi and H. Ogoshi, J. Am. Chem. Soc., 1997, 119, 4929.
29. Y. Kuroda, A. Kawashima, T. Urai and H. Ogoshi, Tetrahedron Lett., 1995, 36, 8449; Y. Kuroda, A. Kawashima and H. Ogoshi, Chem. Lett., 1996, 57; Y. Kuroda, A. Kawashima, Y. Hayashi and H. Ogoshi, J. Am. Chem. Soc., 1997, 119, 4929.
30. Y. Kuroda, A. Kawashima, T. Urai and H. Ogoshi, Tetrahedron Lett., 1995, 36, 8449; Y. Kuroda, A. Kawashima and H. Ogoshi, Chem. Lett., 1996, 57; Y. Kuroda, A. Kawashima, Y. Hayashi and H. Ogoshi, J. Am. Chem. Soc., 1997, 119, 4929.
31. Y. Houminer, R. A. Fenner, H. V. Secor and J. I. Seemann, J. Org. Chem., 1987, 52, 3971.
32. The analyses and manipulation of the electronic and the fluorescence spectra in this work were performed by using the software SPANA developed in this laboratory, which is available from our web-site, http://www.poly.kit.ac. jp/~kinosekk/index.html.
33. 4 assemblies tend to broaden compared with those composed of the corresponding component spectra. For the spectroscopic effect of the multi-porphyrin interaction, see, for example: T. Nagata, A. Osuka and K. Maruyama, J. Am. Chem. Soc., 1990, 112, 3054; A. Osuka, N. Tanabe, S. Nakajima and K. Maruyama, J. Chem. Soc., Perkin Trans. 2, 1996, 199.
34. 4 assemblies tend to broaden compared with those composed of the corresponding component spectra. For the spectroscopic effect of the multi-porphyrin interaction, see, for example: T. Nagata, A. Osuka and K. Maruyama, J. Am. Chem. Soc., 1990, 112, 3054; A. Osuka, N. Tanabe, S. Nakajima and K. Maruyama, J. Chem. Soc., Perkin Trans. 2, 1996, 199.
35. For the theoretical treatment of the multiple equilibrium processes, see: C. Tanford, Physical Chemistry of Macromolecules, John Wiley & Sons, New York, 1961.
36. Since the larger value of the binding constant gives practically the same theoretical curve fitting, the value determined by the present titration is regarded as a minimum estimate.
37. J. A. Blackburn, Anal. Chem., 1965, 37, 1000.
38. T. Förster, Fluorenzenz Organische Verbindungen, Vandenhoech and Ruprech, Göttingen, 1951; T. Förster, Ann. Physik, 1948, 2, 55; T. Förster, Discuss. Faraday Soc., 1959, 27, 7. For an example of practical application for the energy transfer between porphyrins, see: J. L. Sessler, B. Wang and A. Harriman, J. Am. Chem. Soc., 1995, 117, 704.
39. T. Förster, Fluorenzenz Organische Verbindungen, Vandenhoech and Ruprech, Göttingen, 1951; T. Förster, Ann. Physik, 1948, 2, 55; T. Förster, Discuss. Faraday Soc., 1959, 27, 7. For an example of practical application for the energy transfer between porphyrins, see: J. L. Sessler, B. Wang and A. Harriman, J. Am. Chem. Soc., 1995, 117, 704.
40. T. Förster, Fluorenzenz Organische Verbindungen, Vandenhoech and Ruprech, Göttingen, 1951; T. Förster, Ann. Physik, 1948, 2, 55; T. Förster, Discuss. Faraday Soc., 1959, 27, 7. For an example of practical application for the energy transfer between porphyrins, see: J. L. Sessler, B. Wang and A. Harriman, J. Am. Chem. Soc., 1995, 117, 704.
41. T. Förster, Fluorenzenz Organische Verbindungen, Vandenhoech and Ruprech, Göttingen, 1951; T. Förster, Ann. Physik, 1948, 2, 55; T. Förster, Discuss. Faraday Soc., 1959, 27, 7. For an example of practical application for the energy transfer between porphyrins, see: J. L. Sessler, B. Wang and A. Harriman, J. Am. Chem. Soc., 1995, 117, 704.
42. # is expected to be minor; (b) a variation of the orientation factor of medium values results in minor error in the estimation of the distance because of the sixth root relationship, see, for example: B. Valeur, Molecular Fluorescence, Wiley-VCH Verlag GmbH, Weinheim, 2002.
43. P. J. Flory, Statistical Mechanics of Chain Molecules, John Wiley & Sons, Inc., New York, 1969.
44. 5 assembly may be explained by the contribution of the Dexter mechanism as shown by the dashed line in Fig. 9. This attractive possibility is important for the further detailed investigation of assemblies which have the donor-acceptor distance in the transitional region for the Dexter and Förster mechanisms. See, for related discussions: P. Brodard, S. Matzinger, E. Vauthey, O. Mongin, C. Papamicael and A. Gossauer, J. Phys. Chem. A, 1999, 103, 5858; S. Faure, C. Stern, R. Guilard and P. D. Harvey, J. Am. Chem. Soc., 2004, 126, 1253.
45. 5 assembly may be explained by the contribution of the Dexter mechanism as shown by the dashed line in Fig. 9. This attractive possibility is important for the further detailed investigation of assemblies which have the donor-acceptor distance in the transitional region for the Dexter and Förster mechanisms. See, for related discussions: P. Brodard, S. Matzinger, E. Vauthey, O. Mongin, C. Papamicael and A. Gossauer, J. Phys. Chem. A, 1999, 103, 5858; S. Faure, C. Stern, R. Guilard and P. D. Harvey, J. Am. Chem. Soc., 2004, 126, 1253.
46. M.-S. Choi, T. Aida, T. Yamazaki and I. Yamazaki, Chem. Eur. J, 2002, 8, 2667.