A cyclic dimer of metalloporphyrin forms a highly stable inclusion complex with C60 [16]

Journal of the American Chemical Society

Volumn 121, Issue 40, 1999, Pages 9477-9478

  Tashiro, Kentaro ^a   Aida, Takuzo ^a   Zheng, Jiang Yu ^a   Kinbara, Kazushi ^a   Saigo, Kazuhiko ^a   Sakamoto, Shigeru ^b   Yamaguchi, Kentaro ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; DIMER; FULLERENE DERIVATIVE; METALLOPORPHYRIN;

CHEMICAL STRUCTURE; COMPLEX FORMATION; LETTER; MOLECULAR MODEL; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0033552239     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992416m     Document Type: Letter

References (20)

1. 60 receptors: (a) Andersson, T.; Nilsson, K.; Sundahl, M.; Westman, G.; Wennerström. J. Chem. Soc., Chem. Commun. 1992, 604. (b) Diederich, F.; Effing, J.; Jonas, U.; Jullien, L.; Plesnivy, T.; Ringsdorf, H.; Thilgen, C.; Weinstein, D. Angew. Chem., Int. Ed. Engl. 1992, 31, 1599. (c) Atwood, J. L.; Koutsantonis, G. A.; Raston, C. L. Nature 1994, 368, 229. (d) Suzuki, T.; Nakashima, K.; Shinkai, S. Chem. Lett. 1994, 699. (e) Yoshida, Z.; Takekuma, H.; Takekuma, S.; Matsubara, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 1597. (f) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 997.
2. 60 receptors: (a) Andersson, T.; Nilsson, K.; Sundahl, M.; Westman, G.; Wennerström. J. Chem. Soc., Chem. Commun. 1992, 604. (b) Diederich, F.; Effing, J.; Jonas, U.; Jullien, L.; Plesnivy, T.; Ringsdorf, H.; Thilgen, C.; Weinstein, D. Angew. Chem., Int. Ed. Engl. 1992, 31, 1599. (c) Atwood, J. L.; Koutsantonis, G. A.; Raston, C. L. Nature 1994, 368, 229. (d) Suzuki, T.; Nakashima, K.; Shinkai, S. Chem. Lett. 1994, 699. (e) Yoshida, Z.; Takekuma, H.; Takekuma, S.; Matsubara, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 1597. (f) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 997.
3. 60 receptors: (a) Andersson, T.; Nilsson, K.; Sundahl, M.; Westman, G.; Wennerström. J. Chem. Soc., Chem. Commun. 1992, 604. (b) Diederich, F.; Effing, J.; Jonas, U.; Jullien, L.; Plesnivy, T.; Ringsdorf, H.; Thilgen, C.; Weinstein, D. Angew. Chem., Int. Ed. Engl. 1992, 31, 1599. (c) Atwood, J. L.; Koutsantonis, G. A.; Raston, C. L. Nature 1994, 368, 229. (d) Suzuki, T.; Nakashima, K.; Shinkai, S. Chem. Lett. 1994, 699. (e) Yoshida, Z.; Takekuma, H.; Takekuma, S.; Matsubara, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 1597. (f) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 997.
4. 60 receptors: (a) Andersson, T.; Nilsson, K.; Sundahl, M.; Westman, G.; Wennerström. J. Chem. Soc., Chem. Commun. 1992, 604. (b) Diederich, F.; Effing, J.; Jonas, U.; Jullien, L.; Plesnivy, T.; Ringsdorf, H.; Thilgen, C.; Weinstein, D. Angew. Chem., Int. Ed. Engl. 1992, 31, 1599. (c) Atwood, J. L.; Koutsantonis, G. A.; Raston, C. L. Nature 1994, 368, 229. (d) Suzuki, T.; Nakashima, K.; Shinkai, S. Chem. Lett. 1994, 699. (e) Yoshida, Z.; Takekuma, H.; Takekuma, S.; Matsubara, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 1597. (f) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 997.
5. 60 receptors: (a) Andersson, T.; Nilsson, K.; Sundahl, M.; Westman, G.; Wennerström. J. Chem. Soc., Chem. Commun. 1992, 604. (b) Diederich, F.; Effing, J.; Jonas, U.; Jullien, L.; Plesnivy, T.; Ringsdorf, H.; Thilgen, C.; Weinstein, D. Angew. Chem., Int. Ed. Engl. 1992, 31, 1599. (c) Atwood, J. L.; Koutsantonis, G. A.; Raston, C. L. Nature 1994, 368, 229. (d) Suzuki, T.; Nakashima, K.; Shinkai, S. Chem. Lett. 1994, 699. (e) Yoshida, Z.; Takekuma, H.; Takekuma, S.; Matsubara, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 1597. (f) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 997.
6. 60 receptors: (a) Andersson, T.; Nilsson, K.; Sundahl, M.; Westman, G.; Wennerström. J. Chem. Soc., Chem. Commun. 1992, 604. (b) Diederich, F.; Effing, J.; Jonas, U.; Jullien, L.; Plesnivy, T.; Ringsdorf, H.; Thilgen, C.; Weinstein, D. Angew. Chem., Int. Ed. Engl. 1992, 31, 1599. (c) Atwood, J. L.; Koutsantonis, G. A.; Raston, C. L. Nature 1994, 368, 229. (d) Suzuki, T.; Nakashima, K.; Shinkai, S. Chem. Lett. 1994, 699. (e) Yoshida, Z.; Takekuma, H.; Takekuma, S.; Matsubara, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 1597. (f) Haino, T.; Yanase, M.; Fukazawa, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 997.
7. 60 systems have been reported to show similar red shifts in the Soret absorption bands. For selected examples, (a) Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771. (b) Kuciauskas, D.; Lin, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D.; Drovetskaya, T.; Reed, C. A.; Boyd, P. D. W. J. Phys. Chem. 1996, 100, 15926. (c) Baran, P. S.; Monaco, R. R.; Khan, A. U.; Schuster, D. I.; Wilson, S. R. J. Am. Chem. Soc. 1997, 119, 8363. (d) Bourgeois, J.-P.; Diederich, F.; Echegoyen, L.; Nierengarten, J.-F. Helv. Chim. Acta 1998, 81, 1835. (e) Dietel, E.; Hirsch, A.; Eichhorn, E.; Rieker, A.; Hackbarth, S.; Röder, B. Chem. Commun. 1998, 1981. (f) Cheng, P.; Wilson, S. R.; Schuster, D. I. Chem. Commun. 1999, 89.
8. 60 systems have been reported to show similar red shifts in the Soret absorption bands. For selected examples, (a) Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771. (b) Kuciauskas, D.; Lin, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D.; Drovetskaya, T.; Reed, C. A.; Boyd, P. D. W. J. Phys. Chem. 1996, 100, 15926. (c) Baran, P. S.; Monaco, R. R.; Khan, A. U.; Schuster, D. I.; Wilson, S. R. J. Am. Chem. Soc. 1997, 119, 8363. (d) Bourgeois, J.-P.; Diederich, F.; Echegoyen, L.; Nierengarten, J.-F. Helv. Chim. Acta 1998, 81, 1835. (e) Dietel, E.; Hirsch, A.; Eichhorn, E.; Rieker, A.; Hackbarth, S.; Röder, B. Chem. Commun. 1998, 1981. (f) Cheng, P.; Wilson, S. R.; Schuster, D. I. Chem. Commun. 1999, 89.
9. 60 systems have been reported to show similar red shifts in the Soret absorption bands. For selected examples, (a) Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771. (b) Kuciauskas, D.; Lin, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D.; Drovetskaya, T.; Reed, C. A.; Boyd, P. D. W. J. Phys. Chem. 1996, 100, 15926. (c) Baran, P. S.; Monaco, R. R.; Khan, A. U.; Schuster, D. I.; Wilson, S. R. J. Am. Chem. Soc. 1997, 119, 8363. (d) Bourgeois, J.-P.; Diederich, F.; Echegoyen, L.; Nierengarten, J.-F. Helv. Chim. Acta 1998, 81, 1835. (e) Dietel, E.; Hirsch, A.; Eichhorn, E.; Rieker, A.; Hackbarth, S.; Röder, B. Chem. Commun. 1998, 1981. (f) Cheng, P.; Wilson, S. R.; Schuster, D. I. Chem. Commun. 1999, 89.
10. 60 systems have been reported to show similar red shifts in the Soret absorption bands. For selected examples, (a) Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771. (b) Kuciauskas, D.; Lin, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D.; Drovetskaya, T.; Reed, C. A.; Boyd, P. D. W. J. Phys. Chem. 1996, 100, 15926. (c) Baran, P. S.; Monaco, R. R.; Khan, A. U.; Schuster, D. I.; Wilson, S. R. J. Am. Chem. Soc. 1997, 119, 8363. (d) Bourgeois, J.-P.; Diederich, F.; Echegoyen, L.; Nierengarten, J.-F. Helv. Chim. Acta 1998, 81, 1835. (e) Dietel, E.; Hirsch, A.; Eichhorn, E.; Rieker, A.; Hackbarth, S.; Röder, B. Chem. Commun. 1998, 1981. (f) Cheng, P.; Wilson, S. R.; Schuster, D. I. Chem. Commun. 1999, 89.
11. 60 systems have been reported to show similar red shifts in the Soret absorption bands. For selected examples, (a) Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771. (b) Kuciauskas, D.; Lin, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D.; Drovetskaya, T.; Reed, C. A.; Boyd, P. D. W. J. Phys. Chem. 1996, 100, 15926. (c) Baran, P. S.; Monaco, R. R.; Khan, A. U.; Schuster, D. I.; Wilson, S. R. J. Am. Chem. Soc. 1997, 119, 8363. (d) Bourgeois, J.-P.; Diederich, F.; Echegoyen, L.; Nierengarten, J.-F. Helv. Chim. Acta 1998, 81, 1835. (e) Dietel, E.; Hirsch, A.; Eichhorn, E.; Rieker, A.; Hackbarth, S.; Röder, B. Chem. Commun. 1998, 1981. (f) Cheng, P.; Wilson, S. R.; Schuster, D. I. Chem. Commun. 1999, 89.
12. 60 systems have been reported to show similar red shifts in the Soret absorption bands. For selected examples, (a) Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771. (b) Kuciauskas, D.; Lin, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D.; Drovetskaya, T.; Reed, C. A.; Boyd, P. D. W. J. Phys. Chem. 1996, 100, 15926. (c) Baran, P. S.; Monaco, R. R.; Khan, A. U.; Schuster, D. I.; Wilson, S. R. J. Am. Chem. Soc. 1997, 119, 8363. (d) Bourgeois, J.-P.; Diederich, F.; Echegoyen, L.; Nierengarten, J.-F. Helv. Chim. Acta 1998, 81, 1835. (e) Dietel, E.; Hirsch, A.; Eichhorn, E.; Rieker, A.; Hackbarth, S.; Röder, B. Chem. Commun. 1998, 1981. (f) Cheng, P.; Wilson, S. R.; Schuster, D. I. Chem. Commun. 1999, 89.
13. -1.
14. 2 = 0.999417).
15. 1H NMR spectra, see Supporting Information. Presence of conformational isomers in analogous dimeric porphyrin systems has been reported in Golubchikov, O. A.; Mamardashvili, N. Zh.; Semeikin, A. S. Zh. Org. Khim. 1993, 29, 2445.
16. Sanders, J. K. M.; Hunter, B. K. Modern NMR Spectroscopy; Oxford University: Oxford, U.K., 1987.
17. -1, as determined spectroscopically.
18. Bampos, N.; Marvaud, V.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 335.
19. +.
20. A comparable cathodic shift of the reduction potential has been reported in ref 2d.