Synthesis of unsymmetrical porphyrin dimers containing β-octaalkyl and meso-tetraphenylporphyrin subunits

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2637-2640

  Paolesse, Roberto ^a   Tagliatesta, Pietro ^a   Boschi, Tristano ^a  

^a UNIVERSITY OF ROME TOR VERGATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029915318     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00348-6     Document Type: Article

References (30)

1. (a) Deisenhofer, J.; Epp, O.; Miki, K.; Huber, R.; Michel, H. J. Mol. Biol., 1984, 180, 385.
2. (b) Allen, J. P.; Feher, G.; Yeates, T. O.; Rees, D. C.; Deisenhofer, J.; Michel, H.; Huber, R. Proc. Natl. Acad. Sci. USA, 1986, 83, 8589.
3. (c) Allen, J. P.; Feher, G. Proc. Natl. Acad. Sci., USA, 1984, 81, 4795.
4. (a) Kurreck H.; Huber M. Angew. Chem. Int. Ed. Engl. 1995, 34, 849 and references therein .
5. (b) Chang, C. K.; Abdalmuhdi, I. J. Org. Chem., 1983, 48, 5388.
6. (c) Chang, C. K.; Abdalmuhdi, I. Angew. Chem., Int. Edn. Engl., 1984, 23, 164.
7. (d) Sessler, J. L.; Johnson, M. R.; Lin, T. Y.; Creager, S. E. J. Am. Chem. Soc., 1988, 110, 3659.
8. (e) Sessler, J. L.; Hugdahl, J.; Johnson, M. R. J. Org. Chem., 1986, 51, 2838.
9. (f) Chang, C. K.; Abdalmuhdi, I. J. Org. Chem., 1985, 50, 411.
10. (a) Gust, D.; Moore, T. A.; Moore A. L.; Makings, L. R.; Seely, G. R.; Ma, X.; Trier, T. T.; Gao, F. J. Am. Chem. Soc., 1988, 110, 3659.
11. (b) Moore, T. A.; Gust, D.; Mathis, P.; Mialocq, J. C.; Chachaty, C.; Bensasson, R. V.; Land, E. J.; Doizi, D.; Liddell, P. A.; Lehman, W. R.; Nemeth, G. A.; Moore, A. L. Nature (London) 1984, 307, 630.
12. (c) Osuka, A.; Hiroko, Y; Maruyama, K. Chem Lett., 1990, 1905.
13. (d) Osuka, A.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1988, 1243.
14. (e) Osuka, A.; Maruyama, K.; Mataga, N.; Asahi, T.; Yamazaki, I.; Tamai, N. J. Am. Chem. Soc. 1990, 112, 4958.
15. (f) Helms, A.; Heiler, D.; Mc Lendon, G. J. Am. Chem. Soc. 1992, 114, 6227.
16. (a) Park, G.I.; Nakajima, S.; Osuka, A.; Kim, K. Chem. Lett. 1995, 255.
17. (b) Naruta, Y.; Sasayama M.; Sasaki, T. Angew. Chem. Int. Ed. Engl. 1994, 33, 1839.
18. (a) Kessel, D.; Dougherty, T.J.; Chang, C.K. Photochem Photobiol., 1991, 53, 475.
19. (b) Pandey, R.K.; Shiau, F.Y.; Medforth, C.J.; Dougherty, T.J.; Smith, K.M. Tetrahedron Lett., 1990, 31, 789.
20. (a) Wasielewski, M. R.; Johnson, D. G.; Niemczyk, M. P.; Gaines, G. L.; O'Neil, M. P.; Svec, V. A. J. Am. Chem. Soc. 1990, 112, 6482.
21. (b) Gust, D.; Moore, T. A.; Moore, A. L.; Krasnovsky, Jr., A. A.; Liddell, P. A.; Nicodem, D.; DeGraziano, J. M.; Kerrigan, P.; Makings, L. R.; Pessiki, P. J. J. Am. Chem. Soc., 1993, 115, 5684.
22. (c) Osuka, A; Marumo, S.; Maruyama, K.; Mataga N. Bull. Chem. Soc. Jpn. 1995 68, 262.
23. Setsune, J.; Yoshida, Z.; Ogoshi, H. J. Chem. Soc., Perkin Trans. I, 1982, 983.
24. Maruyama, K.; Nagata, T.; Ono, N.; Osuka, A. Bull. Chem. Soc. Jpn., 1989, 62, 3167.
25. Kim, J.B.; Adler, A.D.; Longo, F.R. in The Porphyrins, Dolphin, D. ed., Academic Press: New York, 1978, p. 85.
26. Buchler, J.W. in The Porphyrins, Dolphin, D. ed., Academic Press: New York, 1978, p. 389 and references therein.
27. Fuhrop, J.H. and Smith, K.M. in Porphyrins and Metalloporphyrins, Smith, K.M. ed., Elsevier: Amsterdam, 1975, p. 757.
28. 3): 10.24 (s, 2H), 10.01 (s, 1H), 9.31, 9.12 (each d, 4H), 8.95 (m, 4H), 8.57, 8.39 (each d, 4H), 8.32-8.26 (m, 6H), 7.85-7.75 (m, 9H), 4.08 (q, 4H), 3.52 (s, 12H), 3.04 (s, 6H), 1.92 (t, 6H), -2.58 (s, 2H) -2.99, -3.18 (each br s, 2H).
29. 3): 10.18 (s, 2H), 9.92 (s, 1H), 9.33, 8.99 (each d, 4H), 8.91 (s, 1H), 8.82 (s, 4H), 8.68, 8.51 (each d, 2H), 8.28-8.12 (m, 6H), 7.82-7.68 (m, 10H), 4.02 (q, 4H), 3.60 (s, 12H), 3.09 (s, 6H), 1.83 (t, 6H), -2.77 (s, 2H) -3.10, -3.29 (each br s, 2H).
30. Wennerström, O.; Ericsson, H.; Raston, I.; Svensson, S.; Pimlott, W. Tetrahedron Lett., 1989, 30, 1129.