Versatile '3 + 1' syntheses of acenaphthoporphyrins, a new family of highly conjugated tetrapyrroles

Tetrahedron Letters

Volumn 37, Issue 28, 1996, Pages 4873-4876

  Chandrasekar, Pushpa ^a   Lash, Timothy D ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; POLYMERIZATION; SYNTHESIS; TEMPERATURE; ULTRAVIOLET SPECTROSCOPY;

EID: 0030575414     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00998-7     Document Type: Article

References (33)

1. 1. Porphyrins and Metalloporphyrins; Smith, K.M., ed.; Elsevier, Amsterdam; 1975.
2. 2. Phthalocyanines: Properties and Applications, Leznoff, C.C., ed.; VCH Publishers, Vol. 1-3; 1990-1993.
3. 3. In photodynamic therapy, porphyrins and phthalocyanines have been exploited as efficient photosensitizers. Due to the greater tissue penetration by laser light at higher wavelengths, red shifted chromophores are of particular value in this area. See: Brown, S.B.; Truscott, T.G. Chem. Br. 1993, 29, 955; Bonnett, R. Chem. Soc. Rev. 1995, 24, 19.
4. 3. In photodynamic therapy, porphyrins and phthalocyanines have been exploited as efficient photosensitizers. Due to the greater tissue penetration by laser light at higher wavelengths, red shifted chromophores are of particular value in this area. See: Brown, S.B.; Truscott, T.G. Chem. Br. 1993, 29, 955; Bonnett, R. Chem. Soc. Rev. 1995, 24, 19.
5. 4. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177-273. Franck, B.; Nonn, A. Angew. Chem. Int. Ed. Eng. 1995, 34, 1795.
6. 4. Sessler, J.L.; Burrell, A.K. Top. Curr. Chem. 1991, 161, 177-273. Franck, B.; Nonn, A. Angew. Chem. Int. Ed. Eng. 1995, 34, 1795.
7. 5. E.g.: Montforts, F.-P.; Gerlach, B.; Hoper, F. Chem. Rev. 1994, 94, 327.
8. 6. a. Clezy, P.S.; Fookes, C.J.R.; Mirza, A.H. Aust. J. Chem. 1977, 30, 1337.
9. b. Clezy, P.S.; Mirza, A.H. Aust. J. Chem. 1982, 35, 197.
10. c. Bonnett, R.; McManus, K.A. J. Chem. Soc., Chem. Commun. 1994, 1129.
11. 7. Lash, T.D. Energy Fuels 1993, 7, 166.
12. 8. a. Lash, T.D.; Roper, T.J. Tetrahedron Lett. 1994, 35, 7715.
13. b. Lash, T.D.; Denny, C.P. Tetrahedron 1995, 51, 59.
14. 9. a. Lash, T.D.; Novak, B.H. Angew. Chem. Int. Ed. Engl. 1995, 34, 683.
15. b. Lash, T.D.; Novak, B.H. Tetrahedron Lett. 1995, 36, 4381.
16. c. Freemantle, M. C&E News 1994, 72 (39), 25-27.
17. 10. Lin, Y.; Lash, T.D. Tetrahedron Lett. 1995, 36, 9441.
18. 11. Lash, T.D.; Novak, B.H.; Lin, Y. Tetrahedron Lett. 1994, 35, 2493.
19. 12. Ono, N.; Hironaga, H.; Simizu, K.; Ono, K.; Kuwano, K.; Ogawa, T. J. Chem. Soc., Chem. Commun. 1994, 1019.
20. 13. Iida, H.; Kajiyama, I.; Yamada, K. Nippon Kagaku Kaishi 1972, 137. Chem. Abstr. 1972, 76, 99395m.
21. 13. Iida, H.; Kajiyama, I.; Yamada, K. Nippon Kagaku Kaishi 1972, 137. Chem. Abstr. 1972, 76, 99395m.
22. 14. a. Arsenault, G.P.; Bullock, E.; MacDonald, S.F. J. Am. Chem. Soc. 1960, 82, 4384.
23. b. Cavaleiro, J.A.S.; Rocha Gonsalves, A.M. d'A.; Kenner, G.W.; Smith, K.M. J. Chem. Soc., Perkin Trans. I 1974, 1771.
24. c. Lash, T.D.; Catarello, J.J. Tetrahedron 1993, 49, 4159.
25. 15. a. Broadhurst, M.J.; Grigg, R.; Johnson, A. W. J. Chem. Soc. (C) 1971, 3681.
26. b. Boudif, A.; Momenteau, M. J. Chem. Soc., Chem. Commun. 1994, 2069.
27. c. Lash, T.D. Angew. Chem. Int. Ed. Eng. 1995, 34, 2533.
28. 16. An alternative strategy for the "3 + 1" synthesis of porphyrins, using 2,5-bis-(dimethylaminomethyl)pyrroles as the key intermediates, was recently reported: Nguyen, L.T.; Senge, M.O.; Smith, K.M. J. Org. Chem. 1996, 61, 998.
29. 2), 7.47-7.57 (6H, m, 6 x acenaphthylene-H), 9.12 (1H, br), 11.15 (2H, br) (3 x NH). Tripyrranes 10b and 10c could not be recrystallized and these vacuum dried powders were used without further purification.
30. 18. Vogel, E.; Jux, N.; Rodriguez-Val, E.; Lex, J.; Schmickler, H. Angew. Chem. Int. Ed. Engl., 1990, 29, 1387.
31. 4 + H: 785.3128. Found: 785.3132.
32. 20. Miller, R.; Olsson, K. Acta Chem Scand. B 1981, 35, 303. Dolphin, D.: Paine, J.B. III; Woodward, R.B. J. Org. Chem. 1976, 41, 2830.
33. 20. Miller, R.; Olsson, K. Acta Chem Scand. B 1981, 35, 303. Dolphin, D.: Paine, J.B. III; Woodward, R.B. J. Org. Chem. 1976, 41, 2830.