Expanding the porphyrin π-system by fusion with anthracene

Organic Letters

Volumn 10, Issue 18, 2008, Pages 3945-3947

  Davis, Nicola K S ^a   Pawlicki, Miłosz ^a   Anderson, Harry L ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61349100699     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801500b     Document Type: Article

References (24)

1. (a) Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718-747.
2. (b) Müllen, K.; Rabe, J. P. Acc. Chem. Res. 2008, 41, 511-520.
3. (a) Tsuda, A.; Furuta, H.; Osuka, A. Angew. Chem., Int. Ed. 2000, 39, 2549-2552.
4. (b) Tsuda, A.; Osuka, A. Science 2001, 293, 79-82.
5. (a) Barloy, L.; Dolphin, D.; Dupré, D.; Wijesekera, T. P. J. Org. Chem. 1994, 59, 7976-7985.
6. (b) Richeter, S.; Jeandon, C.; Gisselbrecht, J.-P.; Ruppert, R.; Callot, H. J. J. Am. Chem. Soc. 2002, 124, 6168-6179.
7. (c) Fox, S.; Boyle, R. W. Chem. Commun. 2004, 1322-1323.
8. (d) Shen, D.-M.; Liu, C.; Chen, Q.-Y. Chem. Commun. 2005, 4982-4984.
9. (e) Hao, E.; Fronczek, F. R.; Vincente, M. G. H. J. Org. Chem. 2006, 71, 1233-1236.
10. (f) Shen, D.-M.; Liu, C.; Chen, Q.-Y. J. Org. Chem. 2006, 71, 6508-6511.
11. (g) Fox, S.; Boyle, R. W. Tetrahedron 2006, 62, 10039-10054.
12. (a) Gill, H. S.; Marmjanz, M.; Santamaria, J.; Finger, I.; Scott, M. J. Angew. Chem., Int. Ed. 2004, 43, 485-490.
13. (b) Cammidge, A. N.; Scaife, P. J.; Berber, G.; Hughes, D. L. Org. Lett. 2005, 7, 3413-3416.
14. (c) Tanaka, M.; Hayashi, S.; Eu, S.; Umeyama, T.; Matano, Y.; Imahori, H. Chem. Commun. 2007, 2069-2071.
15. Yamane, O.; Sugiura, K.; Miyasaka, H.; Nakamura, K.; Fujimoto, T.; Nakamura, K.; Kaneda, T.; Sakata, Y.; Yamashita, M. Chem. Lett. 2004, 33, 40-41.
16. Kurotobi, K.; Kim, K. S.; Noh, S. B.; Kim, D.; Osuka, A. Angew. Chem., Int. Ed. 2006, 45, 3944-3947.
17. The idea of synthesizing anthracene-fused porphyrins was suggested by: Yen T. F. In The Role of Trace Metals in Petroleum; Yen, T. F., Ed.; Ann Arbor Scientific: Ann Arbor, 1975; pp 1-30. We thank a reviewer for drawing this article to our attention.
18. Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676-12677.
19. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685-4696.
20. Krivokapic, A.; Anderson, H. L. Org. Biomol. Chem. 2003, 1, 3639-3641.
21. 3 oxidation of the 1:4 mixture of 5b and 8 and no unreacted 5b is detected in the product mixture, but if 1b is formed in this reaction it appears to be so insoluble that it is lost during chromatography; 1b was not isolated.
22. Rio, Y.; Rodríguez-Morgade, M.; Torres, T. Org. Biomol. Chem. 2008, 6, 1877-1894.
23. MacDonald, I. J.; Dougherty, T. J. J. Porphyrins Phthalocyanines 2001, 5, 105-129.
24. Senge, M. O.; Fazekas, M.; Notaras, E. G. A.; Blau, W. J.; Zawadzka, M.; Locos, O. B.; Mhuircheartaigh, E. M. N. Adv. Mater. 2007, 19, 2737-2774.