Tunable meso -tetraphenyl-alkyloxazolo-chlorins and -bacteriochlorins

Organic Letters

Volumn 13, Issue 9, 2011, Pages 2380-2383

  Ogikubo, Junichi ^a   Brückner, Christian ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIOCHLORIN; CHLORIN; OXAZOLE DERIVATIVE; PORPHYRIN;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

ALKYLATION; MOLECULAR STRUCTURE; OXAZOLES; PORPHYRINS;

EID: 79955582813     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2006264     Document Type: Article

References (33)

1. The ′optical window is between 600 and 1300 nm; the wavelength of maximum penetration of breast tissue is 725 nm: Cerussi, A. E.; Berger, A. J.; Bevilacqua, F.; Shah, N.; Jakubowski, D.; Butler, J.; Holcombe, R. F.; Tromberg, B. J. Acad. Radiol. 2001, 8, 211-218
2. For example, see: Artificial Photosynthesis & Solar Fuels thematic issue of Acc. Chem. Res. 2009, 42, 1859 - 2029.
3. Chlorophylls; Scheer, H., Ed.; CRC: Boca Raton, FL, 1991.
4. Sessler, J. L.; Weghorn, S. Expanded, Contracted & Isomeric Porphyrins; Pergamon Press: New York, NY, 1997.
5. The Porphyrin Handbook, Vol. 2-Heteroporphyrins, Expanded Porphyrins and Related Macrocycles; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 2.
6. Fox, S.; Boyle, R. W. Tetrahedron 2006, 62, 10039-10054
7. For recent examples, see: Jiao, C. J.; Huang, K. W.; Guan, Z. P.; Xu, Q. H.; Wu, J. S. Org. Lett. 2010, 12, 4046-4049
8. Diev, V. V.; Hanson, K.; Zimmerman, J. D.; Forrest, S. R.; Thompson, M. E. Angew. Chem., Int. Ed. 2010, 49, 5523-5526
9. Davis, N. K. S.; Thompson, A. L.; Anderson, H. L. J. Am. Chem. Soc. 2011, 133, 30-31
10. Akhigbe, J.; Zeller, M.; Brückner, C. Org. Lett. 2011, 13, 1322-1325
11. Flitsch, W. Adv. Heterocycl. Chem. 1988, 43, 73-126
12. Silva, A. M. G.; Tome, A. C.; Neves, M. G. P. M. S.; Silva, A. M. S.; Cavaleiro, J. A. S. J. Org. Chem. 2005, 70, 2306-2314
13. Sternberg, E. D.; Dolphin, D.; Brückner, C. Tetrahedron 1998, 54, 4151-4202
14. Chen, Y.; Li, G.; Pandey, R. K. Curr. Org. Chem. 2004, 8, 1105-1134
15. For a cross section of their work, see: Ptaszek, M.; Lahaye, D.; Krayer, M.; Muthiah, C.; Lindsey, J. S. J. Org. Chem. 2010, 75, 1659-1673
16. Ptaszek, M.; McDowell, B. E.; Taniguchi, M.; Kim, H.-J.; Lindsey, J. S. Tetrahedron 2007, 63, 3826-3839
17. Taniguchi, M.; Cramer, D. L.; Bhise, A. D.; Kee, H. L.; Bocian, D. F.; Holten, D.; Lindsey, J. S. New J. Chem. 2008, 32, 947-958
18. Mass, O.; Ptaszek, M.; Taniguchi, M.; Diers, J. R.; Kee, H. L.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Org. Chem. 2009, 74, 5276-5289
19. Krayer, M.; Ptaszek, M.; Kim, H.-J.; Meneely, K. R.; Fan, D.; Secor, K.; Lindsey, J. S. J. Org. Chem. 2010, 75, 1016-1039
20. Brückner, C.; Rettig, S. J.; Dolphin, D. J. Org. Chem. 1998, 63, 2094-2098
21. Samankumara, L. P.; Zeller, M.; Krause, J. A.; Brückner, C. Org. Biomol. Chem. 2010, 8, 1951-1965
22. McCarthy, J. R.; Jenkins, H. A.; Brückner, C. Org. Lett. 2003, 5, 19-22
23. McCarthy, J. R.; Melfi, P. J.; Capetta, S. H.; Brückner, C. Tetrahedron 2003, 59, 9137-9146
24. Akhigbe, J.; Ryppa, C.; Zeller, M.; Brückner, C. J. Org. Chem. 2009, 74, 4927-4933
25. Daniell, H. W.; Brückner, C. Angew. Chem., Int. Ed. 2004, 43, 1688-1691
26. McCarthy, J. R.; Hyland, M. A.; Brückner, C. Org. Biomol. Chem. 2004, 2, 1484-1491
27. Banerjee, S.; Hyland, M. A.; Brückner, C. Tetrahedron Lett. 2010, 51, 4505-4508
28. Khalil, G. E.; Daddario, P.; Lau, K. S. F.; Imtiaz, S.; King, M.; Gouterman, M.; Sidelev, A.; Puran, N.; Ghandehari, M.; Brückner, C. Analyst 2010, 135, 2125-2131
29. Crossley, M. J.; King, L. G. J. Chem. Soc., Chem. Commun 1984, 920-922
30. Gouterman, M.; Hall, R. J.; Khalil, G.-E.; Martin, P. C.; Shankland, E. G.; Cerny, R. L. J. Am. Chem. Soc. 1989, 111, 3702-3707
31. Brückner, C.; McCarthy, J. R.; Daniell, H. W.; Pendon, Z. D.; Ilagan, R. P.; Francis, T. M.; Ren, L.; Birge, R. R.; Frank, H. A. Chem. Phys. 2003, 294, 285-303
32. McCarthy, J. R.; Perez, M. J.; Brückner, C.; Weissleder, R. Nano Lett. 2005, 5, 2552-2556
33. Each diastereomer is chiral; thus they are each expected to exist as a racemic pair.