Synthesis of novel laterally-bridged pyropheophorbide a dimers

(Note: The full text of this document is currently only available in the PDF Version )

Andrei N. Kozyrev, James L. Alderfer, Thamarapu Srikrishnan and Ravindra K. Pandey


Abstract

Condensation of 132-oxopyropheophorbide a with benzene-1,2,4,5-tetramine produced a bis-quinoxaline-bridged symmetrical chlorin dimer and an unsymmetrical benzimidazole/pyrazine bridged analog. Spectroscopic data of the novel conjugated dimers show a significant perturbation of the extended bis-chlorin π-system in a coplanar arrangement.


References

  1. (a) M. R. Wasielewski, Chem. Rev., 1992, 92, 435 CrossRef CAS and references cited therein; (b) R. W. Wagner and J. S. Lindsey, J. Am. Chem. Soc., 1994, 116, 9759 CrossRef CAS; (c) J. L. Sessler, M. R. Johnson, T. Y. Lin and S. E. Greager, J. Am. Chem. Soc., 1988, 110, 3659 CrossRef CAS; (d) C. K. Chang and I. Abdalmuhdi, J. Org. Chem., 1983, 48, 5388 CrossRef CAS; (e) D. Gust and T. A. Moore, Science, 1989, 244, 35 CrossRef CAS; (f) R. K. Pandey, T. P. Forsyth, K. R. Gerzevske, J. L. Lin and K. M. Smith, Tetrahedron Lett., 1992, 33, 5515 CrossRef.
  2. (a) J. M. Lehn, Supramolecular Chemistry, VCH, Weinhein, 1995 Search PubMed; (b) The Photosynthetic Reaction Center, ed. J. R. Norris and J. Deisenhofer, Academic Press, San Diego, 1993 Search PubMed; (c) L. Jaquinod, D. J. Nurco, R. K. Pandey, M. O. Senge and K. M. Smith, Angew. Chem., Int. Ed. Engl., 1996, 35, 2496 Search PubMed.
  3. (a) M. J. Crossley and P. L. Burn, J. Chem. Soc., Chem. Commun., 1995, 1921 RSC; (b) M. J. Crossley and P. L. Burn, J. Chem. Soc., Chem. Commun., 1987, 39 RSC.
  4. (a) J. Jaquinod, M. O. Senge, R. K. Pandey, T. P. Forsyth and K. M. Smith, Angew. Chem., Int. Ed. Engl., 1996, 35, 1840 Search PubMed; (b) L. Jaquinod, D. J. Nurco, C. J. Medforth, R. K. Pandey, T. P. Forsyth, M. M. Olmstead and K. M. Smith, Angew. Chem., Int. Ed. Engl., 1996, 35, 1013 Search PubMed.
  5. A. N. Kozyrev, T. J. Dougherty and R. K. Pandey, Chem. Commun., in the press Search PubMed.
  6. P. Hynninen, Chemistry of Chlorophylls: Modifications, in Chlorophylls, ed. H. Scheer, CRC Press, Roca Raton, 1990 Search PubMed.
  7. A. N. Kozyrev, G. Zheng, C. Zhu, T. J. Dougherty, K. M. Smith and R. K. Pandey, Tetrahedron Lett., 1996, 37, 6431 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.