Synthesis of adj-diazuliporphyrins

ORGN 376

Zhenjun Zhang, zzhang@ilstu.edu and Timothy D. Lash, tdlash@ilstu.edu. Department of Chemistry, Illinois State University, Normal, IL 61790
Carbaporphyrins, porphyrin analogues in which one or more of the pyrrole subunits are replaced by carbocyclic rings, have been widely studied but few examples of dicarbaporphyrins have been reported. In this project, a novel dicarbaporphyrinoid system with two adjacent azulene subunits was synthesized by the ‘2+2' MacDonald methodology. This involved the condensation of dipyrrylmethanes with a diazulene dialdehyde, following oxidation, and protonation to afford the corresponding dihydrobromide salt. Proton NMR spectroscopy shows that the diazuliporphyrin system has borderline diatropic characteristics.

 

Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008