The syntheses and coordination chemistry of the oxycarbahemiporphyrazines

INOR 318

Natalie V. Barone, nb18@uakron.edu1, William S. Durfee, durfeews@buffalostate.edu2, and Christopher J. Ziegler, ziegler@uakron.edu1. (1) Department of Chemistry, University of Akron, Akron, OH 44325-3601, (2) Department of Chemistry, Buffalo State College, Buffalo, NY 14222
The metal binding chemistry of the carbaporphyrins, where one or more of the internal nitrogen positions of the macrocycle are replaced with carbon, is a rapidly growing area of research in metalloporphyrin chemistry. We have been recently investigating the chemistry of the carbahemiporphyrazines, anti-aromatic phthalocyanine analogs where one or more isoindolene rings has been replaced with benzene rings. In this presentation, we report the synthesis of the oxycarbahemiporphyrazines, where either phenol or resorcinol is incorporated into a phthalocyanine ring. Due to the redox activity of the phenol or resorcinol, these macrocycles are potentially aromatic upon oxidation in a fashion similar to that seen in the oxybenziporphyrins. As in the carbahemiporphyrazines, these rings can bind metal ions, forming novel organometallic interactions at the core of the ring.