Octaiodoporphyrin and Octaiodocorrole: Isolation of a Cis Porphyrin Tautomer

Abstract

Iodinated aromatics are excellent starting materials for further elaboration via transition-metal-catalyzed cross-coupling reactions. Considering the diverse applications of porphyrins and corroles - as photosensitizers in photodynamic therapy, dye sensitized solar cells, near-infrared dyes, gas sensors, nonlinear optical materials, and catalysts - the synthetic potential of β-polyiodinated or octaiodinated porphyrins and corroles may be considerable. As part of my doctoral studies, I have synthesized and structurally characterized the first examples of both β-octaiodinated porphyrins and β-octaiodinated corroles. Furthermore, a single-crystal X-ray structure of free base β-octaiodoporphyrin provided an example of a cis porphyrin tautomer, the long hypothesized intermediate of porphyrin NH tautomerism.