An Extremely Air-Stable 19π Porphyrinoid

J Am Chem Soc. 2015 Jul 29;137(29):9258-61. doi: 10.1021/jacs.5b05781. Epub 2015 Jul 15.

Abstract

A one-electron reduced species of a cationic phosphorus(V) tetraazaporphyrin complex has been isolated as an air-stable solid. Cyclic voltammetry and magnetic measurements showed the species to be a neutral π radical, and the solid state structure was elucidated by single crystal X-ray diffraction analysis. Magnetic circular dichroism spectroscopy and theoretical calculations also support a 19π electron conjugated electronic circuit.