Synthesis and Properties of Phosphaporphyrin

Abstract

Core-modified porphyrins are one of the porphyrin analogues, in which at least one core nitrogen atom is replaced by another atom. Although the chemistry of core-modified porphyrins has attracted much attention, phosphorous-containing porphyrins, namely "phosphaporphyrins", have not been prepared. Here we report the first synthesis of phosphaporphyrin and its aromaticity as well as optical and electrochemical properties. A phosphaporphyrin was synthesized via acid-promoted condensation of phosphatripyrrane with 2,5-bis[hydroxy(phenyl)methyl]thiophene. The NMR and UV-vis absorption spectra, and CV has revealed that the phosphaporphyrin possesses a considerable aromaticity and a relatively narrow HOMO-LUMO energy gap.