5-Perfluoroalkyldipyrromethanes and porphyrins derived therefrom

Abstract

Acid-catalyzed condensation of pyrrole and perfluoroalkyl aldehydes produced, in a single step, α,β-unsubstituted 5-perfluoroalkyldipyrromethanes, which were isolated and characterized for the first time. These dipyrromethanes were used as the key intermediates in the synthesis of trans-perfluroalkylporphyrins as well as meso-tetrakis(perfluoroalkyl)porphyrins. The two-step procedure described here provides access to a wide variety of porphyrins with trans perfluoroalkyl groups. Key words: 5-perfluoroalkyldipyrromethanes, perfluoroalkylporphyrins, electron-deficient porphyrins.