Facile Synthesis of 9,10,19,20‐Tetraarylporphycenes

Abstract

AbstractA simple route was developed for the synthesis of 9,10,19,20‐tetraarylporphycenes by combining both McMurry and oxidative synthetic strategies and using readily available precursors. The desired 5,6‐diaryldipyrroethenes, which were prepared in multigram quantities over two steps, were used to prepare 9,10,19,20‐tetraarylporphycenes under mild acid‐catalyzed conditions. As 5,6‐diaryldipyrroethene precursors can easily be prepared in multigram quantities, this method is useful for the preparation of meso‐tetrarylporphycenes that contain different aryl substituents. The molecular structures of these macrocycles were determined by HRMS analysis as well as 1D and 2D NMR studies. The tetraarylporphycenes exhibited a strong Soret band at approximately 380 nm and three Q bands in the region of 580–655 nm. The tetraarylprophycenes are reasonably fluorescent and stable under redox conditions.