Bis-Anthracene Fused Porphyrin as an Efficient Photocatalyst: Facile Synthesis and Visible-Light-Driven Oxidative Coupling of Amines

Chemistry. 2020 Dec 9;26(69):16497-16503. doi: 10.1002/chem.202003398. Epub 2020 Nov 11.

Abstract

Development of high-performance photocatalysts for the conversion of amines is of great importance, but has remained a challenging task. Here, a bis-anthracene fused porphyrin (AFP) was synthesized in a high yield by a facile synthetic protocol, which involves a Suzuki coupling for the conjugation of two anthracene groups with a porphyrin ring, followed by oxidative cyclodehydrogenation. When serving as a photocatalyst, AFP exhibits an outstanding photocatalytic performance for the visible-light-induced aerobic oxidation of amines to imines at ambient conditions. Density functional theory calculations revealed that the low energy band gap, caused by the large planar and π-extended porphyrin structure of AFP, contributed to its high photocatalytic performance.

Keywords: cyclodehydrogenation; energy band gaps; oxidation of amines; photocatalysis; porphyrins.