13 Organic photochemistry

Abstract

This review covers the literature during publication year 2003 concerning organic photochemistry. The general areas of photochemical applications in organic synthesis and mechanistic studies are both covered. This review is selective rather than comprehensive, due to the large volume of publications in this field. Biological photochemistry is not covered.

Of particular note in 2003 is the first report of single crystal absolute asymmetric photocyclization. Chiral crystals of 1,2-bis(5-m-formylphenyl-2-methyl-3-thienyl)perfluorocyclopentene underwent highly enantioselective photocyclization upon irradiation with ultraviolet light, while irradiation of the compound in solution gave a racemic mixture. Irradiation of the crystals with visible light reversed the reaction. The first intermolecular dimerization of fullerene in solution was achieved using a melamine derivative as a template to promote hydrogen bonding between two fullerene–barbituric acid derivatives. Donor–acceptor functionalized substrates and biphenanthrylidenes were developed as light-driven molecular motors.