Preparation of NDI-BODIPY Based Photo Catalyzers for Green LED Irradiated Synthesis of Juglone

Abstract

Photochemistry related studies have been driven by with the application of new types of photocatalysis. Lately boron-dipyrromethene (BODIPY) as distinguished chromophore with exceptional photophysical and chemical features has emerged as a viable photosensitizer. Within this context, three new NDI-BODIPY triads (8-10) were synthesized/ characterized and used to investigate the efficiencies of singlet oxygen generation and oxidation of 1,5-dihydroxynapthalene to juglone under visible light. Singlet oxygen generation was determined both via indirect method by using 1,3-diphenylisobenzofuran as trap molecule and from the characteristic O-1(2) phosphorescence at 1270 nm. Also, NDI with BODIPY dyes bearing bromine and iodine atoms were shown to be highly active photocatalysts in which the activities are comparable or higher to the readily available commercial systems where 36% (9) and 66% (10) juglone production was achieved under 15 min. This work may emphasize good example of applying NDI-BODIPY based triads as photocatalysts for a series of important organic transformations.