Preparation of BODIPY- fullerene and monostyryl BODIPY-fullerene dyads as heavy atom free singlet oxygen generators

Abstract

Unsubstituted and monostyryl BODIPY-C-60 dyads that show absorption in the visible region have been prepared via Bingel Cyclopropanation between BODIPY derivatives and C-60 and characterized via mass, H-1 and C-13 NMR spectroscopy as novel heavy atom free triplet photosensitizers to geherate singlet oxygen. The new photosensitizers contain one and two light-harvesting antennas as well as associated different absorption wavelengths, resulting in high singlet oxygen generation. The panchromatic excitation energy harvested by the BODIPY moieties is funneled into a spin converter (C-60), thus ensuring intersystem crossing and population of the triplet state. We found that the BODIPY-C-60 dyads can be used as photocatalysts that is singlet oxygen (O-1(2)). In the photooxidation of DPBF the O-1(2) photosensitizing abilities of the C-60 dyads are greater than the conventional triplet sensitizer methylene blue. (C) 2017 Elsevier Ltd. All rights reserved.