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

•Synthesis of novel BODIPY- C60 and monostyryl- BODIPY- C60 dyads via Bingel Cyclopropanation.•Investigation of photochemical and photophysical properties.•Heavy atom free triplet photosensitizers.•High singlet oxygen generation capacities as a result of intramolecular spin converter, fullerene- C60.

Unsubstituted and monostyryl BODIPY- C60 dyads that show absorption in the visible region have been prepared via Bingel Cyclopropanation between BODIPY derivatives and C60 and characterized via mass, 1H and 13C NMR spectroscopy as novel heavy atom free triplet photosensitizers to generate 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 (C60), thus ensuring intersystem crossing and population of the triplet state. We found that the BODIPY- C60 dyads can be used as photocatalysts that is singlet oxygen (1O2). In the photooxidation of DPBF the 1O2 photosensitizing abilities of the C60 dyads are greater than the conventional triplet sensitizer methylene blue.

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