Imaging Science and Photochemistry ›› 2014, Vol. 32 ›› Issue (5): 471-483.DOI: 10.7517/j.issn.1674-0475.2014.05.471

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Fullerene-bodipy Dyads and Triad Showing Strong Visible Light Absorption as Photocatalysts in Photocatalytic Oxidation of Sulfides

HUANG Ling, ZHAO Jianzhang   

  1. State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, P. R. China
  • Received:2014-07-12 Revised:2014-07-30 Online:2014-09-15 Published:2014-09-15

Abstract:

Fullerene C60-Bodipy dyads and triad were prepared with the Bodipy as visible light-harvesting antenna and the C60 unit as the intramolecular spin conventer. The dyads and triad show strong visible light absorption and long-lived triplet excited states, and were used as triplet photosensitizers for photocatalytic oxidation of sulfides. The triad shows broadband visible light-absorption, which is different from the conventional triplet photosensitizers. The photophysical properties of the triplet photosensitizers were studied with steady state and time-resolved spectroscopies. The compounds were used for photocatalytic oxidation of sulfides. The photocatalytic activity was greatly improved with the new organic triplet photosensitizers as compared with that of the conventional photocatalysts, such as the Ru(Ⅱ) bipyridine complexes. With electrochemical data, calculation of the free energy changes of the electron transfer between the photosensitizers and the substrates, electron spin resonance (ESR), it was confirmed that both singlet oxygen and superoxide radical anion were involved in the photocatalytic cycles and the intermolecular electron transfer and triplet energy transfer were improved with these new photosensitizers which show strong visible light-absorbing long-lived triplet excited states. These studies will be helpful for future design of new triplet photosensitizers as well as the application of organic photosensitizers in photocatalytic organic reactions.

Key words: Bodipy, fullerene, energy transfer, triplet photosensitizer, photocatalysis, sulfide