1047682-76-7Relevant academic research and scientific papers
Synthesis of perylene-3,4-mono(dicarboximide)-fullerene C60 dyads as new light-harvesting systems
Baffreau, Jerome,Ordronneau, Lucie,Leroy-Lhez, Stephanie,Hudhomme, Pietrick
, p. 6142 - 6147 (2008/12/22)
(Graph Presented) Fullerene C60-perylene-3,4-mono(dicarboximide) (C60-PMI) dyads 1-3 were synthesized in the search for new light-harvesting systems. The synthetic strategy to the PMI intermediate used a cross-coupling Suzuki reaction for the introduction of a formyl group in the ortho, meta, or para position. Subsequent 1,3-dipolar cycloaddition with C 60 led to the target C60-PMI dyad. Cyclic voltammetry showed that the first one-electron reduction process unambiguously occurs onto the C60 moiety and the following two-electron process corresponds to the concomitant second reduction of C60 and the first reduction of PMI. A quasi-quantitative quenching of fluorescence was shown in dyads 1-3, and an intramolecular energy transfer was suggested to occur from the PMI to the fullerene moiety. These C60-PMI dyads constitute good candidates for future photovoltaic applications with expected well-defined roles for both partners, i.e., PMI acting as a light-harvesting antenna and C60 playing the role of the acceptor in the photoactive layer.
