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Article dans une revue

Synthesis of Perylene-3,4-mono(dicarboximide)−Fullerene C60 Dyads as New Light-Harvesting Systems

Abstract :

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 C60 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.

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Soumis le : vendredi 27 novembre 2020 - 12:28:00
Dernière modification le : jeudi 9 décembre 2021 - 15:46:05

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Jérôme Baffreau, Lucie Ordronneau, Stéphanie Leroy-Lhez, Piétrick Hudhomme. Synthesis of Perylene-3,4-mono(dicarboximide)−Fullerene C60 Dyads as New Light-Harvesting Systems. Journal of Organic Chemistry, American Chemical Society, 2008, 73 (16), pp.6142 - 6147. ⟨10.1021/jo800804z⟩. ⟨hal-03027811⟩



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