Synthesis of Perylene-3,4-mono(dicarboximide)−Fullerene C60 Dyads as New Light-Harvesting Systems - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2008

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

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Jérôme Baffreau
  • Fonction : Auteur
Lucie Ordronneau
  • Fonction : Auteur
Stéphanie Leroy-Lhez
  • Fonction : Auteur
Piétrick Hudhomme

Résumé

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.

Domaines

Chimie

Dates et versions

hal-03027811 , version 1 (27-11-2020)

Identifiants

Citer

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, 2008, 73 (16), pp.6142 - 6147. ⟨10.1021/jo800804z⟩. ⟨hal-03027811⟩
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