Titre | Synthesis of Perylene-3,4-mono(dicarboximide)−Fullerene C60 Dyads as New Light-Harvesting Systems |
Type de publication | Article de revue |
Auteur | Baffreau, Jérôme, Ordronneau, Lucie, Leroy-Lhez, Stéphanie, Hudhomme, Piétrick |
Type | Article scientifique dans une revue à comité de lecture |
Année | 2008 |
Langue | Anglais |
Date | 2008/08 |
Numéro | 16 |
Pagination | 6142 - 6147 |
Volume | 73 |
Titre de la revue | The Journal of Organic Chemistry |
ISSN | 0022-3263 |
Résumé en anglais | 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. |
URL de la notice | http://okina.univ-angers.fr/publications/ua1933 |
DOI | 10.1021/jo800804z |
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