9
views
0
recommends
+1 Recommend
0 collections
    0
    shares
      • Record: found
      • Abstract: not found
      • Article: not found

      Synthesis of Perylene-3,4-mono(dicarboximide)−Fullerene C60Dyads as New Light-Harvesting Systems

      , , ,
      The Journal of Organic Chemistry
      American Chemical Society (ACS)

      Read this article at

      ScienceOpenPublisherPubMed
      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          Fullerene C 60-perylene-3,4-mono(dicarboximide) (C 60-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 C 60-PMI dyad. Cyclic voltammetry showed that the first one-electron reduction process unambiguously occurs onto the C 60 moiety and the following two-electron process corresponds to the concomitant second reduction of C 60 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 C 60-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 C 60 playing the role of the acceptor in the photoactive layer.

          Related collections

          Author and article information

          Journal
          The Journal of Organic Chemistry
          J. Org. Chem.
          American Chemical Society (ACS)
          0022-3263
          1520-6904
          August 2008
          August 2008
          : 73
          : 16
          : 6142-6147
          Article
          10.1021/jo800804z
          18642952
          96a87e65-24b5-4b30-adcc-873b94c6a776
          © 2008
          History

          Comments

          Comment on this article