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A Heck-Type Coupling for the Synthesis of Novel Bridged Metallochlorin–Fullerene C60 Dyads

  1. Martin Katterle1,
  2. Alfred R. Holzwarth2,
  3. Aldo Jesorka3

Article first published online: 27 OCT 2005

DOI: 10.1002/ejoc.200500494

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2006, Issue 2, pages 414–422, January 2006

Additional Information

How to Cite

Katterle, M., Holzwarth, A. R. and Jesorka, A. (2006), A Heck-Type Coupling for the Synthesis of Novel Bridged Metallochlorin–Fullerene C60 Dyads. Eur. J. Org. Chem., 2006: 414–422. doi: 10.1002/ejoc.200500494

Author Information

  1. 1

    Institute of Biology and Analytical Biochemistry, University of Potsdam, K.-Liebknecht-Str. 24–25, 14476 Potsdam/Golm, Germany

  2. 2

    Max-Planck-Institut für Bioanorganische Chemie, P. O. Box 10 13 65, 45413 Mülheim/Ruhr, Germany

  3. 3

    Department of Chemistry and Bioscience, Chalmers University of Technology, Kemivägen 10, 41296 Gothenburg, Sweden

Publication History

  1. Issue published online: 2 JAN 2006
  2. Article first published online: 27 OCT 2005
  3. Manuscript Received: 5 JUL 2005

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Keywords:

  • Electron transfer;
  • Fullerenes;
  • Heck reaction;
  • Chlorin;
  • Dyads

Abstract

A short and convenient synthesis of metallochlorin–C60 dyads based on a Heck-type hetero coupling at the 32 position of a chlorin is described. p-Bromobenzaldehyde was treated with Zn-metalated 132-demethoxycarbonylmethylpheophorbide a, using a palladium acetate/LiCl catalyst mixture under phase-transfer conditions in DMF at 70 °C. The resulting asymmetric olefin was obtained in a high trans/cis ratio. The desired trans isomer was separated and subsequently transformed into a donor–acceptor dyad by a 1,3-dipolar cycloaddition to C60 in the presence of sarcosine in refluxing toluene. The resulting dyads are expected to undergo efficient photoinduced electron transfer and can potentially be utilized in solar energy conversion devices. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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