A Heck-type coupling for the synthesis of novel bridged metallochlorin-fullerene C-60 dyads
Journal article, 2006

A short and convenient synthesis of metallochlorin-C-60 dyads based on a Heck-type hetero coupling at the 3(2) position of a chlorin is described. p-Bromobenzaldehyde was treated with Zn-metalated 13(2)-demethoxycarbonylmethylpheophorbide a, using a palladium acetate/LiCl catalyst mixture under phase-transfer conditions in DMF at 70 degrees 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 C-60 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. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).

Author

M. Katterle

University of Potsdam

A. R. Holzwarth

Max Planck Institute

Aldo Jesorka

Chalmers, Chemical and Biological Engineering, Physical Chemistry

European Journal of Organic Chemistry

1434-193X (ISSN)

2 414-422

Subject Categories

Chemical Sciences

DOI

10.1002/ejoc.200500494

More information

Latest update

3/19/2018