@article{KatterleHolzwarthJesorka2006, author = {Katterle, Martin and Holzwarth, Alfred R. and Jesorka, Aldo}, title = {A Heck-type coupling for the synthesis of novel bridged metallochlorin-fullerene C-60 dyads}, issn = {1434-193X}, doi = {10.1002/ejoc.200500494}, year = {2006}, abstract = {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.}, language = {en} }