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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.
Two metal tetrapyrroles containing gallium, gallium hydroxyl tetratolylporphyrin and 13(2)-demethoxycarbonyl- (gallium hydroxyl)methyl pheophorbide a (Ga-(OH)-chlorin), were synthesized from their respective free bases using Ga(III)-acetylacetonate in a phenol melt. Their photophysical properties were investigated and the quantum yields of different monomolecular deactivation processes were determined. For Ga-(OH)-porphyrin S-2-fluorescence was observed and quantified. In contrast. for Ga-(OH)-chlorin no S-2-fluorescence was observed. Both compounds should be useful as efficient photosensitizers in photodynamic therapy.