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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.
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.