Generation of singlet oxygen with anionic aluminum phthalocyanines in water

The dependence of the quantum yield of photogeneration of singlet oxygen with aluminum sulfophthalocyanines on the degree of their sulfonation was studied. Experiments showed that Fotosens preparation containing, on the average, about three sulfo groups in the macroring in aqueous buffer solution (pH 7.4) exists in the monomeric form and sensitizes singlet oxygen with a quantum yield phi(Delta) 0.42 +/- 0.06. Aluminum tetra-4-sulfophthalocyanine forms dimers, and correspondingly phi(Delta) is lower: 0.22 +/- 0.03. Sulfonated aluminum phthalocyanine containing, on the average, about two sulfo groups in the macroring is aggregated to a significant extent. Addition of Triton X-100 detergent results in partial deaggregation of the dye, and phi(Delta) increases from similar to0.01 to 0.15 +/- 0.02. In the series including previously unknown aluminum phthalocyanines containing residues of phosphonic acids or their esters, and also aluminum and zinc octacarboxyphthalocyanines, the influence of the dye structure on the quantum yield of generation of singlet oxygen suggests participation of axial hydroxy groups in associate formation. These associates are not manifested spectroscopically and generate singlet oxygen inefficiently. The quantum yields phi(Delta) for the monomers and associates are 0.3 and 0.1, respectively.