Novel perfluoroalkyl phthalocyanine metal derivatives: Synthesis and photodynamic activities

Novel perfluoroalkyl phthalocyanine metal derivatives with four perfluorobutyl or four perfluorohexyl groups were synthesized by a two-step procedure starting from 4-iodophthalonitrile; the preparation of the key intermediate 4-(perfluorohexyl)phthalonitrile was optimized. Values of fluorescence quantum yield in ethanol of 0.11 and 0.38 were obtained for zinc(II) tetra (perfluorobutyl)phthalocyanine and zinc(II) tetra (perfluorohexyl) phthalocyanine, respectively. The photodynamic activities of two, zinc (II) phthalocyanine derivatives upon both HL-60 leukemic cells and A375 melanotic cancer cells in vitro were investigated revealed that the cell viability was slightly better in the case of HL-60 than A375.