In this study, novel metal-free 2, cobalt 3 and copper 4 phthalocyanines were synthesized and characterized for the first time. These new phthalocyanines 2-4 were converted into water-soluble quaternized products 2a-4a by the reaction with methyl iodide. The quaternized complexes 2a-4a show excellent solubility in both organic and aqueous solutions which make them potential photosensitizer for use in PDT. Aggregation properties of metal-free and metallophthalocyanines were investigated at different concentrations in chloroform, dimethylsulfoxide, dimethylformamide, tetrahydrofuran and water. While all synthesized metallophthalocyanine complexes did not show aggregation in chloroform. THE and DMSO, metal-free phthalocyanine showed aggregation in DMSO. The new compounds have been characterized by using UV-vis, IR, H-1-NMR, elemental analysis, MS spectroscopic data. (C) 2011 Elsevier B.V. All rights reserved.