Synthesis, characterization and aggregation properties of water-soluble metal-free and metallophthalocyanines peripherally tetra-substituted with 2-[2-(dimethylamino)ethoxy]ethoxy moiety

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, THF and DMSO, metal-free phthalocyanine showed aggregation in DMSO. The new compounds have been characterized by using UV–vis, IR, 1H-NMR, elemental analysis, MS spectroscopic data.

► Synthesis and characterization of metal-free and metallophthalocyanines. ► Synthesis and characterization of water-soluble metal-free and metallophthalocyanines. ► Investigation of aggregation properties of metal-free and metallophthalocyanines in different solvents.