Synthesis and investigation of photodynamic therapy properties of new water soluble zinc phthalocyanines

The aim of this work is to synthesis, characterization and investigation of photodynamic therapy (PDT) properties of the new peripherally and non-peripherally tetra-substituted zinc phthalocyanines (2a, 3a, 5a ve 6a) and their water soluble quaterner derivates (2b, 3b, 5b ve 6b). In this work, compounds 1, 2, 4 and 5 were synthesized by using methods in literature. The substituted phthalonitriles 3 and 6 were synthesized by the reactions between 3-nitrophthalonitrile and 2-[3-(dimethylamino)phenoxy]ethanol (1) and 2-[3-(diethylamino)phenoxy]ethanol (4), respectively in dry DMF and in the presence of anhydrous potassium carbonate. The zinc phthalocyanines (2a, 3a, 5a and 6a) were synthesized by cyclotetramerization of phthalonitrile derivatives (2, 3, 5 and 6) in the presence of anhydrous Zn(CH3COO)2 in n-pentanol and DBU. Water soluble zinc phthalocyanines (2b, 3b, 5b and 6b) were synthesized from the reaction of corresponding zinc phthalocyanines (2a, 3a, 5a and 6a) with methyl iodide in chloroform at room temperature. The structures of the synthesized original compounds were identified by using elemental analysis, IR, 1H-NMR, 13C-NMR, UV-Vis ve MS spectroscopic data. In addition, the photophysical and photochemical properties of all zinc phthalocyanines (2a, 2b, 3a, 3b, 5a, 5b, 6a ve 6b), which are potential photosensitizer in photodynamic therapy, were investigated.