Synthesis, characterisation, photophysical and photochemical properties of free-base tetra-(5-chloro-2-(2,4-dichlorophenoxy) phenoxy)phthalocyanine and respective zinc(II) and lead(II) complexes

In this study, novel peripherally tetra-(5-chloro-2-(2,4-dichlorophenoxy)phenol) substituted metal-free (4), zinc(II) (5) and lead(II) (6) phthalocyanine derivatives were synthesised. The novel phthalocyanines (4-6) were characterised by general spectroscopic methods such as IR, H-1 NMR, UV-vis, mass spectrometry and elemental analysis. Once the solubilities of the compounds were investigated, it was noticed that they have excellent solubility and did not tend to aggregation behaviour in common solvents. The photophysical and photochemical properties of novel phthalocyanines (4-6) were investigated in dimethysulfoxide. The effects of substituted 5-chloro-2-(2,4-dichlorophenoxy)phenoxy group and central metal ion [zinc(II)/lead(II)] on photophysical and photochemical properties of the novel phthalocyanines have also been examined, and the results were compared with unsubstituted zinc (II) phthalocyanine. According to photophysical and photochemical investigation results, it was observed that the novel phthalocyanines (4-6) have a potential for PDT application. (C) 2016 Elsevier B.V. All rights reserved.