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

•The synthesis of 4-(5-chloro-2-(2,4-dichlorophenoxy)phenol) substituted metal-free, zinc(II) and lead (II) phthalocyanines.•The structural characterization of the novel phthalocyanines was performed by a combination of different spectroscopic techniques.•The photophysical and photochemical properties of the novel phthalocyanines were investigated.

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, 1H 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.

Graphical abstractDownload high-res image (188KB)Download full-size image