Preparation, characterization and photophysicochemical properties of novel tetra 7-(diethyl 2-methylmalonatoxy)-3-(p-oxyphenyl)coumarin-substituted zinc(II) and indium(III)chloride phthalocyanines

• Tetra coumarin-substituted zinc(II) and indium(III)chloro phthalocyanines were synthesized.
• The photophysicochemical properties of four new phthalocyanines were investigated.
• All these phthalocyanines can promise as photosensitizers for PDT applications.

In this study, 7-(diethyl 2-methylmalonatoxy)-3-[p-(3,4-dicyanophenoxy)phenyl]coumarin (3), 7-(diethyl 2-methylmalonatoxy)-3-[p-(2,3-dicyanophenoxy)phenyl]coumarin (4) and their related peripheral and non-peripheral tetra substituted zinc(II) (3a and 4a) and indium(III)chloride (3b and 4b) phthalocyanine derivatives were prepared for the first time. The novel phthalonitrile (3 and 4) and phthalocyanine (3a-b and 4a-b) compounds were characterized by elemental analyses and different spectroscopic techniques such as FT-IR, UV–vis, 1H NMR and MALDI-TOF mass. The spectral, photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of these novel phthalocyanines were investigated in dimethylsulfoxide solutions. The fluorescence quenching behaviors of the studied zinc(II) phthalocyanines (3a and 4a) by 1,4-benzoquinone were also determined.

The novel phthalocyanines tetra-substituted with four coumarinoxy-malonester groups were synthesized. The photophysical and photochemical properties were also examined for determination of their photosensitizer abilities. These phthalocyanines can promise as candidates for treatment of cancer by PDT technique according to the obtained results.Figure optionsDownload as PowerPoint slide