Synthesis, photophysical and photochemical properties of zinc phthalocyanines bearing fluoro-functionalized substituents

Abstract

In this study, the synthesis of phthalonitrile derivatives bearing fluoro-functionalized groups and their peripherally-tetra substituted zinc phthalocyanine complexes were reported. The phthalonitrile derivatives 2a-5a were prepared by nucleophilic substitution of 4-nitrophthalonitrile with 2-[3-(trifluoromethyl)phenoxy]ethanol, 2-{2-[3-(trifluoromethyl) phenoxy]ethoxy}ethanol, 2-(2,3,5,6-tetrafluorophenoxy)ethanol, 2-[2-(2,3,5,6-tetrafluorophenoxy)ethoxy]ethanol, respectively. Zinc phthalocyanines bearing fluoro-functionalized groups (2b-5b) were obtained from the corresponding phthalonitrile derivatives. The newly synthesized phthalocyanines displayed good solubility in organic solvents such as chloroform (CHCl3), dichloromethane (DCM), tetrahydrofuran (THF), toluene, dimethylformamide (DMF) and dimethylsulfoxide (DMSO). On the other hand, the singlet oxygen, photodegradation, fluorescence quantum yields and fluorescence lifetime of these complexes were determined in DMSO. The effects of the substitution with fluoro-functionalized groups on these parameters were also compared. (C) 2013 Elsevier B.V. All rights reserved.