Synthesis and electronic absorption studies of novel (trifluoromethyl)phenoxy-substituted phthalocyanines

The reaction of 4-[4-(trifluoromethyl)phenoxy]phenol with 4-nitrophthalonitrile in the presence of K2CO3 leads to formation of 4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]phthalonitrile. Tetrakis[4-[4-(trifluoromethyl)phenoxy]phenoxy]-substituted metal-free phthalocyanine was achieved by tetramerization of the phthalonitrile in 2-(dimethylamino)ethanol, whereas metallophthalocyanines were prepared in the presence of zinc, cobalt, or copper salts. These compounds show high solubility in weakly and medium polar solvents, in strongly polar solvents (dimethylformamide, dimethylsulfoxide), and in aromatic hydrocarbons (toluene, benzene). The new phthalocyanines were characterized by elemental analyses, H-1 nuclear magnetic resonance (NMR), C-13 NMR, F-19 NMR, ultraviolet-visible (UV-Vis), Fourier-transform infrared (FT-IR), and mass spectroscopic methods.