Synthesis, electrochemistry of metal-free, copper, titanium phthalocyanines and investigation of catalytic activity of cobalt, iron phthalocyanines on benzyl alcohol oxidation bearing 4-{2-[3-trifluoromethyl)phenoxy]ethoxy} groups

The synthesis, characterization of novel peripherally 4-{2-[3-trifluoromethyl)phenoxy]ethoxy} groups substituted metal-free, Cu(II), Ti(IV), Co(II), Fe(II) phthalocyanines have been reported for the first time in this study. All the new compounds were characterized by a combination of IR, H-1 NMR, C-13 NMR, mass and UV-vis spectroscopy techniques. Electrochemical studies of (TiOPc)-O-IV, H-2-Pc, (CuPc)-Pc-II were examined by using cyclic voltammetry (CV) and square wave voltammetry (SWV) techniques. Voltammetric analyses of phthalocyanines supported the proposed structure of the synthesized complexes. While H2Pc and Cul1Pc showed only ligand based reduction reactions, (TiOPc)-O-IV showed metal based and ligand based reduction reactions as expected. In addition, new Co(II) and Fe(II) phthalocyanine complexes (5,6) were investigated as a catalyst for the oxidation of benzyl alcohol. The influence of substrate/catalyst ratio, temperature, oxidant ratio and oxidant type were also investigated to find optimal reaction on benzyl alcohol oxidation for getting the highest conversion. (C) 2014 Elsevier B.V. All rights reserved.