Synthesis and electrochemical properties of new metal-free and metallophthalocyanines bearing 2,6-dimethylquinoline-4-yl derivatives

4-[(2,6-Dimethylquinoline-4-yl)oxy] peripherally substituted metal free (4), cobalt(II) (5), copper(II) (6) and manganese(III) (7) phthalocyanines were synthesized by using phthalonitrile derivative (3). The synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, UV-Vis, elemental analysis and mass spectroscopy. Redox properties of H2Pc (4), CoPc (5), CuPc (6) and MnPc (7) were investigated via cyclic (CV) and square wave voltammetry (SWV) in DCM/TBAP electrolyte on a Pt working electrode. While (CoPc)-Pc-II gave a metal-based reduction process in addition to the ring-based reduction process, (MnClPc)-Cl-III gave only metal based reduction reactions and H2Pc, CuPc gave only Pc based reduction reactions, as expected. (C) 2017 Elsevier Ltd. All rights reserved.