Synthesis, electrochemistry and In situ spectroelectrochemistry of novel tetra dimethyl 5-oxyisophthalate substituted Co(II), Mn(III), and μ-oxo-dimer Fe(III) phthalocyanines

•Novel alpha and beta substituted μ-oxo-dimer iron phthalocyanines were synthesized.•Redox properties were investigated by voltammetry and spectroelectrochemistry.•Electrochemical measurements provided support for the μ-oxo-dimer structure.•The effect of ester-based substituents on the redox potentials were identified.

In this study, peripheral and non-peripheral tetra dimethyl 5-oxyisophthalate substituted cobalt(II), manganese(III) and μ-oxo-dimer Fe(III) phthalocyanines were synthesized by the reaction of dimethyl 5-hydroxyisophthalate with 1,2-dicyano-4-nitrobenzene/1,2-dicyano-3-nitrobenzen in dry N,N-dimethylformamide in the presence of anhydrous potassium carbonate. All purified phthalocyanine compounds were characterized by using FT-IR, UV–visible, MALDI-TOF mass spectrometry and elemental analyses results. Electron transfer properties of all novel cobalt(II), manganese(III) and μ-oxo-dimer Fe(III)phthalocyanine complexes were investigated by voltammetric and in situ spectroelectrochemical measurements in nonaqueous solution medium. Complexes were observed to display both metal-based and phthalocyanine ring-based reduction and oxidation electron transfer processes.

Graphical abstractNovel peripheral and non-peripheral tetra dimethyl 5-oxyisophthalate substituted cobalt(II), manganese(III), and μ-oxo-dimer Fe(III) phthalocyanines were synthesized by the reaction of dimethyl 5-hydroxyisophthalate with 1,2-dicyano-4-nitrobenzene/1,2-dicyano-3-nitrobenzen in dry N,N-dimethylformamide in the presence of anhydrous potassium carbonate. Electron transfer properties of the compounds were investigated by voltammetric and in situ spectroelectrochemical measurements in nonaqueous solution medium.Figure optionsDownload full-size imageDownload as PowerPoint slide