The synthesis and electrochemical behaviour of carbazole-substituted phthalocyanines

Abstract

The syntheses of new cobalt and zinc phthalocyanine complexes containing carbazole (Cz) substituents at the peripheral positions are reported (CzCoPc and CzZnPc). The reaction of Cz with 4-iodophthalonitrile in the presence of a catalytic amount of copper(I) oxide and potassium carbonate led to the formation of 4-(9H-carbazol-9-yl) phthalonitrile. Furthermore, by heating the dinitrile and anhydrous metal salts (CoCl2, Zn(CH3COO)2) at 160 °C in n-hexanol in the presence of DBU, the phthalocyanines were obtained. They were characterised by 1H NMR, FT-IR, UV-Vis and MS spectroscopic data. Aggregation behaviours of Pcs were investigated in THF. Electrochemical redox behaviour of CzCoPc was investigated by cyclic voltammetry depending on the potential range, and the oxidation and reduction products were followed by UV-Visible absorption measurements. Polymerisation of CzCoPc was carried out by potentiodynamic methods on glassy carbon electrode, and the catalytic activity of resulting polymer (P[CzCoPc]) was tested comparatively with polycarbazole (PCz)-coated electrode for dopamine and better response was obtained for P[CzCoPc] modified electrode.