Poly(pyrrole) films efficiently electrodeposited using new monomers derived from 3-bromopropyl-N-pyrrol and dihydroxyacetophenone—Electrocatalytic reduction ability towards bromocyclopentane

Three monomers 6-[3′-N-pyrrolpropoxy]-2-hydroxyacetophenone (1), 5-(3′-N-pyrrol propoxy)-2-hydroxyacetophenone (2) and 4-(3′-N-pyrrolpropoxy)-2-hydroxyacetophenone (3) were synthesized and their poly(pyrrole) films were electrodeposited on glassy carbon (GC) and Indium tin oxide (ITO) conductive electrodes by anodic oxidation in acetonitrile solutions containing n-Bu)4N+ClO4− (TBAP 0.1 M). These films, currently called modified electrodes (noted ME), were obtained by the successive cycling at the appropriate potentials. These films contain chelating sites such as carbonyl group bearing the phenolic function which could play an important role in coordination chemistry. The electrodeposited poly(pyrrole) films on the ITO conductive glass electrodes offer some analytical advantages as the optical and electronic properties. Consequently, these new materials of electrodes were characterized by cyclic voltammetry while the morphology of these films was studied by FT-IR spectroscopy, scanning electron microscopy (SEM), dispersive energy X-ray spectroscopy and atomic force microscopy (AFM). The AFM studies show that the morphology of polypyrrole (PPy) films, electrodeposited on ITO surface, depends on the specific structure of the compound deriving from the monoalkylated dihydroxyacetophenone 1, 2 and 3. The coordination of copper was performed by electroreduction reaction in presence of ligand (3) and copper acetate salt. The resulting electrode material was tested towards the electrocatalytic activity in the reduction of bromocyclopentane.