A new approach for synthesis of electroactive phenol based polymer: 4-(2,5-Di(thiophen-2-yl)-1H-pyrrol-1-yl)phenol and its oxidative polymer

In this study, the 4-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)phenol (4-DTPP) was synthesized by the reaction of 1,4-di(2-thienyl)-1,4-butanedione and 4-aminophenol. This monomer was electrochemically polymerized in the presence of LiClO4 as the supporting electrolyte in acetonitrile (AN). The copolymerization were achieved in the presence of thiophene (Th) with 3,4-ethylenedioxythiophene (EDOT) in 0.1 M LiClO4/AN electrolyte-solvent couple. The polymer of 4-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)phenol was synthesized by oxidative polycondensation reaction in an aqueous alkaline medium using NaOCl (30%) as oxidant. The structures of compounds were confirmed by FT-IR, UV–vis, and 1H-NMR techniques. The characterizations of compounds were made by TG–DTA, DSC, gel permeation chromatography (GPC) and solubility tests. Electrical conductivities of the synthesized monomer and polymer were measured by four-point probe technique using a Keithley 2400 electrometer. Fluorescence measurements were carried out in various solvents.

The electroactive materials from polyphenol substituted were synthesized by oxidative polymerization and examined by cyclic voltammetry, GPC, FT-IR, NMR, spectrofluorometry, optical and electrical measurements. The synthesized materials were separately electrocopolymerized with thiophene and 3,4-ethylenedioxythiophene. The electrical conductivities highly increased by exposure to iodine vapour. So, polymer has higher conductivity than monomer. Also, monomer has quite high fluorescent intensity value. Therefore, it is a good candidate in use of ion-selective sensor. The synthesized oxidative polymer can be also used in aerospace applications with its fine thermal stability.Figure optionsDownload as PowerPoint slideHighlights
► Novel a polymer containing thiophene groups in the side chain was synthesized through oxidative polymerization of 4-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)phenol.
► At the same time, copolymers of the monomer and polymer were synthesized at electrochemically.
► The all copolymers were obtained on ITO glass plates and they are solved in electropolymerization media.
► The optical band gap values of monomer and polymer were theoretically calculated and important results were obtained.
► Also, the thermal and fluorescence characteristics of the synthesized monomer and polymer were investigated and important data were recorded.
► Conductivity value of the polymer was found to be higher than monomer.