Polymerization of cyclohexanone formaldehyde resin modified with carbazole‐9‐carbonyl chloride

Abstract

Purpose

The purpose of this paper is to synthesise cyclohexanone formaldehyde resin (CFR)‐modified carbazole‐9‐carbonyl chloride (CzCl) via hydroxyl groups of CFR. This carbazole‐modified resin (Cz‐CFR) comonomer was characterised by common techniques such as UV, NMR, FTIR, fluorescence spectrophotometer, and scanning electron microscopy. The oxidative and electrochemical polymerisation of CzCl‐modified cyclohexanone formaldehyde resin (Cz‐CFR) were carried out.

Design/methodology/approach

Cz‐CFR comonomer was synthesised by the esterification reaction of CzCl and hydroxyl groups of CFR. Then, for the chemical polymerisation, ceric ammonium nitrate (CAN)/DMF solution was added to the comonomer/DMF solution. The precipitate was filtered, washed with chloroform and dried. For the electrochemical polymerisation, potentiodynamic electrodeposition of Cz‐CFR comonomer in dichloromethane on to Pt was carried out.

Findings

The concentration effect of CAN and Cz‐CFR on the conductivity, yield, solubility and T_g values of the polymers (P(Cz‐CFR)) were investigated. Spectrophotometric (UV‐visible, NMR), and cyclovoltammetric, polarisation curves, solid‐state conductivity and in situ spectroelectrochemical measurements were performed for the characterisation of homopolymer (polycarbazole (PCz)) and P (Cz‐CFR) films comparatively. The ionisation potentials (I_p), electron affinity (E_a), optical band gap (E_g), peak potentials (E_p), doping degree (y), and specific capacitance (C_sp), of polymer films were calculated from the results of polarisation curves, cyclovoltammetry and electrochemical impedance spectroscopy.

Research limitations/implications

This paper focuses on obtaining a conductive polymer by using a fluorescence comonomer, which is an insulator.

Practical implications

This work provides technical information for the synthesis of fluorescence comonomer and conducting an alternative polymer.

Originality/value

The paper describes how a new Cz‐CFR comonomer was synthesised. This comonomer has a higher T_g value than CFR alone and also has fluorescence property. Cz‐CFR was polymerised by ceric salt and by electrochemical polymerisation. The band gap of the copolymer is not remarkably lower than polycarbazole.

Citation

Kızılcan, N., Hocaoğlu, B. and Ustamehmetoğlu, B. (2011), "Polymerization of cyclohexanone formaldehyde resin modified with carbazole‐9‐carbonyl chloride", Pigment & Resin Technology, Vol. 40 No. 3, pp. 143-153. https://doi.org/10.1108/03699421111130405