A comparative study of electrochemical, optical properties and electropolymerization behavior of thiophene- and furan-su
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Henry J. Spratt Central Analytical Research Facility, Institute for Future Environments, Queensland University of Technology (QUT), Brisbane 4001, Australia
Sergei Manzhos Department of Mechanical Engineering, Faculty of Engineering, National University of Singapore Block EA #07-08, Singapore 117576, Singapore
Anthony P. O’Mullane, Godwin A. Ayoko, and Prashant Sonarb) School of Chemistry, Physics and Mechanical Engineering, Nanotechnology and Molecular Sciences Discipline, Queensland University of Technology (QUT), Brisbane 4001, Australia (Received 22 August 2016; accepted 10 January 2017)
Electropolymerization is a promising approach to produce thin films of active organic conjugated materials on a desired conducting substrate. In this work, an electropolymerization study has been carried out on two diketopyrrolopyrrole (DPP)-based monomers 2,5-bis(2-butyloctyl)-3,6-di (furan-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (BO-DPPF) and 2,5-bis(2-butyloctyl)-3,6-di (thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (BO-DPPT). These monomers consist of thiophene and furan heterocyclic moieties attached to a DPP core with a common solubilizing alkyl chain (butyl-octyl). The properties of these monomers were analyzed via differential scanning calorimetry, thermogravimetric analysis, UV–Vis spectrometry (UV) and photoluminescence. Cyclic voltammetry (CV) studies indicate the presence of irreversible oxidation and reduction reactions. The electropolymerization of BO-DPPF and BO-DPPT electron-deficient monomers to form polymer films on a glassy carbon electrode is achieved by applying a potential between 2 V and 2 V versus ferrocene for up to 50 cycles. The properties of the polymers were investigated using the cyclic voltammetry (CV) technique.
I. INTRODUCTION
The chemical synthesis of fused aromatic diketopyrrolopyrrole (DPP) core pigments was reported by Ciba Specialty chemicals a few decades back.1 DPP is an aromatic conjugated planar moiety with lactam nitrogen and two electron-withdrawing carbonyl groups, which makes DPP a promising solution-processable block for synthesizing many varieties of donor–acceptor (D–A)based polymers.2 Recently, DPP-based semiconducting polymers have become a popular choice of material for organic thin film transistors and organic photovoltaic devices.3,4 Worldwide, many groups are exploring Contributing Editor: Erik G. Herbert Address all correspondence to these authors. a) e-mail: [email protected] b) e-mail: [email protected] c) Current Address: Future Industries Institute, University of South Australia, Adelaide, Australia DOI: 10.1557/jmr.2017.26
structure–property relationships of such materials.5 These DPP-based organic semiconductors not only exhibit exceptional thermal and mechanical robustness but also superior photochemical stability. Such features are required for fabricating stable organic electronic devices. Small molecules of DPP have been widely used for organic photovoltaic applications because of their excellent light absorbing and charge transportin
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