Syntheses and electrochromic and fluorescence properties of three double dithienylpyrroles derivatives

• Published in: Electrochimica acta Vol. 56; no. 18; pp. 6352 - 6360
• Main Authors: Wang, Gang, Fu, Xiangkai, Huang, Jing, Wu, Chuan Long, Wu, Liu, Deng, Jun, Du, Qiuliang, Zou, Xiaochuan
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 15.07.2011; Elsevier
• Subjects: Addition polymerization; Applied sciences; Aromatic diamines; Chemistry; Derivatives; Double dithienylpyrroles; Electrical, magnetic and optical properties; Electrochemistry; Electrochromic materials; Electrochromism; Electropolymerization; Energy gaps (solid state); Exact sciences and technology; Fluorescence; General and physical chemistry; Miscellaneous (electroosmosis, electrophoresis, electrochromism, electrocrystallization, ...); Organic polymers; Physicochemistry of polymers; Polymeric films; Properties and characterization; Scanning electron microscopy; Thermogravimetric analysis; Fluorescence; Aromatic diamines; Electrochromic materials; Electropolymerization; Double dithienylpyrroles; Pyrrole derivative copolymer; Thermogravimetry; Electrochromism; Thiophene copolymer; Electrochemical polymerization; Thermal stability; Diamine; Paal Knorr synthesis; Preparation; Aromatic compound; Thermal analysis; Electrochemical reaction; Spectroelectrochemistry
• ISSN: 0013-4686; 1873-3859
• DOI: 10.1016/j.electacta.2011.05.023

► Three kinds of double dithienylpyrroles derivatives have been successfully prepared by the Knorr–Paal condensation between 1,4-di(thiophen-2-yl) butane-1,4-dione and aromatic diamines. ► Their polymer films were successfully synthesized via electropolymerization. ► The polymer films had stable and well-defined reversible redox process, low optical band gap and multicolor electrochromic behavior. ► All the monomers and polymers exhibited different intensity emission bands at different wavelengths. Three double dithienylpyrroles derivatives have been successfully prepared by performing a Knorr–Paal condensation between 1,4-di(thiophen-2-yl) butane-1,4-dione and various aromatic diamines. Additionally, their corresponding polymer films were synthesized via electropolymerization. Their electrochemical, spectroelectrochemical and electrochromic behaviors were further investigated by thermogravimetric analysis, scanning electron microscopy, cyclic voltammetry, UV–vis absorption and fluorescence emission spectra. Scanning electron microscopy and thermogravimetric analysis demonstrated that the polymer films possessed homogeneous, compact and smooth layer structures and thermal stabilities (up to nearly 180°C). Cyclic voltammograms and UV–vis absorption spectra studies showed that the polymer films have stable, well-defined, reversible redox processes, low optical band gaps (Eg<2.2eV) and multicolor electrochromic behaviors. Additionally, the fluorescence spectra study showed that all of the monomers and polymers exhibited different intensity emission bands at different wavelengths.