Synthesis and Properties of Fully Triphenylamine-based Polyamides Bearing 3,5-bis(Trifluoromethyl) and/or 3,5-dimethyl Substituents on the Pendent Phenyl Units |
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Authors: | Sheng-Huei Hsiao Chien-Nan Wu |
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Affiliation: | 1. Department of Chemical Engineering and Biotechnology, National Taipei University of Technology, Taipei, Taiwan;2. Department of Chemical Engineering, Tatung University, Taipei, Taiwan |
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Abstract: | Four new fully triphenylamine-based polyamides coded as polyamide (CF3,CF3), polyamide (CF3,CH3), polyamide (CH3,CF3), and polyamide (CH3,CH3) were synthesized by the phosphorylation polyamidation reaction from various combinations of 3,5-bis(trifluoromethyl)-4′,4″-dicarboxytriphenylamine, 3,5-dimethyl-4′,4″-dicarboxytriphenylamine, 3,5-bis(trifluoromethyl)-4′,4″-diaminotriphenylamine, and 3,5-dimethyl-4′,4″-diaminotriphenylamine. All the polyamides were amorphous and readily soluble in many common organic solvents and could be solution-cast into transparent, flexible, and strong films with good mechanical properties. They had useful levels of thermal stability associated with high glass-transition temperatures of 268–287°C and 10?wt%-loss temperatures in excess of 500°C. Cyclic voltammograms of the film of polyamide (CH3,CH3) on the indium-tin oxide-coated glass substrates exhibited two oxidation redox couples with E1/2 around 0.82 and 1.29?V vs. Ag/AgCl in tetrabutylammonium perchlorate/acetonitrile solution, accompanied by a color change from pale yellow neutral state to dark green oxidized state. The CF3-substituted polyamides displayed a higher oxidation potential and less electrochemical stability as compared to the CH3-substituted analogues. |
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Keywords: | Electrochemistry electrochromism polyamides redox-active polymers trifluoromethyl triphenylamine |
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