Electrochemical characterization of small organic hole-transport molecules based on the triphenylamine unit |
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| Institution: | 1. College of Civil Engineering & Architecture, Qingdao Agricultural University, Qingdao 266109, China;2. Dsign and Research Institute of Marine & Offshore, Qingdao Beihai Shipbuilding Heavy Industry Co., LTD, Qingdao, 266520, China;3. The 2nd Engineering Co.Ltd of China Railway 17 Bureau Group Corporation, Xi’an 710043, China;1. School of Chemistry and Chemical Engineering, Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, Hefei University of Technology, Hefei, 230009, PR China;2. Key Laboratory of Photovoltaic and Energy Conservation Materials, Institute of Applied Technology, Hefei Institutes of Physical Science, Chinese Academy of Sciences, Hefei, 230088, PR China;3. Computational Chemistry Laboratory, Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, 5166616471, Iran;1. Key Laboratory of High Performance Plastics (Jilin University), Ministry of Education, National & Local Joint Engineering Laboratory for Synthesis Technology of High Performance Polymer, Jilin University, Qianjin Street 2699, Changchun 130012, PR China;2. School of Materials Science and Engineering, Changchun University of Technology, Changchun 130012, PR China;3. Department of Materials Science and Engineering, National University of Singapore, Singapore 117574, Singapore;1. Department of Polymer Chemistry and Technology, Faculty of Chemical Technology, Kaunas University of Technology, K. Barsausko St. 59-500, Kaunas, Lithuania;2. Belarusian State University, 4, Nezavisimosti Avenue, 220030, Minsk, Belarus;3. Computer, Electrical and Mathematical Science and Engineering Division, 4700 King Abdullah University of Science and Technology, Thuwal, 23955-6900, Saudi Arabia;4. Department of Experimental Physics, Taras Shevchenko National University of Kyiv, Hlushkova Avenue, 4, 03127, Kyiv, Ukraine |
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| Abstract: | A series of substituted triphenylamine-containing organic compounds are synthesized and their hole-transport properties are examined by electrochemical and spectroelectrochemical methods. Several substituted tirphenylamines exhibited irreversible electron-transfer reactions both in the oxidative and reductive scan. On the other hand, the cyclic voltammograms of the p-phenylenediamine series are well defined. N,N′-bis(4-nitrophenyl)-N,N′-diphenyl-1,4-phenylenediamine (NPD) exhibited two reversible oxidation redox couples at +1.00 and +1.28 V vs. Ag/AgCl in dichloromethane solution. There is one reversible reduction redox couple at −1.12 V and one irreversible wave with Ep,c at −1.87 V. Cyano-substituted p-phenylenediamine (CPD) exhibited similar oxidation redox couples. Amino-substituted p-phenylenediamine (APD) is easier to oxidize than NPD and CPD. APD exhibits two reversible oxidation redox couples at +0.40 and +0.70 V and two extra irreversible oxidation waves at +1.26 and +1.52 V. Optically transparent thin-layer electrode (OTTLE) coupled with UV/Vis/NIR spectroscopy was used to examine the oxidation products of the above reactions. The electrogenerated cation and dication of the substituted p-phenylenediamine are very stable in the spectroelectrochemical studies. Oxidation of the compound APD exhibited a distinguished absorption pattern, which is different from those of compound NPD and compound CPD. |
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