Novel trends of electrochemical oxidation of amino-substituted triphenylamine derivatives

A series of amino-substituted triphenylamine derivatives have been synthesized and the electrochemical and spectral characteristics has been investigated. Triphenylamine is also used as a reference. p-Amino-triphenylamine ( 1 ) showed two reversible redox couples at E 1/2 = 0.59 and 1.09 V in CH 2Cl...

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Bibliographic Details
Published in:	Journal of electroanalytical chemistry (Lausanne, Switzerland) Vol. 575; no. 1; pp. 95 - 101
Main Authors:	Yuan Chiu, Kuo, Xiang Su, Tsi, Hong Li, Jia, Lin, Tsung-Hsien, Liou, Guey-Sheng, Cheng, Shu-Hua
Format:	Journal Article
Language:	English
Published:	Amsterdam Elsevier B.V 01-01-2005 Elsevier Science
Subjects:	Amino-substituted triphenylamine Cation radicals Chemistry Dication Electrochemical oxidation Electrochemistry Exact sciences and technology General and physical chemistry Kinetics and mechanism of reactions Spectroelectrochemistry Cation radicals Dication Spectroelectrochemistry Amino-substituted triphenylamine Electrochemical oxidation Reaction intermediate Electron transfer Experimental study Half wave potential Cyclic voltammetry Electrochemical properties Oxidative degradation Tertiary amine Redox potential Electrochemical reaction Organic radical cation Ultraviolet visible spectrometry
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Summary:	A series of amino-substituted triphenylamine derivatives have been synthesized and the electrochemical and spectral characteristics has been investigated. Triphenylamine is also used as a reference. p-Amino-triphenylamine ( 1 ) showed two reversible redox couples at E 1/2 = 0.59 and 1.09 V in CH 2Cl 2. The stable cation radical 1 + was generated electrochemically and exhibited strong bands in the visible region as determined in situ by UV/Vis/NIR spectroelectrochemical methods. The second oxidation product 1 2+ could be generated electrochemically, but was not very stable after long time electrolysis at applied potentials higher than 1.15 V. p, p′-Diamino-triphenylamine ( 2 ), p-methyl- p′, p″-diamino-triphenylamine ( 2a ), p-methoxy- p′, p″-diamino-triphenylamine ( 2 b ) and p, p′, p″-triamino-triphenylamine ( 3 ) are more stable in CH 3CN than in CH 2Cl 2 during cyclic scans at oxidation potentials. The oxidation potentials of the various amino-substituted TPA derivatives and the stability of the oxidized products are solvent-dependent and relate to the molecular structures.
ISSN:	1572-6657 1873-2569
DOI:	10.1016/j.jelechem.2004.09.005