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Effects of Phenyl‐ and Methyl‐Substituents on p ‐Phenylenediamine, an Electrochemical and Spectral Study
Author(s) -
Chung YiChun,
Su Yuhlong Oliver
Publication year - 2009
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200900074
Subject(s) - chemistry , substituent , electrochemistry , redox , radical , spectral properties , medicinal chemistry , absorption spectroscopy , cyclic voltammetry , electron transfer , absorption (acoustics) , photochemistry , computational chemistry , organic chemistry , electrode , quantum mechanics , acoustics , physics
Two series of substituted p ‐phenylenediamines have been studied for their electronic effects on redox potential and spectral properties. p ‐Phenylenediamines and N,N,N′,N” ‐tetramethyl‐ p ‐phenylenediamine substituted with different numbers of phenyl groups have been synthesized and their cyclic voltammograms have been obtained. The correlation between the substituent number and the redox potential appears linear. The slope reflects the additive effect of electron‐donating methyl and electron‐withdrawing phenyl groups. The absorption spectra of the cation radicals indicate that phenyl‐substituted ones have broad intervalence‐charge transfer bands. The p ‐phenylenediamines exhibit different properties from triphenylamines in that the oxidized forms are more stable in CH 3 CN then those in CH 2 Cl 2 . Some of the cation radicals or dications could undergo follow‐up chemical reactions and form products that are more easily oxidized.