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Please use this identifier to cite or link to this item: https://dspace.ffh.bg.ac.rs/handle/123456789/832
Title: Chemical oxidative polymerization of aminodiphenylamines
Authors: Ćirić-Marjanović, Gordana 
Trchová, Miroslava
Konyushenko, Elena N
Holler, Petr
Stejskal, Jaroslav
Issue Date: 12-Jun-2008
Journal: The journal of physical chemistry. B
Abstract: 
The course of oxidation of 4-aminodiphenylamine with ammonium peroxydisulfate in an acidic aqueous ethanol solution as well as the properties of the oxidation products were compared with those of 2-aminodiphenylamine. Semiconducting oligomers of 4-aminodiphenylamine and nonconducting oligomers of 2-aminodiphenylamine of weight-average molecular weights 3700 and 1900, respectively, were prepared by using an oxidant to monomer molar ratio of 1.25. When this ratio was changed from 0.5 to 2.5, the highest conductivity of oxidation products of 4-aminodiphenylamine, 2.5 x 10 (-4) S cm (-1), was reached at the molar ratio [oxidant]/[monomer] = 1.5. The mechanism of the oxidative polymerization of aminodiphenylamines has been theoretically studied by the AM1 and MNDO-PM3 semiempirical quantum chemical methods combined with the MM2 molecular mechanics force-field method and conductor-like screening model of solvation. Molecular orbital calculations revealed the prevalence of N prim-C10 coupling reaction of 4-aminodiphenylamine, while N prim-C5 is the main coupling mode between 2-aminodiphenylamine units. FTIR and Raman spectroscopic studies confirm the prevalent formation of linear N prim-C10 coupled oligomers of 4-aminodiphenylamine and suggest branching and formation of phenazine structural units in the oligomers of 2-aminodiphenylamine. The results are discussed with respect to the oxidation of aniline with ammonium peroxydisulfate, leading to polyaniline, in which 4-aminodiphenylamine is the major dimer and 2-aminodiphenylamine is the most important dimeric intermediate byproduct.
URI: https://dspace.ffh.bg.ac.rs/handle/123456789/832
ISSN: 1520-6106
DOI: 10.1021/jp710963e
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University of Belgrade
Faculty of Physical Chemistry
Studentski trg 12-16
11158 Belgrade 118
PAC 105305
SERBIA
University of Belgrade Faculty of Physical Chemistry