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Role of p-Benzoquinone in the Synthesis of a Conducting Polymer, Polyaniline

[Image: see text] Polyaniline (PANI) and 2,5-dianilino-p-benzoquinone both are formed by oxidation of aniline in an acidic aqueous environment. The aim of this study is to understand the impact of addition of p-benzoquinone on the structure of PANI prepared by the oxidation of aniline hydrochloride...

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Autores principales: Bláha, Michal, Marek, Filip, Morávková, Zuzana, Svoboda, Jan, Brus, Jiří, Dybal, Jiří, Prokeš, Jan, Varga, Martin, Stejskal, Jaroslav
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648476/
https://www.ncbi.nlm.nih.gov/pubmed/31459822
http://dx.doi.org/10.1021/acsomega.9b00542
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author Bláha, Michal
Marek, Filip
Morávková, Zuzana
Svoboda, Jan
Brus, Jiří
Dybal, Jiří
Prokeš, Jan
Varga, Martin
Stejskal, Jaroslav
author_facet Bláha, Michal
Marek, Filip
Morávková, Zuzana
Svoboda, Jan
Brus, Jiří
Dybal, Jiří
Prokeš, Jan
Varga, Martin
Stejskal, Jaroslav
author_sort Bláha, Michal
collection PubMed
description [Image: see text] Polyaniline (PANI) and 2,5-dianilino-p-benzoquinone both are formed by oxidation of aniline in an acidic aqueous environment. The aim of this study is to understand the impact of addition of p-benzoquinone on the structure of PANI prepared by the oxidation of aniline hydrochloride with ammonium peroxydisulfate and to elucidate the formation of low-molecular-weight byproducts. An increasing yield and size-exclusion chromatography, Fourier-transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy, and nuclear magnetic resonance analyses of the products show that p-benzoquinone does not act as a terminating agent in the synthesis of PANI and the content of 2,5-dianilino-p-benzoquinone increases with the increasing molar concentration of p-benzoquinone in the reaction mixture, [BzQ]. Regarding the structure of PANI, Raman and UV–visible spectra show that the doping level and the charge delocalization both decrease with the increase of [BzQ], and the FTIR spectra of the PANI bases indicate an increased concentration of benzenoid units at higher [BzQ]. We explain these observations by an increasing concentration of structural defects in PANI chains and propose a 2,5-dianilino-p-benzoquinone-like structure of these defects present as pendant groups. The bands typical of 2,5-dianilino-p-benzoquinone-like moiety are observed even in the vibrational spectra of the sample prepared without addition of p-benzoquinone. This confirms in situ oxidation of aniline to p-benzoquinone within the course of the oxidation of aniline hydrochloride to PANI.
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spelling pubmed-66484762019-08-27 Role of p-Benzoquinone in the Synthesis of a Conducting Polymer, Polyaniline Bláha, Michal Marek, Filip Morávková, Zuzana Svoboda, Jan Brus, Jiří Dybal, Jiří Prokeš, Jan Varga, Martin Stejskal, Jaroslav ACS Omega [Image: see text] Polyaniline (PANI) and 2,5-dianilino-p-benzoquinone both are formed by oxidation of aniline in an acidic aqueous environment. The aim of this study is to understand the impact of addition of p-benzoquinone on the structure of PANI prepared by the oxidation of aniline hydrochloride with ammonium peroxydisulfate and to elucidate the formation of low-molecular-weight byproducts. An increasing yield and size-exclusion chromatography, Fourier-transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy, and nuclear magnetic resonance analyses of the products show that p-benzoquinone does not act as a terminating agent in the synthesis of PANI and the content of 2,5-dianilino-p-benzoquinone increases with the increasing molar concentration of p-benzoquinone in the reaction mixture, [BzQ]. Regarding the structure of PANI, Raman and UV–visible spectra show that the doping level and the charge delocalization both decrease with the increase of [BzQ], and the FTIR spectra of the PANI bases indicate an increased concentration of benzenoid units at higher [BzQ]. We explain these observations by an increasing concentration of structural defects in PANI chains and propose a 2,5-dianilino-p-benzoquinone-like structure of these defects present as pendant groups. The bands typical of 2,5-dianilino-p-benzoquinone-like moiety are observed even in the vibrational spectra of the sample prepared without addition of p-benzoquinone. This confirms in situ oxidation of aniline to p-benzoquinone within the course of the oxidation of aniline hydrochloride to PANI. American Chemical Society 2019-04-19 /pmc/articles/PMC6648476/ /pubmed/31459822 http://dx.doi.org/10.1021/acsomega.9b00542 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Bláha, Michal
Marek, Filip
Morávková, Zuzana
Svoboda, Jan
Brus, Jiří
Dybal, Jiří
Prokeš, Jan
Varga, Martin
Stejskal, Jaroslav
Role of p-Benzoquinone in the Synthesis of a Conducting Polymer, Polyaniline
title Role of p-Benzoquinone in the Synthesis of a Conducting Polymer, Polyaniline
title_full Role of p-Benzoquinone in the Synthesis of a Conducting Polymer, Polyaniline
title_fullStr Role of p-Benzoquinone in the Synthesis of a Conducting Polymer, Polyaniline
title_full_unstemmed Role of p-Benzoquinone in the Synthesis of a Conducting Polymer, Polyaniline
title_short Role of p-Benzoquinone in the Synthesis of a Conducting Polymer, Polyaniline
title_sort role of p-benzoquinone in the synthesis of a conducting polymer, polyaniline
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648476/
https://www.ncbi.nlm.nih.gov/pubmed/31459822
http://dx.doi.org/10.1021/acsomega.9b00542
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