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Role of p-benzoquinone in the synthesis of a conducting polymer, polyaniline

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    SYSNO ASEP0504103
    Document TypeJ - Journal Article
    R&D Document TypeJournal Article
    Subsidiary JČlánek ve WOS
    TitleRole of p-benzoquinone in the synthesis of a conducting polymer, polyaniline
    Author(s) Bláha, Michal (UMCH-V) RID
    Marek, F. (CZ)
    Morávková, Zuzana (UMCH-V) RID, ORCID
    Svoboda, Jan (UMCH-V) ORCID, RID
    Brus, Jiří (UMCH-V) RID, ORCID
    Dybal, Jiří (UMCH-V) RID, ORCID
    Prokeš, J. (CZ)
    Varga, M. (CZ)
    Stejskal, Jaroslav (UMCH-V) RID, ORCID, SAI
    Source TitleACS Omega. - : American Chemical Society - ISSN 2470-1343
    Roč. 4, č. 4 (2019), s. 7128-7139
    Number of pages12 s.
    Languageeng - English
    CountryUS - United States
    Keywordsp-benzoquinone ; 2,5-dianilino-p-benzoquinone ; conducting polymers
    Subject RIVCD - Macromolecular Chemistry
    OECD categoryPolymer science
    R&D ProjectsGA18-12925S GA ČR - Czech Science Foundation (CSF)
    Method of publishingOpen access
    Institutional supportUMCH-V - RVO:61389013
    UT WOS000466552500116
    EID SCOPUS85064803105
    DOI10.1021/acsomega.9b00542
    AnnotationPolyaniline (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.
    WorkplaceInstitute of Macromolecular Chemistry
    ContactEva Čechová, cechova@imc.cas.cz ; Tel.: 296 809 358
    Year of Publishing2020
    Electronic addresshttps://pubs.acs.org/doi/pdf/10.1021/acsomega.9b00542
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