Palladium-catalyzed synthesis of oligo(methylthio) aniline and conversion to polyacene-type electrolytes bearing phenothiazinium repeating units

Kenichi Oyaizu, Fumio Mitsuhashi, Eishun Tsuchida

    研究成果: Article

    14 引用 (Scopus)

    抄録

    The synthetic routes to ladder polymers which consist of benzenetetrayl subunits with imino and methyl-sulfonio linkages are described. As the key intermediate, oligo- and polyaniline derivatives having pendant methylthio groups are prepared by the Pd-catalyzed aryl amination from various monomers. The Oxidation of the polymers with H2O2 in the presence of CH3COOH effects the high yielding conversion of methylthio to methylsulfinyl groups without the formation of the undesired methylsulfonyl groups. The superacid-induced condensation of the resulting polymers under dilution conditions induced the polymer-analogous intramolecular electrophilic ring closure reaction of the hydroxy(methyl)(phenyl)sulfonium cation onto the adjacent benzene ring to yield the required ladder polymers which have proved to be semiconductors with intrinsic electric conductivities of ca. 10-5 S · cm-1.

    元の言語English
    ページ(範囲)1328-1336
    ページ数9
    ジャーナルMacromolecular Chemistry and Physics
    203
    発行部数10-11
    DOI
    出版物ステータスPublished - 2002 7 29

    Fingerprint

    Bearings (structural)
    Palladium
    Aniline
    aniline
    Electrolytes
    palladium
    Polymers
    electrolytes
    polymers
    synthesis
    Ladders
    ladders
    Amination
    rings
    Polyaniline
    Benzene
    linkages
    Dilution
    closures
    dilution

    ASJC Scopus subject areas

    • Polymers and Plastics
    • Materials Chemistry
    • Organic Chemistry
    • Physical and Theoretical Chemistry

    これを引用

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    title = "Palladium-catalyzed synthesis of oligo(methylthio) aniline and conversion to polyacene-type electrolytes bearing phenothiazinium repeating units",
    abstract = "The synthetic routes to ladder polymers which consist of benzenetetrayl subunits with imino and methyl-sulfonio linkages are described. As the key intermediate, oligo- and polyaniline derivatives having pendant methylthio groups are prepared by the Pd-catalyzed aryl amination from various monomers. The Oxidation of the polymers with H2O2 in the presence of CH3COOH effects the high yielding conversion of methylthio to methylsulfinyl groups without the formation of the undesired methylsulfonyl groups. The superacid-induced condensation of the resulting polymers under dilution conditions induced the polymer-analogous intramolecular electrophilic ring closure reaction of the hydroxy(methyl)(phenyl)sulfonium cation onto the adjacent benzene ring to yield the required ladder polymers which have proved to be semiconductors with intrinsic electric conductivities of ca. 10-5 S · cm-1.",
    keywords = "Charge transfer, Conjugated polymers, Heteroatom-containing polymers, Polycondensation, Polyelectrolytes",
    author = "Kenichi Oyaizu and Fumio Mitsuhashi and Eishun Tsuchida",
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    T1 - Palladium-catalyzed synthesis of oligo(methylthio) aniline and conversion to polyacene-type electrolytes bearing phenothiazinium repeating units

    AU - Oyaizu, Kenichi

    AU - Mitsuhashi, Fumio

    AU - Tsuchida, Eishun

    PY - 2002/7/29

    Y1 - 2002/7/29

    N2 - The synthetic routes to ladder polymers which consist of benzenetetrayl subunits with imino and methyl-sulfonio linkages are described. As the key intermediate, oligo- and polyaniline derivatives having pendant methylthio groups are prepared by the Pd-catalyzed aryl amination from various monomers. The Oxidation of the polymers with H2O2 in the presence of CH3COOH effects the high yielding conversion of methylthio to methylsulfinyl groups without the formation of the undesired methylsulfonyl groups. The superacid-induced condensation of the resulting polymers under dilution conditions induced the polymer-analogous intramolecular electrophilic ring closure reaction of the hydroxy(methyl)(phenyl)sulfonium cation onto the adjacent benzene ring to yield the required ladder polymers which have proved to be semiconductors with intrinsic electric conductivities of ca. 10-5 S · cm-1.

    AB - The synthetic routes to ladder polymers which consist of benzenetetrayl subunits with imino and methyl-sulfonio linkages are described. As the key intermediate, oligo- and polyaniline derivatives having pendant methylthio groups are prepared by the Pd-catalyzed aryl amination from various monomers. The Oxidation of the polymers with H2O2 in the presence of CH3COOH effects the high yielding conversion of methylthio to methylsulfinyl groups without the formation of the undesired methylsulfonyl groups. The superacid-induced condensation of the resulting polymers under dilution conditions induced the polymer-analogous intramolecular electrophilic ring closure reaction of the hydroxy(methyl)(phenyl)sulfonium cation onto the adjacent benzene ring to yield the required ladder polymers which have proved to be semiconductors with intrinsic electric conductivities of ca. 10-5 S · cm-1.

    KW - Charge transfer

    KW - Conjugated polymers

    KW - Heteroatom-containing polymers

    KW - Polycondensation

    KW - Polyelectrolytes

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    M3 - Article

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    JO - Macromolecular Chemistry and Physics

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