Synthesis of disulfide-containing aniline and copolymerization with aniline

Jun Sang Cho, Saya Sato, Shinji Takeoka, Eishun Tsuchida

    Research output: Contribution to journalArticle

    38 Citations (Scopus)

    Abstract

    A novel disulfide-containing aniline, 1,4-dihydrobenzo[d][1,2] dithiin-5-ylamin (1), was synthesized by the alkylbromination of 1,2-dimethyl-3-nitrobenzene, followed by the formation of a disulfide bond via thioesterification and then the reduction of the nitro group. The monomer showed a reductive and oxidative potential of the disulfide bond at -0.63 and 1.25 V (vs Ag/Ag+), respectively. Although the monomer showed the oxidative potential of aniline at 0.85 V (vs SCE), the electro- or chemical-oxidative polymerization of the monomer resulted in the formation of only the oligomer, suggesting that the disulfidecontaining condensed ring would prevent further propagation of the polymerization due to steric hindrance. However, the nearly ideal copolymerization of 1 with aniline (An) was carried out by chemical oxidative polymerization. The resulting copolymers (1/An = 1/1 and 2/1, by mole) had weight-averaged molecular weights (M̄w) of 10 000 and 6600, respectively, and good redox activities coupled with those of the polyaniline and disulfide group. The copolymer showed conductivities of 5.1 × 10-2 S/cm for 1/1 and 1.3 × 10-2 S/cm for 2/1 after being redoped with camphorsulfonic acid. It is suggested that these copolymers might be good candidates for the cathode materials of secondary polymer batteries.

    Original languageEnglish
    Pages (from-to)2751-2756
    Number of pages6
    JournalMacromolecules
    Volume34
    Issue number9
    DOIs
    Publication statusPublished - 2001 Apr 24

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    Aniline
    Disulfides
    Copolymerization
    Copolymers
    Monomers
    Polymerization
    Nitrobenzene
    Polyaniline
    Oligomers
    Polymers
    Cathodes
    Molecular weight
    Acids
    aniline

    ASJC Scopus subject areas

    • Materials Chemistry

    Cite this

    Synthesis of disulfide-containing aniline and copolymerization with aniline. / Cho, Jun Sang; Sato, Saya; Takeoka, Shinji; Tsuchida, Eishun.

    In: Macromolecules, Vol. 34, No. 9, 24.04.2001, p. 2751-2756.

    Research output: Contribution to journalArticle

    Cho, Jun Sang ; Sato, Saya ; Takeoka, Shinji ; Tsuchida, Eishun. / Synthesis of disulfide-containing aniline and copolymerization with aniline. In: Macromolecules. 2001 ; Vol. 34, No. 9. pp. 2751-2756.
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