Synthesis of a multifunctional alkoxysiloxane oligomer

Masashi Yoshikawa, Ryutaro Wakabayashi, Misa Tamai, Kazuyuki Kuroda

    Research output: Contribution to journalArticle

    9 Citations (Scopus)

    Abstract

    An alkoxysiloxane oligomer (1, SiMe[OSi(CHCH2)(OMe)2][OSi(CH2)3Cl(OMe)2]2), containing vinyl and chloropropyl groups, was synthesized as a precursor for sol-gel synthesis. Di-tert-butoxymethylhydroxysilane (t-BuO)2MeSiOH was reacted with (MeO)2(CH2CH)SiCl to form (t-BuO)2MeSiOSi(CHCH2)(OMe)2 which was further alkoxysilylated with Cl(CH2)3SiCl(OMe)2 to form 1. The 1H, 13C, 29Si NMR and HR-MS data confirmed the formation of 1, indicating the successful synthesis of an alkoxysiloxane oligomer possessing different kinds of functional groups by a chemoselective route. Hydrolysis of 1 under acidic conditions was completed in a few hours. The solution state 29Si NMR spectra of samples hydrolyzed and condensed at various reaction times show no signals due to species generated by the cleavage of the siloxane bonds in 1, indicating the validity of the synthesized substance as a precursor for the formation of hybrids with homogeneously distributed functional groups. Intramolecular condensation of 1 to form cyclic trisiloxane units proceeds more preferentially than intermolecular condensation.

    Original languageEnglish
    Pages (from-to)5362-5368
    Number of pages7
    JournalNew Journal of Chemistry
    Volume38
    Issue number11
    DOIs
    Publication statusPublished - 2014 Nov 1

    Fingerprint

    Oligomers
    Functional groups
    Condensation
    Nuclear magnetic resonance
    Siloxanes
    Sol-gels
    Hydrolysis

    ASJC Scopus subject areas

    • Chemistry(all)
    • Catalysis
    • Materials Chemistry

    Cite this

    Synthesis of a multifunctional alkoxysiloxane oligomer. / Yoshikawa, Masashi; Wakabayashi, Ryutaro; Tamai, Misa; Kuroda, Kazuyuki.

    In: New Journal of Chemistry, Vol. 38, No. 11, 01.11.2014, p. 5362-5368.

    Research output: Contribution to journalArticle

    Yoshikawa, M, Wakabayashi, R, Tamai, M & Kuroda, K 2014, 'Synthesis of a multifunctional alkoxysiloxane oligomer', New Journal of Chemistry, vol. 38, no. 11, pp. 5362-5368. https://doi.org/10.1039/c4nj00204k
    Yoshikawa, Masashi ; Wakabayashi, Ryutaro ; Tamai, Misa ; Kuroda, Kazuyuki. / Synthesis of a multifunctional alkoxysiloxane oligomer. In: New Journal of Chemistry. 2014 ; Vol. 38, No. 11. pp. 5362-5368.
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    abstract = "An alkoxysiloxane oligomer (1, SiMe[OSi(CHCH2)(OMe)2][OSi(CH2)3Cl(OMe)2]2), containing vinyl and chloropropyl groups, was synthesized as a precursor for sol-gel synthesis. Di-tert-butoxymethylhydroxysilane (t-BuO)2MeSiOH was reacted with (MeO)2(CH2CH)SiCl to form (t-BuO)2MeSiOSi(CHCH2)(OMe)2 which was further alkoxysilylated with Cl(CH2)3SiCl(OMe)2 to form 1. The 1H, 13C, 29Si NMR and HR-MS data confirmed the formation of 1, indicating the successful synthesis of an alkoxysiloxane oligomer possessing different kinds of functional groups by a chemoselective route. Hydrolysis of 1 under acidic conditions was completed in a few hours. The solution state 29Si NMR spectra of samples hydrolyzed and condensed at various reaction times show no signals due to species generated by the cleavage of the siloxane bonds in 1, indicating the validity of the synthesized substance as a precursor for the formation of hybrids with homogeneously distributed functional groups. Intramolecular condensation of 1 to form cyclic trisiloxane units proceeds more preferentially than intermolecular condensation.",
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