Use of N-Methyliminodiacetic Acid Boronate Esters in Suzuki-Miyaura Cross-Coupling Polymerizations of Triarylamine and Fluorene Monomers

Andrew Foster, Viktor Bagutski, Josue Ayuso Carrillo, Martin Humphries, Michael Ingleson, Michael Turner

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Polytriarylamine copolymers can be prepared by
    Suzuki-Miyaura cross-coupling reactions of bis N-methyliminodiacetic
    acid (MIDA) boronate ester substituted arylamines
    with dibromo arenes. The roles of solvent composition, temperature,
    reaction time, and co-monomer structure were examined
    and (co)polymers prepared containing 9, 9-dioctylfluorene
    (F8), 4-sec-butyl or 4-octylphenyl diphenyl amine, and N, N0-
    bis(4-octylphenyl)-N, N0-diphenyl phenylenediamine units,
    using Pd(OAc)2/2-dicyclohexylphosphino-20,60-dimethoxybiphenyl (SPhos) catalyst system. The performance of a difunctionalized MIDA boronate ester monomer was compared
    with that of an equivalent pinacol boronate ester. Higher molar
    mass polymers were produced from reactions starting with a
    difunctionalized pinacol boronate ester monomer than the
    equivalent difunctionalized MIDA boronate ester monomer in
    biphase solvent mixtures (toluene/dioxane/water). Matrixassisted
    laser desorption/ionization mass spectroscopic analysis
    revealed that polymeric structures rich in residues associated
    with the starting MIDA monomer were present,
    suggesting that homo-coupling of the boronate ester must be
    occurring to the detriment of cross-coupling in the step-growth
    polymerization. However, when comparable reactions of the
    two boronate monomers with a dibromo fluorene monomer
    were completed in a single phase solvent mixture (dioxane1
    water), high molar mass polymers with relatively narrow distribution ranges were obtained after only 4 h of reaction
    Original languageEnglish
    JournalJournal of Polymer Science. Part A: Polymer Chemistry
    Early online date3 Jul 2017
    DOIs
    Publication statusPublished - 2017

    Keywords

    • N-methyliminodiacetic acid (MIDA) boronate esters
    • polytriarylamines
    • Suzuki cross-coupling polymerization

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