Use of N-methyliminodiacetic acid boronate esters in suzuki-miyaura cross-coupling polymerizations of triarylamine and fluorene monomers

Andrew B. Foster*, Viktor Bagutski, Josue I. Ayuso-Carrillo, Martin J. Humphries, Michael J. Ingleson, Michael L. Turner

*Corresponding author for this work

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 (TFB), and N, N′-bis(4-octylphenyl)-N, N′-diphenyl phenylenediamine (PTB) units, using a Pd(OAc)2/2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) catalyst system. The performance of a di-functionalized 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). Matrix-assisted 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 (dioxane + water), high molar mass polymers with relatively narrow distribution ranges were obtained after only 4 h of reaction.

Original languageEnglish
Pages (from-to)2798-2806
Number of pages9
JournalJournal of Polymer Science Part A: Polymer Chemistry
Volume55
Issue number17
Early online date3 Jul 2017
DOIs
Publication statusE-pub ahead of print - 3 Jul 2017

Keywords

  • conjugated polymers
  • N-methyliminodiacetic acid (MIDA) boronate esters
  • polytriarylamines
  • step-growth polymerization
  • suzuki cross-coupling polymerization
  • suzuki polycondensation

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