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

J Polym Sci A Polym Chem. 2017 Sep 1;55(17):2798-2806.

PMID: 28979067

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. © 2017 The Authors. Journal of Polymer Science Part A: Polymer Chemistry Published by Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2798-2806.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP863992567	9,10-Anthracenediboronic acid bis(pinacol) ester		863992-56-7	Price

Catalog Number

Product Name

Structure

CAS Number

Price

AP863992567

9,10-Anthracenediboronic acid bis(pinacol) ester

863992-56-7

Price

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