Thienyl MIDA Boronate Esters as Highly Effective Monomers for Suzuki-Miyaura Polymerization Reactions

Research output: Contribution to journalArticle

Abstract

The synthesis of highly regioregular poly(3-hexylthiophene-2,5-diyl), rr-P3HT, by Suzuki–Miyaura polymerization is reported. The key N-methyliminodiacetic acid (MIDA) boronate ester thienyl monomer was synthesized using a one-pot multigram scale procedure, in high purity, and in good isolated yield (80%) by direct electrophilic borylation. Conditions for the hydrolysis of the MIDA protecting group and the polymerization reaction were investigated. The optimal procedure gave rr-P3HT with >98% HT couplings, excellent isolated yields (up to 94%), and polymer molecular weights up to Mn = 18.7 kDa and Mw = 42.7 kDa. The performance of the MIDA containing monomer was compared to that of the pinacol boronate ester under identical polymerization conditions, with the latter producing lower molecular weight polymers in reduced yield.

Bibliographical metadata

Original languageEnglish
Pages (from-to)979-986
Number of pages7
JournalMacromolecules
Volume48
Issue number4
DOIs
StatePublished - 10 Feb 2015