A General Protocol for the Polycondensation of Thienyl N-Methyliminodiacetic Acid Boronate Esters to Form High Molecular Weight Copolymers

Josue Ayuso Carrillo, Michael L. Turner*, Michael J. Ingleson

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Thienyl di-N-methyliminodiacetic acid (MIDA) boronate esters are readily synthesized by electrophilic C-H borylation producing bench stable crystalline solids in good yield and excellent purity. Optimal conditions for the slow release of the boronic acid using KOH as the base in biphasic THF/water mixtures enables the thienyl MIDA boronate esters to be extremely effective homo-bifunctionalized (AA-type) monomers in Suzuki-Miyaura copolymerizations with dibromo-heteroarenes (BB-type monomers). A single polymerization protocol is applicable for the formation of five alternating thienyl copolymers that are (or are close analogues of) state of the art materials used in organic electronics. The five polymers were produced in excellent yields and with high molecular weights comparable to those produced using Stille copolymerization protocols. Therefore, thienyl di-MIDA boronate esters represent bench stable and low toxicity alternatives to highly toxic di-trimethylstannyl AA-type monomers that are currently ubiquitous in the synthesis of these important alternating copolymers.

Original languageEnglish
Pages (from-to)13361-13368
Number of pages8
JournalJournal of the American Chemical Society
Volume138
Issue number40
Early online date29 Sep 2016
DOIs
Publication statusPublished - 12 Oct 2016

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