Nickel-Catalyzed Suzuki Polycondensation for Controlled Synthesis of Ester-Functionalized Conjugated Polymers

Yunyan Qiu, Joshua C. Worch, Andria Fortney, Chakicherla Gayathri, Roberto R. Gil, Kevin J.T. Noonan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

Controlled synthesis of conjugated polymers with functional side chains is of great importance, affording well-defined optoelectronic materials possessing enhanced stability and tunability as compared to their alkyl-substituted counterparts. Herein, a chain-growth Suzuki polycondensation of an ester-functionalized thiophene is described using commercially available nickel precatalysts. Model compound studies were used to identify suitable catalysts, and these experiments provided guidance for the polymerization of the ester-substituted monomer. This is the first report of nickel-catalyzed Suzuki cross-coupling for catalyst-transfer polycondensation, and to further illustrate the versatility of this method, block and alternating copolymers with 3-hexylthiophene were synthesized. The presented protocol should serve as an entry point into the synthesis of other electron-deficient polymers and donor-acceptor copolymers with controlled molecular weights and low dispersity.

Original languageEnglish (US)
Pages (from-to)4757-4762
Number of pages6
JournalMacromolecules
Volume49
Issue number13
DOIs
StatePublished - Jul 12 2016
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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