Synthesis of Polyfuran and Thiophene-Furan Alternating Copolymers Using Catalyst-Transfer Polycondensation

Yunyan Qiu, Andria Fortney, Chia Hua Tsai, Matthew A. Baker, Roberto R. Gil, Tomasz Kowalewski, Kevin J.T. Noonan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

52 Scopus citations

Abstract

There is intense interest in the rational design of semiconducting materials to improve organic electronics. Furan is a particularly attractive monomer for building biorenewable and biodegradable π-conjugated frameworks. In this report, regioregular head-to-tail and head-to-head poly(3-hexylfuran) were synthesized using chain-growth polycondensation. The resultant polyfurans have relatively low molecular weights but also low dispersities. The head-to-head polyfuran adopted a nearly identical coplanar backbone conformation as its head-to-tail analog in the solid state, as determined by UV-visible spectroscopy and atomic force microscopy. Extensive aggregation of the furan homopolymer during polymerization led to the investigation of an alternating furan-thiophene copolymer, confirming that furyl-based monomers can polymerize in a chain-growth manner. All of the synthesized polymers are sensitive when exposed to both oxygen and light. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)332-336
Number of pages5
JournalACS Macro Letters
Volume5
Issue number3
DOIs
StatePublished - Mar 15 2016
Externally publishedYes

ASJC Scopus subject areas

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

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