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Benzodithiophene homopolymers via direct (hetero) arylation polymerization
Polymer Bulletin (2018)
  • Calvin L Cicha
  • Samuel N Gockel
  • Andrew J Helmin
  • Wyatt D Wilcox
  • Daron E Janzen, St. Catherine University
  • Ted M. Pappenfus, University of Minnesota
Abstract
Direct (hetero)arylation polymerization (DHAP) of a monobrominated
benzo[1,2-b:4,5-b′]dithiophene monomer using the Herrmann–Beller catalyst with a tertiary phosphine provided benzodithiophene homopolymers in good yields. Employing both P(o-OMePh)3 and P(o-NMe2Ph)3 as the phosphine ligands gave well-defined polymers—with the later phosphine providing a higher molecular weight polymer. The preparation of a benzodithiophene (BDT) trimer was used to
assist in the assignment of the 1H NMR spectra of the synthesized polymers which show largely defect-free couplings. The optical spectra of polymers formed via DHAP and those prepared using traditional Stille couplings are essentially identical, which further confirms the presence of well-defined BDT–BDT couplings along the
conjugated polymer chain. These results confirm that carboxylic acid additives are not always necessary to suppress defects in DHAP polymerizations and that DHAP is a viable alternative to traditional Stille coupling for the preparation of benzodithiophene homopolymers.
Disciplines
Publication Date
May 8, 2018
DOI
10.1007/s00289-018-2346-6
Citation Information
Calvin L Cicha, Samuel N Gockel, Andrew J Helmin, Wyatt D Wilcox, et al.. "Benzodithiophene homopolymers via direct (hetero) arylation polymerization" Polymer Bulletin Iss. 12 (2018)
Available at: http://works.bepress.com/daron-janzen/93/