Palladium-catalyzed dehydrohalogenative polycondensation of 2-bromo-3-hexylthiophene: an efficient approach to head-to-tail poly(3-hexylthiophene)

J Am Chem Soc. 2010 Aug 25;132(33):11420-1. doi: 10.1021/ja105767z.

Abstract

Dehydrohalogenative polycondensation of 2-bromo-3-hexylthiophene was successful with Herrmann's catalyst and tris(2-dimethylaminophenyl)phosphine as catalyst precursors, giving head-to-tail poly(3-hexylthiophene) (HT-P3HT) with high molecular weight (M(n) = 30,600, M(w)/M(n) = 1.60) and high regioregularity (98%) in almost quantitative yield (99%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Stereoisomerism
  • Thiophenes / chemical synthesis*
  • Thiophenes / chemistry*

Substances

  • 2-bromo-3-hexylthiophene
  • Organometallic Compounds
  • Thiophenes
  • poly(3-hexylthiophene)
  • Palladium