Aryne polymerization enabling straightforward synthesis of elusive poly(ortho-arylene)s

J Am Chem Soc. 2015 Jan 14;137(1):74-7. doi: 10.1021/ja5112207. Epub 2014 Dec 26.

Abstract

Herein we present the first straightforward aryne polymerization that successively connects aromatic rings at their ortho-positions, directly giving poly(ortho-phenylene)s of up to ca. 100-mer size. The polymerization proceeds smoothly in a chain-growth fashion in the presence of a monovalent copper reagent. Direct synthesis of poly(ortho-arylene)s has been a "missing piece" of aromatic chemistry for a long time (although the discovery of arynes dates back to 1902), in contrast to the well-investigated para- and meta-linked polyarylenes. Our achievement reported here is expected to open up new areas of nanocarbon and materials science.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrocarbons, Aromatic / chemical synthesis*
  • Hydrocarbons, Aromatic / chemistry
  • Molecular Structure
  • Polymerization
  • Polymers / chemical synthesis*
  • Polymers / chemistry
  • Quantum Theory

Substances

  • Hydrocarbons, Aromatic
  • Polymers