One-step synthesis of low molecular weight poly(p-phenyleneethynylenevinylene)s via polyaddition of aromatic diynes by catalysis of the [Ru(p-cymene)Cl2]2/AcOH system

J Org Chem. 2008 May 16;73(10):3892-9. doi: 10.1021/jo800471p. Epub 2008 Apr 15.

Abstract

pi-Conjugated low molecular weight polymers characterized by regio- and stereoregular alternation of phenylene and ( E)-1-en-3-yne moieties have been synthesized by polyaddition of 1,4-diethynylbenzene or of 2,5-diethynyl-1,4-alkoxybenzene monomers, employing the commercially available di-micro-chlorobis[( p-cymene)chlororuthenium(II)] complex as the metal catalyst source, under homogeneous, atom-economical, amine- and phosphine-free conditions. Bulk materials of poly( p-phenyleneethynylenevinylene) derivatives are obtained with yields larger than 80%, from which polymers readily soluble in chlorinated solvents and in tetrahydrofuran are extracted in 60-75% yields. The polymers with average degrees of polymerization in the range n AV = 4-8 display optical properties in solution similar to those of the higher molecular weights analogues.

MeSH terms

  • Acetates / chemistry*
  • Alkynes / chemical synthesis*
  • Alkynes / chemistry*
  • Catalysis
  • Cymenes
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Structure
  • Molecular Weight
  • Organometallic Compounds / chemistry*
  • Polystyrenes / chemical synthesis*
  • Polystyrenes / chemistry
  • Stereoisomerism

Substances

  • Acetates
  • Alkynes
  • Cymenes
  • Organometallic Compounds
  • Polystyrenes
  • dichloro(4-cymene)ruthenium(II)