Green synthesis of polycyclic benzimidazole derivatives and organic semiconductors

Org Lett. 2011 Sep 16;13(18):4882-5. doi: 10.1021/ol201973w. Epub 2011 Aug 24.

Abstract

Polycyclic benzimidazole derivatives, an important class of compounds in organic electronics and photovoltaics, were prepared using a solvent-free "green" process based on heating carboxylic acid anhydrides and arylene diamines in the presence of zinc acetate in the solid state. Products were isolated and purified directly by train sublimation of the crude reaction mixtures. The reaction conditions were optimized using various carboxylic acid anhydrides. Optical and electrochemical properties of these materials are also described.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry
  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Conformation
  • Polycyclic Aromatic Hydrocarbons / chemical synthesis*
  • Polycyclic Aromatic Hydrocarbons / chemistry
  • Semiconductors
  • Stereoisomerism

Substances

  • Benzimidazoles
  • Polycyclic Aromatic Hydrocarbons
  • benzimidazole