Self-assembling carbohydrate-functionalized oligothiophenes

Org Lett. 2009 Nov 19;11(22):5098-101. doi: 10.1021/ol9022694.

Abstract

Carbohydrate-functionalized oligothiophenes have been synthesized applying mild Sonogashira cross-coupling conditions. In an aqueous environment the amphiphilic hybrids self-assemble into chiral superstructures as a result of multiple hydrogen bond interactions and the helicity of the aggregates is controllable by the configuration of the carbohydrate unit. By means of atomic force microscopy highly ordered layer arrangements on substrates were characterized.

MeSH terms

  • Carbohydrates / chemistry*
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Conformation
  • Particle Size
  • Surface Properties
  • Thiophenes / chemical synthesis*
  • Thiophenes / chemistry*

Substances

  • Carbohydrates
  • Thiophenes