Enantioselective extraction mediated by a chiral cavitand-salen covalently assembled on a porous silicon surface

Chem Commun (Camb). 2014 May 21;50(39):4993-6. doi: 10.1039/c4cc00034j. Epub 2014 Feb 6.

Abstract

A chiral organic-inorganic hybrid material, based on a porous silicon surface functionalized with a chiral cavitand, was designed and synthesized. The affinity of this device in water toward a bromine-marked alkyl-ammonium salt has been evaluated using XPS detection. UV and CD measurements highlight the enantioselective extraction from a racemic mixture in water of the S-enantiomer of the selected guest (ee ≥ 80%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromine / chemistry*
  • Circular Dichroism
  • Ethers, Cyclic / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Photoelectron Spectroscopy
  • Porosity
  • Quaternary Ammonium Compounds / chemistry
  • Quaternary Ammonium Compounds / isolation & purification*
  • Resorcinols / chemistry*
  • Silicon / chemistry*
  • Stereoisomerism
  • Surface Properties
  • Water / chemistry*

Substances

  • Ethers, Cyclic
  • Quaternary Ammonium Compounds
  • Resorcinols
  • cavitand
  • Water
  • Bromine
  • Silicon