Sulfonamide carbazole receptors for anion recognition

Org Biomol Chem. 2011 Dec 21;9(24):8321-7. doi: 10.1039/c1ob06126g. Epub 2011 Nov 7.

Abstract

Carbazole-based receptors functionalized with two sulfonamide groups have been synthesized and their properties as anion receptors have been evaluated. The receptor with bis(trifluoromethyl)aniline groups has shown a very high affinity for halide ions, especially remarkable as only two hydrogen bonds are formed in the complexes. (1)H NMR and fluorescence titrations have been carried out and binding constants up to 7.9 × 10(6) M(-1) have been reached. X-ray structures have been obtained and a modelling study has shown the possible reasons for the large affinity of these compounds for halide anions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemical synthesis
  • Anions / chemistry
  • Carbazoles / chemical synthesis
  • Carbazoles / chemistry*
  • Crystallography, X-Ray
  • Fluorescence
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism
  • Sulfonamides / chemistry*

Substances

  • Anions
  • Carbazoles
  • Sulfonamides
  • carbazole