A bambusuril macrocycle that binds anions in water with high affinity and selectivity

Angew Chem Int Ed Engl. 2015 Jan 2;54(1):276-9. doi: 10.1002/anie.201409895. Epub 2014 Nov 10.

Abstract

Synthetic receptors that function in water are important for the qualitative and quantitative detection of anions, which may act as pollutants in the environment or play important roles in biological processes. Neutral receptors are particularly appealing because they are often more selective than positively charged receptors; however, their affinity towards anions in pure water is only in range of 1-10(3) L mol(-1) . The anion-templated synthesis of a water-soluble bambusuril derivative is shown to be an outstanding receptor for various inorganic anions in pure water, with association constants of up to 10(7) L mol(-1) . Furthermore, the macrocycle discriminates between anions with unprecedented selectivity (up to 500 000-fold). We anticipate that the combination of remarkable affinity and selectivity of this macrocycle will enable the efficient detection and isolation of diverse anions in aqueous solutions, which is not possible with current supramolecular systems.

Keywords: anion recognition; host-guest systems; macrocycles; self-assembly; supramolecular chemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / analysis
  • Anions / isolation & purification*
  • Binding Sites
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry*
  • Macrocyclic Compounds / chemical synthesis
  • Macrocyclic Compounds / chemistry*
  • Models, Molecular
  • Water / analysis*

Substances

  • Anions
  • Imidazoles
  • Macrocyclic Compounds
  • bambus(6)uril
  • Water