Bis(imidazolium)-calix[4]arene receptors for anion binding

J Org Chem. 2009 Jan 2;74(1):482-5. doi: 10.1021/jo8023285.

Abstract

Efficient access to the bis(imidazolyl)calixarene 2 and dicationic bis(imidazolium) salts 1a,b x 2X directly bonded to the upper rim of calixarene structure has been reported. Anion binding properties of the new receptors were studied by 1H NMR spectroscopic methods. Bis(N-butylimidazolium) dication 1a exhibited the best recognition properties toward carboxylate anions with a 1:1 receptor-anion binding stoichiometry, whereas the presence of a bulky group such as isopropyl (1b) increased the difficulty of both imidazolium moieties to be able to support the association with the same single anion.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemistry
  • Binding Sites
  • Calixarenes / chemical synthesis
  • Calixarenes / chemistry*
  • Catalysis
  • Copper / chemistry
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry*
  • Iodides / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Phenols / chemical synthesis
  • Phenols / chemistry*

Substances

  • Anions
  • Imidazoles
  • Iodides
  • Phenols
  • calix(4)arene
  • Calixarenes
  • Copper
  • cuprous iodide