P-tert-Butyl thiacalix[4]arenes functionalized at the lower rim by amide, hydroxyl and ester groups as anion receptors

Abstract

New p-tert-butyl thiacalix[4]arenes differently substituted at the lower rim with amide, hydroxyl and ester groups were synthesized. Binding properties of the compounds toward some tetrabutylammonium salts n-Bu4NX (X = F-, Cl-, Br-, I-, CH 3CO2 -, H2PO4 -, NO3 -) were studied by UV spectroscopy. It was found that the stoichiometry of the complexes, generally, is 1:1, and the association constants are in the range of 103-105 M-1. The p-tert-butyl thiacalix[4]arenes containing secondary amide groups trisubstituted at the lower rim bind the studied anions most effectively. Selective receptors for fluoride and dihydrogen phosphate salts of tetrabutylammonium were found. © 2011 The Royal Society of Chemistry