Indole-7-amine was investigated as an alternative to aniline in construction of amide-based anion receptors. Replacement of aniline with indolamine introduces additional binding site-indolyl NH, which can enhance anion binding for more than five times. The molecular modelling of indole-containing receptors revealed the correlation between their conformational preferences and their affinity towards anions. (c) 2007 Elsevier Ltd. All rights reserved.