Water-soluble resorcin[4]arene: Complexation of anionic aromatic guests by cooperativity of electrostatic and hydrophobic interactions

Abstract

Water-soluble resorcin[4]arene based cavitand 2 was synthesized by reaction of bromomethylcavitand 1 with hexamethylenetetramine. The bowl-shaped cavitand host 2 shows a good binding affinity to anionic aromatic guests with 1:1 binding in D2O. The guest inclusion within the host cavity was confirmed by H-1 NMR spectroscopy. Electrostatic interaction as well as hydrophobic interaction turned out to cooperatively act as binding forces for a strong complex formation in water. (C) 1999 Elsevier Science Ltd. All rights reserved.