Syntheses and aggregate study of bisphenol-containing diaza-18-crown-6 ligands

Bisphenol-containing diaza-18-crown-6 ligands (1-16) were synthesized as po tential membrane-forming amphiphiles via the one-pot Mannich reaction. Soni cation of the crude products in a small amount of MeOH followed by filtrati on and drying proved to be an efficient method of purifying nearly all comp ounds. Compounds 8 and 9 were selected for assay as amphiphiles. Compared t o simple, alkylated diazacrown ethers, the stability of the amphisomes form ed from these monomers is lower possibly because intramolecular hydrogen bo nding prevents formation of intermolecular hydrogen bonds. (C) 1999 Elsevie r Science Ltd. All rights reserved.