Biomimetic Studies Using Astificial Systems. V. : Design and Synthesis of Novel Water-Soluble Bis-cyclophanes

Abstract

Novel water-soluble bis-cyclophanes (3a-c) with quaternary ammonium nitrigens, composed of two untis of QCP44 (2) connected by appropriate bridges, were synthesized as hosts having two discrete hydrophobic cavities to bind two guest molecules simultaneously or a single guest molecule via double recognition in neutral water. Glutaryl, terephthaloyl and isophthaloyl groups were used as spacers to bridge the two cyclophane units. THe bridge formation was carried out using 5 as an intermediate, in which three of the four nitrogens of CP44 (1) were protected. The details of the synthesis and characterization of duplex hosts (3a-c) as well as of the reference compounds (9-11) are described.