N,N-Didansyl-4,13-diaza-18-Crown-6: A Fluorescence-sensitive, Weakly Complexing Macrocycle Used to Probe the Phospholipid Vesicle Environment

Abstract

N, N-Didansyl-4, 13-diaza-18-crownh-a6s been prepared and characterized by standard chemical techniques. The fluorescence emission of the dansyl sidearms are sensitive to the environment and the macrocycle has been used to probe the interior of a phospholipid bilayer. An experiment to probe the environment experienced by metal cation complexes of this macrocycle failed, apparently due to its extremely low cation binding strength. This macrocycle was also ineffective in transporting Na⁺ through a bulk CHC1₃ membrane. A solid state structure of the free macrocycle suggests why binding is so poor for this compound.