Synthesis and membrane activity of a bis(metacyclophane)bolaamphiphile.

The synthesis of macrocyclic tetraesters from 5-substituted isophthalic acids and 1,8-octane diol gave macrocylic metacyclophanes with the axially symmetric positions differentially protected. Dimer bis(metacyclophane)bolaamphiphiles proved to be extremely insoluble, but one derivative was shown to have significant membrane activity. Very high continuous conductance and the formation of discrete single-ion channels were both observed, depending on how the compound was incorporated into the bilayer membrane.