QUINONE-CONTAINING AMPHIPHILES AND BOLAFORM AMPHIPHILES THAT FORM REDOX-ACTIVE LIPID-MEMBRANES

Amphiphiles containing quinone moieties were developed in order to fix electron acceptors at the outer surface or in the center of vesicle membranes. A double-chain amphiphile with sulfonated quinone head group formed stable vesicles. Sodium borohydride reduced only their outer surfaces. A single-chain bolaform amphiphile (bolaamphiphile) gave unsymmetric monolayered vesicles where all the quinone head groups were located on the outer surface. A dicationic bolaamphiphile with a non-polar quinone in the center was localized in the center of a negatively charged dihexadecyl phosphate vesicle membrane. Some similar membrane systems, where the quinone rings remained mobile, are also shortly described. It was also found that a semiquinone of a macrocyclic bolaamphiphile containing two benzoquinone moieties was long-lived in vesicular membranes. © 1990 American Chemical Society.