SYNTHESIS AND AGGREGATION BEHAVIOR OF 2-HEADED SURFACTANTS CONTAININGTHE UROCANIC ACID MOIETY

Urocanic acid (3-[1H-imidazol-4-yl]propenoic acid) has attracted great interest in photobiology for many years. We describe here the synthes is of three bolaamphiphiles with two urocanic acid heads having the ge neral structure: UA-X-UA, where UA denotes urocanic acid and X is an a lkyl chain of varying length. We show that micellisation occurs with t he bolaamphiphile whose alkyl chain length is sixteen carbon atoms. Fo r compounds having a shorter chain length, light scattering and electr on microscopy suggest the formation of vesicles. Compared to urocanic acid, the bolaamphiphiles, which can form aggregates in aqueous soluti on, may act differently on membranes and be used in formulations more easily.