Synthesis and aggregation behaviour of two-headed surfactants containing the 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 synthesis of three bolaamphiphiles with two urocanic acid heads having the general structure: UA-X-UA, where UA denotes urocanic acid and X is an alkyl chain of varyin...

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Bibliographic Details
Published inNew journal of chemistry Vol. 22; no. 3; pp. 225 - 231
Main Authors Franceschi, S, Andreu, de Viguerie, N, Riviere, M, Lattes, A, Moisand, A
Format Journal Article
LanguageEnglish
Published PARIS Elsevier 1998
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
SELF-ASSOCIATION
MICELLAR PROPERTIES
BOLAFORM DETERGENTS
VESICLE FORMATION
CHEMICAL RELAXATION
BOLAAMPHIPHILES
MONOLAYER LIPID-MEMBRANES
AMPHIPHILES
ULTRAVIOLET-IRRADIATION
AQUEOUS-SOLUTION
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Summary:Urocanic acid (3-[1H-imidazol-4-yl]propenoic acid) has attracted great interest in photobiology for many years. We describe here the synthesis of three bolaamphiphiles with two urocanic acid heads having the general structure: UA-X-UA, where UA denotes urocanic acid and X is an alkyl chain of varying length. We show that micellisation occurs with the bolaamphiphile whose alkyl chain length is sixteen carbon atoms. For compounds having a shorter chain length, light scattering and electron microscopy suggest the formation of vesicles. Compared to urocanic acid, the bolaamphiphiles, which can form aggregates in aqueous solution, may act differently on membranes and be used in formulations more easily.
ISSN:1144-0546
1369-9261
DOI:10.1039/a708326b