Issue 4, 1999

Synthesis and aggregation of two-headed surfactants bearing amino acid moieties

Abstract

The synthesis of bolaamphiphiles with two amino acid heads having the general structure AA–X–AA, where AA denotes an amino acid (D- or L-alanine or L-histidine) and X an alkyl chain of varying length, is described. Micellization was observed for the bolaamphiphile with a twenty-carbon atom alkyl chain. For compounds with shorter chain lengths, light scattering and electron microscopy suggest the formation of vesicles or fibrous aggregates. These bolaamphiphiles can also form gels at higher concentrations in water or ethanol. Fibrous structures were observed in these gels by electron microscopy. Synthèse et agre′gation d'amphiphiles àdeux têtes portant un motif acide amine′. Des bolaamphiphiles de structure AA–X–AA, où AA repre′sente un motif acide amine′ (D- ou L-alanine ou L-histidine) et X est un segment lipophile de longueur variable, ont e′te′ synthe′tise′s. Les phe′nomènes d'agre′gation en solution aqueuse de ces bolaformes ont e′te′ e′tudie′s. Seuls les compose′s pre′sentant une longueur de chaîne de vingt atomes de carbone forment des micelles. Pour les bolaamphiphiles ayant des chaînes hydrocarbone′es plus courtes la formation de ve′sicules, de fibres ou d'he′lices est observe′e diffusion de la lumière et microscopie e′lectronique. Ces bolaamphiphiles à motif acide amine′ forment aussi des gels dans l'e′thanol ou dans l'eau. Dans ce cas, des structures fibreuses ont pu être observe′es par microscopie e′lectronique.

Supplementary files

Article information

Article type
Paper

New J. Chem., 1999,23, 447-452

Synthesis and aggregation of two-headed surfactants bearing amino acid moieties

S. Franceschi, N. de Viguerie, M. Riviere and A. Lattes, New J. Chem., 1999, 23, 447 DOI: 10.1039/A809079C

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