Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 18, Pages 5656-5669Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200701897
Keywords
amino sugars; amphliphiles; gels; liquid crystals; self-assembly
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This article describes the systematic preparation of a novel family of carbohydrate amphiphiles and bolaamphiphiles in which hydrophilic and hydrophobic units are connected via a ureido or bis(ureido) moiety. The sugar core is derived from aminopolyols such as D-glucamine (1), N-methyl-D-glucamine (2), or the sugar-like species tris(hydroxymethyl)aminomethane (3). The O-unprotected derivatives behave as self-organizing nonionic surfactants with good water gelation ability, which can be induced under thermal or ultrasound-driven stimuli. In addition, some derivatives of 1 and 2, and rarely 3 also formed lyotropic liquid crystals with lamellar or hexagonal structures that exhibit low-temperature transitions.
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