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Mesogenic sugars : from aldoses to liquid crystals and surfactants

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Author: Doren, H.A. van · Smits, E. · Pestman, J.M. · Engberts, J.B.F.N. · Kellogg, R.M.
Institution: Centraal Instituut voor Voedingsonderzoek TNO
Source:Chemical Society Reviews, 3, 29, 183-199
Identifier: 71920
Keywords: Nutrition


Amphiphilic sugar derivatives, formed by condensation of functionalized aliphatic chains with aldoses, form liquid crystals, in most cases smectic. A puzzling observation was the failure of the S,S-acetals of 6-deoxy sugars, L-rhamnose and D-fucose, to form such phases. A satisfactory model to explain this behavior involves - in most cases - the formation of columns, which are destabilized with the deoxy sugars in which the apolar end methyl groups are pushed together. Despite the abundance of chiral centers in the mono-and disaccharides used the smectic phases themselves in general display no chirality. By appropriate molecular design in which the amphiphilic character was deliberately suppressed it was possible to prepare glucose derivatives that exhibit chiral nematic phases as well as impressive helical twisting powers. Simple condensation chemistry is used to produce such derivatives. The amphiphilic character can be deliberately enhanced, and this is readily achieved in double headed 'gemini' derivatives formed by condensation of glucose or lactose with a long chain diamine followed by reduction followed by acylation of the nitrogen atoms with long chain acyl anhydrides. The thermodynamics of micellization of precursors to these derivatives have been studied. The gemini derivatives themselves display remarkable properties including the formation of giant vesicles and an appreciable capacity for the solubilization of hydrocarbons.