Carbohydrate liquid crystals: synthesis and characterisation of the methyl-6-O-(n-acyl)-α-D-glucopyranosides

Andrew G. Cook, James L. Wardell, Corrie T. Imrie

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Seven members of the methyl-6-O-(n-acyl)-alpha-D-glucopyranosides have been synthesised and their transitional properties determined. The undecanoyl and octadecanoyl members do not exhibit liquid crystallinity while the members having chain lengths between dodecanoyl and hexadecanoyl exhibit a monotropic smectic A phase. Variable temperature infrared spectroscopy reveals that the hydrogen bonding within the system shows a marked change at the melting point but apparently no change at the smectic A-isotropic transition. This observation is interpreted in terms of Goodby's model for the smectic A phase in which the carbohydrate moieties are located at the centre of the smectic bilayer and assuming that hydrogen bonded aggregates persist into the isotropic phase. Within this framework, the unusually low values of the entropy change associated with the smectic A-isotropic transition may also be accounted for. (C) 2010 Published by Elsevier Ireland Ltd.

Original languageEnglish
Pages (from-to)118-124
Number of pages7
JournalChemistry and Physics of Lipids
Volume164
Issue number2
DOIs
Publication statusPublished - Feb 2011

Keywords

  • liquid crystals
  • smectic A phase
  • variable temperature FTIR
  • hydrogen bonding
  • glycosyl dialkyl-glycerols
  • branched alkyl chains
  • homologous seriesSERIES
  • mesomorphic properties
  • mesogenic properties
  • fatty-acid
  • D-glucose
  • behavior
  • derivatives
  • glycolipids

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