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

Abstract:

:Seven members of the methyl-6-O-(n-acyl)-α-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.

journal_name

Chem Phys Lipids

authors

Cook AG,Wardell JL,Imrie CT

doi

10.1016/j.chemphyslip.2010.11.007

subject

Has Abstract

pub_date

2011-02-01 00:00:00

pages

118-24

issue

2

eissn

0009-3084

issn

1873-2941

pii

S0009-3084(10)00376-2

journal_volume

164

pub_type

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