SYNTHESIS AND LIQUID CRYSTALLINE PROPERTIES OF THE n-ALKYL 1-THIO-α-D-GLUCOPYRANOSIDES, A NEW HOMOLOGOUS SERIES OF CARBOHYDRATE MESOGENS

Article abstract of DOI:10.1016/0008-6215(89)85007-4

The n-alkyl 1-thio-α-D-glucopyranosides (n-propyl to n-dodecyl) were prepared by treating 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose with an alkanethiol in the presence of boron trifluoride etherate followed by deacetylation.The n-propyl and n-butyl derivatives are not thermotropic, the n-pentyl derivative is monotropic, and the compounds with n-hexyl and longer alkyl chains are enantiotropic, the largest liquid crystalline range being from +/- 100-175 deg for the n-undecyl derivative.The transition point data are typical for smectic behavior, and X-ray data and texture observations are indicative of a smectic A_d phase.