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Amphiphilic and Mesogenic Carbohydrates, 8 . – Liquid Crystalline Alkyl 2‐Deoxy‐2‐fluoro‐1‐thioglycopyranosides
Author(s) -
Miethchen Ralf,
Kowalek Heike,
Niemanna Angela,
Diele Siegmar,
Schick Christoph
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970140
Subject(s) - alkyl , chemistry , mesogen , homologous series , amphiphile , glycosyl , thio , liquid crystal , stereochemistry , crystallography , polymer chemistry , organic chemistry , liquid crystalline , copolymer , phase (matter) , materials science , optoelectronics , polymer
The homologous series of the amphiphilic alkyl 2‐deoxy‐2‐fluoro‐1‐thio‐α‐ D ‐glucopyranosides 5a–e and alkyl 2‐deoxy‐2‐fluoro‐1‐thio‐α‐ D ‐mannopyranosides 9a–e were prepared from the 2‐deoxy‐2‐fluoro‐ D ‐glycosyl fluorides 1 and 6 , respectively. Their liquid crystalline properties were investigated by polarising microscopy, DSC measurements, and X‐ray measurements. The fluorine‐containing thioglycosides 5a–e as well as 9a–e form enantiotropic mesophases of the type smectic A. The effects of F for OH and S for O substitution are discussed with reference to the homologous alkyl‐1‐thio‐α‐ D ‐glucopyranosides 10 and alkyl 2‐deoxy‐2‐fluoro‐α‐ D ‐glucopyranosides 11 .