Synthesis and mesomorphic properties of glycosyl dialkyl- and diacyl-glycerols bearing saturated, unsaturated and methyl branched fatty acid and fatty alcohol chains. Part II. Mesomorphic properties.
The biophysical properties of a series of glycosyl dialkyl- and diacyl-glycerols bearing unsaturated or chiral methyl branched chains in the tail, and di- and trisaccharide carbohydrate headgroups are described. Thermotropism was investigated by polarising microscopy, the lyotropism was investigated by small angle X-ray diffraction and by the contact preparation method, and the gel to liquid crystalline phase transition by FT-IR-spectroscopy. The compounds displayed thermotropic Smectic A (SmA), cubic and columnar phases, whereas in the lyotropic phase diagram lamellar, hexagonal and cubic phases are found. The introduction of unsaturated or methyl branched chains leads to liquid crystallinity at ambient temperature. The difference between the 1,3-oleyl-glycerol maltoside and the corresponding 1,2-oleoyl-glycerol maltoside is small.
Milkereit
Götz
G
Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany.
Brandenburg
Klaus
K
Gerber
Sven
S
Koch
Michel H J
MH
Morr
Michael
M
Andrä
Jörg
J
Seydel
Ulrich
U
Vill
Volkmar
V
D000215:Acylation; D000478:Alkylation; D001672:Biocompatible Materials / Q000032:analysis / Q000138:chemical synthesis; D003460:Crystallization / Q000379:methods*; D003461:Crystallography; D005227:Fatty Acids / Q000032:analysis* / Q000138:chemical synthesis*; D005233:Fatty Alcohols / Q000032:analysis* / Q000138:chemical synthesis*; D005990:Glycerol / Q000032:analysis* / Q000138:chemical synthesis*; D008968:Molecular Conformation; D044367:Phase Transition; D013696:Temperature
D001672:Biocompatible Materials; D005227:Fatty Acids; D005233:Fatty Alcohols; D005990:Glycerol