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Stereospecific Synthesis of New Trioxadecalin‐Derived Liquid Crystals Bearing Halogen Substituents on the Phenyl Ring
Author(s) -
Bertini Bruno,
Moineau Christophe,
Sinou Denis,
Gesekus Gunnar,
Vill Volkmar
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200101)2001:2<375::aid-ejoc375>3.0.co;2-j
Subject(s) - chemistry , mesogen , aryl , alkoxy group , glucal , stereospecificity , halogen , stereochemistry , crystallography , catalysis , phase (matter) , organic chemistry , liquid crystalline , alkyl
Reaction of pseudo‐glucal 2 with various aryl Grignard reagents bearing halogen substituents, in the presence of a catalytic amount of NiCl 2 (dppe) gives the corresponding β‐ C ‐aryl glycosides 4 . Deacetylation and hydrogenation of 4 leads to the β‐ C ‐aryl glycosides 5 , which can be used as chiral compounds in the synthesis of chiral liquid crystals. The reaction of compound 5 with aliphatic aldehydes leads to compounds 6 ; similarly, reaction with p ‐alkoxy‐substituted phenylboronic acids gives the bora analogues 7 . All the mesogenic properties depend strongly on small changes in the molecular structure. It is possible to obtain a wide array of different chiral effects such as helix inversion, blue phase, TGA phase, cholesteric phase, and smectic A phase, to name but a few, by changing a small part of the molecule while maintaining the basic mesogenic core.