N. Boden et al., ALPHA-HALOGENATION OF TRIPHENYLENE-BASED DISCOTIC LIQUID-CRYSTALS - TOWARDS A CHIRAL NUCLEUS, Journal of materials chemistry, 7(4), 1997, pp. 601-605
In an attempt to prepare chiral discotic liquid crystals based on a he
lically twisted triphenylene nucleus a route has been developed for th
e introduction of a-fluoro, -chloro and -bromo substituents and it is
shown that multiple alpha-halogenation is also possible. The monosubst
ituted derivatives all show enhanced mesophase stability whilst format
ion of the mesophase is suppressed for the polyhalogenated derivatives
. Rather surprisingly, reaction of 2,3,6,7,10,11-hexahexyloxytriphenyl
ene (HAT6) with iodine monochloride results in chlorination rather tha
n iodination.