a-Halogenation of triphenylene-based discotic liquid crystals: towards a chiral nucleus

Neville Boden; Richard J. Bushby; Andrew N. Cammidge; Sarah Duckworth; Gareth Headdock

doi:10.1039/A606447G

a-Halogenation of triphenylene-based discotic liquid crystals: towards a chiral nucleus

Neville Boden, Richard J. Bushby, Andrew N. Cammidge, Sarah Duckworth, Gareth Headdock

Synthetic and Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

98 Citations (Scopus)

Abstract

In an attempt to prepare chiral discotic liquid crystals based on a helically twisted triphenylene nucleus a route has been developed for the introduction of a-fluoro, -chloro and -bromo substituents and it is shown that multiple a-halogenation is also possible. The monosubstituted derivatives all show enhanced mesophase stability whilst formation of the mesophase is suppressed for the polyhalogenated derivatives. Rather surprisingly, reaction of 2,3,6,7,10,11-hexahexyloxytriphenylene (HAT6) with iodine monochloride results in chlorination rather than iodination.

Original language	English
Pages (from-to)	601-605
Number of pages	5
Journal	Journal of Materials Chemistry
Volume	7
Issue number	4
DOIs	https://doi.org/10.1039/A606447G
Publication status	Published - 1997

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10.1039/A606447G

Cite this

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abstract = "In an attempt to prepare chiral discotic liquid crystals based on a helically twisted triphenylene nucleus a route has been developed for the introduction of a-fluoro, -chloro and -bromo substituents and it is shown that multiple a-halogenation is also possible. The monosubstituted derivatives all show enhanced mesophase stability whilst formation of the mesophase is suppressed for the polyhalogenated derivatives. Rather surprisingly, reaction of 2,3,6,7,10,11-hexahexyloxytriphenylene (HAT6) with iodine monochloride results in chlorination rather than iodination.",

author = "Neville Boden and Bushby, {Richard J.} and Cammidge, {Andrew N.} and Sarah Duckworth and Gareth Headdock",

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T1 - a-Halogenation of triphenylene-based discotic liquid crystals: towards a chiral nucleus

AU - Boden, Neville

AU - Bushby, Richard J.

AU - Cammidge, Andrew N.

AU - Duckworth, Sarah

AU - Headdock, Gareth

PY - 1997

Y1 - 1997

N2 - In an attempt to prepare chiral discotic liquid crystals based on a helically twisted triphenylene nucleus a route has been developed for the introduction of a-fluoro, -chloro and -bromo substituents and it is shown that multiple a-halogenation is also possible. The monosubstituted derivatives all show enhanced mesophase stability whilst formation of the mesophase is suppressed for the polyhalogenated derivatives. Rather surprisingly, reaction of 2,3,6,7,10,11-hexahexyloxytriphenylene (HAT6) with iodine monochloride results in chlorination rather than iodination.

AB - In an attempt to prepare chiral discotic liquid crystals based on a helically twisted triphenylene nucleus a route has been developed for the introduction of a-fluoro, -chloro and -bromo substituents and it is shown that multiple a-halogenation is also possible. The monosubstituted derivatives all show enhanced mesophase stability whilst formation of the mesophase is suppressed for the polyhalogenated derivatives. Rather surprisingly, reaction of 2,3,6,7,10,11-hexahexyloxytriphenylene (HAT6) with iodine monochloride results in chlorination rather than iodination.

U2 - 10.1039/A606447G

DO - 10.1039/A606447G

M3 - Article

SN - 0959-9428

VL - 7

SP - 601

EP - 605

JO - Journal of Materials Chemistry

JF - Journal of Materials Chemistry

IS - 4

ER -