The synthesis of triphenylene-based discotic mesogens New and improved routes

Boden, N., Borner, R. C., Bushby, R. J., Cammidge, Andy ORCID: and Jesudason, M. V. (1993) The synthesis of triphenylene-based discotic mesogens New and improved routes. Liquid Crystals, 15 (6). pp. 851-858. ISSN 0267-8292

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The synthesis of discotic liquid crystal materials based on the triphenylene core normally involves the preparation of hexahydroxytriphenylene. This has traditionally been accomplished by a chloranil promoted trimerization of 1,2-dimethoxy-benzene followed by demethylation of the hexamethoxytriphenylene produced. Hexahydroxytriphenylene is subsequently alkylated to give the required derivative. The overall yield of this three step procedure is low and it is difficult to perform on a large scale. It is herein shown that a modified procedure using iron III chloride instead of chloranil yields hexa-alkoxytriphenylenes in a single step. The reaction is high yielding and can be performed on a large scale. This also provides a better route than those currently available for making the unsymmetrically substituted tri-phenylenes required in the synthesis of polymeric discotic liquid crystals. Some related elaborations of the triphenylene nucleus are also discussed.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Rachel Smith
Date Deposited: 08 Mar 2011 15:56
Last Modified: 15 Dec 2022 02:07
DOI: 10.1080/02678299308036504

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