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An Efficient Route to Stable Room‐Temperature Liquid‐Crystalline Triphenylenes
Author(s) -
Bock Harald,
Rajaoarivelo Mbolotiana,
Clavaguera Simon,
Grelet Éric
Publication year - 2006
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/ejoc.200600116
Subject(s) - chemistry , mesogen , discotic liquid crystal , alkyl , aqueous solution , self assembly , crystallography , liquid crystalline , chemical engineering , organic chemistry , polymer , molecule , engineering
Fourfold 2,3,6,10‐alkoxycarbonyl‐substituted triphenylenes are synthesised in five concise steps from 4‐methylcyclohexanone by selective monoformylation of 2,6,10‐trimethyltriphenylene, followed by oxidation in aqueous dichromate solution. Their low symmetry leads to mesogenic self assembly in a columnar liquid‐crystalline state at or near room temperature, depending on the choice of alkyl group. These materials unite several properties that are desirable in charge‐transporting thin films for organic optoelectronics: room‐temperature self assembly into structures of good charge mobility and high viscosity, low electron density in the aromatic core, smooth synthetic access, and optical transparency. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)