Open AccessEasily Accessible Thermotropic Hydrogen‐Bonded Columnar Discotic Liquid Crystals from Fatty Acid– Tris‐Benzoimidazolyl Benzene Complexes
Author(s) -
Lugger Jody A. M.,
Sijbesma Rint P.
Publication year - 2016
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201600078
Subject(s) - mesophase , hydrogen bond , organic chemistry , thermotropic crystal , chemistry , polymer chemistry , polymer , liquid crystal , phase (matter) , materials science , molecule , liquid crystalline , optoelectronics
We report the formation of easily accessible hydrogen‐bonded columnar discotic liquid crystals (LCs) based on tris‐benzoimidazolyl benzene ( TBIB ) and commercially available fatty acids. By increasing the length of the fatty acid, the temperature range of liquid crystallinity was tuned. Introducing double bonds in octadecanoic acid lowered the crystallization temperature and increased the temperature range of the mesophase. Surprisingly, dimerized linoleic acid also forms an LC phase. When using branched aliphatic acids with the branching point close to the acid moiety, the mesophase was lost, whereas phosphonic acid or benzenesulfonic acid derivatives did have a mesophase, showing that the generality of this approach extends beyond carboxylic acids as the hydrogen‐bond donor. Furthermore, a polymerizable LC phase was obtained from mixtures of TBIB with a methacrylate‐bearing fatty acid, providing an approach for the fabrication of nanoporous polymer films if the methacrylate groups are polymerized. Finally, the higher solubility of methyl‐ TBIB was used to suppress phase separation in stoichiometric mixtures of the template molecule with fatty acids.