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Easily Accessible Thermotropic Hydrogen‐Bonded Columnar Discotic Liquid Crystals from Fatty Acid– Tris‐Benzoimidazolyl Benzene Complexes

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 d...

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Autores principales: Lugger, Jody A. M., Sijbesma, Rint P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5167330/
https://www.ncbi.nlm.nih.gov/pubmed/28032028
http://dx.doi.org/10.1002/open.201600078
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author Lugger, Jody A. M.
Sijbesma, Rint P.
author_facet Lugger, Jody A. M.
Sijbesma, Rint P.
author_sort Lugger, Jody A. M.
collection PubMed
description 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.
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spelling pubmed-51673302016-12-28 Easily Accessible Thermotropic Hydrogen‐Bonded Columnar Discotic Liquid Crystals from Fatty Acid– Tris‐Benzoimidazolyl Benzene Complexes Lugger, Jody A. M. Sijbesma, Rint P. ChemistryOpen Full Papers 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. John Wiley and Sons Inc. 2016-10-24 /pmc/articles/PMC5167330/ /pubmed/28032028 http://dx.doi.org/10.1002/open.201600078 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Lugger, Jody A. M.
Sijbesma, Rint P.
Easily Accessible Thermotropic Hydrogen‐Bonded Columnar Discotic Liquid Crystals from Fatty Acid– Tris‐Benzoimidazolyl Benzene Complexes
title Easily Accessible Thermotropic Hydrogen‐Bonded Columnar Discotic Liquid Crystals from Fatty Acid– Tris‐Benzoimidazolyl Benzene Complexes
title_full Easily Accessible Thermotropic Hydrogen‐Bonded Columnar Discotic Liquid Crystals from Fatty Acid– Tris‐Benzoimidazolyl Benzene Complexes
title_fullStr Easily Accessible Thermotropic Hydrogen‐Bonded Columnar Discotic Liquid Crystals from Fatty Acid– Tris‐Benzoimidazolyl Benzene Complexes
title_full_unstemmed Easily Accessible Thermotropic Hydrogen‐Bonded Columnar Discotic Liquid Crystals from Fatty Acid– Tris‐Benzoimidazolyl Benzene Complexes
title_short Easily Accessible Thermotropic Hydrogen‐Bonded Columnar Discotic Liquid Crystals from Fatty Acid– Tris‐Benzoimidazolyl Benzene Complexes
title_sort easily accessible thermotropic hydrogen‐bonded columnar discotic liquid crystals from fatty acid– tris‐benzoimidazolyl benzene complexes
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5167330/
https://www.ncbi.nlm.nih.gov/pubmed/28032028
http://dx.doi.org/10.1002/open.201600078
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