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Chiral Self-Sorting and the Realization of Ferroelectricity in the Columnar Liquid Crystal Phase of an Optically Inactive N,N′-Diphenylurea Derivative Possessing Six (±)-Citronellyl Groups

[Image: see text] An axially polar-ferroelectric columnar liquid crystal (AP-FCLC) phase that exhibits both switching and maintenance of the macro-polarity in the column axis direction has been achieved in an N,N′-bis(3,4,5-trialkoxyphenyl)urea compound (rac-1) prepared from (±)-citronellyl bromide....

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Autores principales: Moriya, Miyu, Kohri, Michinari, Kishikawa, Keiki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8296585/
https://www.ncbi.nlm.nih.gov/pubmed/34308076
http://dx.doi.org/10.1021/acsomega.1c02534
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author Moriya, Miyu
Kohri, Michinari
Kishikawa, Keiki
author_facet Moriya, Miyu
Kohri, Michinari
Kishikawa, Keiki
author_sort Moriya, Miyu
collection PubMed
description [Image: see text] An axially polar-ferroelectric columnar liquid crystal (AP-FCLC) phase that exhibits both switching and maintenance of the macro-polarity in the column axis direction has been achieved in an N,N′-bis(3,4,5-trialkoxyphenyl)urea compound (rac-1) prepared from (±)-citronellyl bromide. Although it had been thought that chirality is necessary to achieve the AP-FCLC phase from our previous study, the optically inactive compound which is a mixture of 21 stereoisomers, generated an AP-FCLC phase. We confirmed its ferroelectricity and investigated the mechanism for realizing the AP-FCLC phase using optoelectronic experiments, X-ray diffraction, and circular dichroism spectroscopy. As a result, it was suggested that chiral self-sorting occurs in the columnar liquid crystal phase, in which molecules with a similar stereochemistry form a one-handed helical column, and columns with the same helicity gather together to form a chiral domain. Accordingly, we conclude that the optically inactive compound rac-1 also indicates ferroelectricity similar to that of an optically pure urea compound because of chiral self-sorting.
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spelling pubmed-82965852021-07-23 Chiral Self-Sorting and the Realization of Ferroelectricity in the Columnar Liquid Crystal Phase of an Optically Inactive N,N′-Diphenylurea Derivative Possessing Six (±)-Citronellyl Groups Moriya, Miyu Kohri, Michinari Kishikawa, Keiki ACS Omega [Image: see text] An axially polar-ferroelectric columnar liquid crystal (AP-FCLC) phase that exhibits both switching and maintenance of the macro-polarity in the column axis direction has been achieved in an N,N′-bis(3,4,5-trialkoxyphenyl)urea compound (rac-1) prepared from (±)-citronellyl bromide. Although it had been thought that chirality is necessary to achieve the AP-FCLC phase from our previous study, the optically inactive compound which is a mixture of 21 stereoisomers, generated an AP-FCLC phase. We confirmed its ferroelectricity and investigated the mechanism for realizing the AP-FCLC phase using optoelectronic experiments, X-ray diffraction, and circular dichroism spectroscopy. As a result, it was suggested that chiral self-sorting occurs in the columnar liquid crystal phase, in which molecules with a similar stereochemistry form a one-handed helical column, and columns with the same helicity gather together to form a chiral domain. Accordingly, we conclude that the optically inactive compound rac-1 also indicates ferroelectricity similar to that of an optically pure urea compound because of chiral self-sorting. American Chemical Society 2021-07-10 /pmc/articles/PMC8296585/ /pubmed/34308076 http://dx.doi.org/10.1021/acsomega.1c02534 Text en © 2021 The Authors. Published by American Chemical Society Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Moriya, Miyu
Kohri, Michinari
Kishikawa, Keiki
Chiral Self-Sorting and the Realization of Ferroelectricity in the Columnar Liquid Crystal Phase of an Optically Inactive N,N′-Diphenylurea Derivative Possessing Six (±)-Citronellyl Groups
title Chiral Self-Sorting and the Realization of Ferroelectricity in the Columnar Liquid Crystal Phase of an Optically Inactive N,N′-Diphenylurea Derivative Possessing Six (±)-Citronellyl Groups
title_full Chiral Self-Sorting and the Realization of Ferroelectricity in the Columnar Liquid Crystal Phase of an Optically Inactive N,N′-Diphenylurea Derivative Possessing Six (±)-Citronellyl Groups
title_fullStr Chiral Self-Sorting and the Realization of Ferroelectricity in the Columnar Liquid Crystal Phase of an Optically Inactive N,N′-Diphenylurea Derivative Possessing Six (±)-Citronellyl Groups
title_full_unstemmed Chiral Self-Sorting and the Realization of Ferroelectricity in the Columnar Liquid Crystal Phase of an Optically Inactive N,N′-Diphenylurea Derivative Possessing Six (±)-Citronellyl Groups
title_short Chiral Self-Sorting and the Realization of Ferroelectricity in the Columnar Liquid Crystal Phase of an Optically Inactive N,N′-Diphenylurea Derivative Possessing Six (±)-Citronellyl Groups
title_sort chiral self-sorting and the realization of ferroelectricity in the columnar liquid crystal phase of an optically inactive n,n′-diphenylurea derivative possessing six (±)-citronellyl groups
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8296585/
https://www.ncbi.nlm.nih.gov/pubmed/34308076
http://dx.doi.org/10.1021/acsomega.1c02534
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