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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....
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2021
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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. |
format | Online Article Text |
id | pubmed-8296585 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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