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Gram-scale preparation of negative-type liquid crystals with a CF(2)CF(2)-carbocycle unit via an improved short-step synthetic protocol
Herein, we demonstrate an improved short-step protocol for the synthesis of multicyclic molecules having a CF(2)CF(2)-containing cyclohexadiene or cyclohexane framework in a mesogenic structure. These molecules are promising candidates for vertical alignment (VA)-mode liquid crystal (LC) display dev...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5789429/ https://www.ncbi.nlm.nih.gov/pubmed/29441138 http://dx.doi.org/10.3762/bjoc.14.10 |
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author | Kumon, Tatsuya Hashishita, Shohei Kida, Takumi Yamada, Shigeyuki Ishihara, Takashi Konno, Tsutomu |
author_facet | Kumon, Tatsuya Hashishita, Shohei Kida, Takumi Yamada, Shigeyuki Ishihara, Takashi Konno, Tsutomu |
author_sort | Kumon, Tatsuya |
collection | PubMed |
description | Herein, we demonstrate an improved short-step protocol for the synthesis of multicyclic molecules having a CF(2)CF(2)-containing cyclohexadiene or cyclohexane framework in a mesogenic structure. These molecules are promising candidates for vertical alignment (VA)-mode liquid crystal (LC) display devices owing to their large negative dielectric constant. The tetrafluorinated multicyclic molecules were successfully obtained in only five or six reaction steps without the need for special handling techniques, as is generally required for thermally unstable organometallic species, representing a reduction of three reaction steps. The improved short-step synthetic protocol was also amenable to the multigram preparation of these promising molecules, which may contribute significantly to the development of novel negative-type LC molecules containing CF(2)CF(2) carbocycles. |
format | Online Article Text |
id | pubmed-5789429 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-57894292018-02-13 Gram-scale preparation of negative-type liquid crystals with a CF(2)CF(2)-carbocycle unit via an improved short-step synthetic protocol Kumon, Tatsuya Hashishita, Shohei Kida, Takumi Yamada, Shigeyuki Ishihara, Takashi Konno, Tsutomu Beilstein J Org Chem Full Research Paper Herein, we demonstrate an improved short-step protocol for the synthesis of multicyclic molecules having a CF(2)CF(2)-containing cyclohexadiene or cyclohexane framework in a mesogenic structure. These molecules are promising candidates for vertical alignment (VA)-mode liquid crystal (LC) display devices owing to their large negative dielectric constant. The tetrafluorinated multicyclic molecules were successfully obtained in only five or six reaction steps without the need for special handling techniques, as is generally required for thermally unstable organometallic species, representing a reduction of three reaction steps. The improved short-step synthetic protocol was also amenable to the multigram preparation of these promising molecules, which may contribute significantly to the development of novel negative-type LC molecules containing CF(2)CF(2) carbocycles. Beilstein-Institut 2018-01-15 /pmc/articles/PMC5789429/ /pubmed/29441138 http://dx.doi.org/10.3762/bjoc.14.10 Text en Copyright © 2018, Kumon et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Kumon, Tatsuya Hashishita, Shohei Kida, Takumi Yamada, Shigeyuki Ishihara, Takashi Konno, Tsutomu Gram-scale preparation of negative-type liquid crystals with a CF(2)CF(2)-carbocycle unit via an improved short-step synthetic protocol |
title | Gram-scale preparation of negative-type liquid crystals with a CF(2)CF(2)-carbocycle unit via an improved short-step synthetic protocol |
title_full | Gram-scale preparation of negative-type liquid crystals with a CF(2)CF(2)-carbocycle unit via an improved short-step synthetic protocol |
title_fullStr | Gram-scale preparation of negative-type liquid crystals with a CF(2)CF(2)-carbocycle unit via an improved short-step synthetic protocol |
title_full_unstemmed | Gram-scale preparation of negative-type liquid crystals with a CF(2)CF(2)-carbocycle unit via an improved short-step synthetic protocol |
title_short | Gram-scale preparation of negative-type liquid crystals with a CF(2)CF(2)-carbocycle unit via an improved short-step synthetic protocol |
title_sort | gram-scale preparation of negative-type liquid crystals with a cf(2)cf(2)-carbocycle unit via an improved short-step synthetic protocol |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5789429/ https://www.ncbi.nlm.nih.gov/pubmed/29441138 http://dx.doi.org/10.3762/bjoc.14.10 |
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