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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...

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Autores principales: Kumon, Tatsuya, Hashishita, Shohei, Kida, Takumi, Yamada, Shigeyuki, Ishihara, Takashi, Konno, Tsutomu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
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.
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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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