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Substituent effects of bridged binaphthyl-type chiral dopants on the helical twisting power in dopant-induced chiral liquid crystals

A new series of chiral dopants, (R)-6,6′-halogenated (1b–1e, X = F, Cl, Br and I) and -methylated (1f) binaphthyl compounds, were designed and synthesized to create chiral liquid crystals by doping them into an achiral nematic liquid crystal (NLC). The influence of halogen (X = F, Cl, Br and I) and...

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Autores principales: Narazaki, Yu, Nishikawa, Hiroya, Higuchi, Hiroki, Okumura, Yasushi, Kikuchi, Hirotsugu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9077017/
https://www.ncbi.nlm.nih.gov/pubmed/35538948
http://dx.doi.org/10.1039/c7ra12465a
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author Narazaki, Yu
Nishikawa, Hiroya
Higuchi, Hiroki
Okumura, Yasushi
Kikuchi, Hirotsugu
author_facet Narazaki, Yu
Nishikawa, Hiroya
Higuchi, Hiroki
Okumura, Yasushi
Kikuchi, Hirotsugu
author_sort Narazaki, Yu
collection PubMed
description A new series of chiral dopants, (R)-6,6′-halogenated (1b–1e, X = F, Cl, Br and I) and -methylated (1f) binaphthyl compounds, were designed and synthesized to create chiral liquid crystals by doping them into an achiral nematic liquid crystal (NLC). The influence of halogen (X = F, Cl, Br and I) and methyl substituent factors, such as steric, polar, and polarizability properties, on the helical twisting power (HTP) and their temperature dependences on the chiral dopants were investigated in two host NLCs with different characteristics, fluorinated JC-1041XX and N-(4-methoxybenzylidene)-4-butylaniline (MBBA). The chiral dopants possessing less steric and larger polarizability factors increased the HTP values. The structural similarity and electrostatic arene–arene interactions between the chiral dopants and the NLC molecules also exerted important influences on these values. The temperature dependence of the HTP (HTP(t.d.)) values also correlated well with the steric and polarizability substituents factors in the two host NLCs. Their correlation coefficients (R(2)) depended on the molecular structural similarity between the chiral dopant and the NLC.
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spelling pubmed-90770172022-05-09 Substituent effects of bridged binaphthyl-type chiral dopants on the helical twisting power in dopant-induced chiral liquid crystals Narazaki, Yu Nishikawa, Hiroya Higuchi, Hiroki Okumura, Yasushi Kikuchi, Hirotsugu RSC Adv Chemistry A new series of chiral dopants, (R)-6,6′-halogenated (1b–1e, X = F, Cl, Br and I) and -methylated (1f) binaphthyl compounds, were designed and synthesized to create chiral liquid crystals by doping them into an achiral nematic liquid crystal (NLC). The influence of halogen (X = F, Cl, Br and I) and methyl substituent factors, such as steric, polar, and polarizability properties, on the helical twisting power (HTP) and their temperature dependences on the chiral dopants were investigated in two host NLCs with different characteristics, fluorinated JC-1041XX and N-(4-methoxybenzylidene)-4-butylaniline (MBBA). The chiral dopants possessing less steric and larger polarizability factors increased the HTP values. The structural similarity and electrostatic arene–arene interactions between the chiral dopants and the NLC molecules also exerted important influences on these values. The temperature dependence of the HTP (HTP(t.d.)) values also correlated well with the steric and polarizability substituents factors in the two host NLCs. Their correlation coefficients (R(2)) depended on the molecular structural similarity between the chiral dopant and the NLC. The Royal Society of Chemistry 2018-01-03 /pmc/articles/PMC9077017/ /pubmed/35538948 http://dx.doi.org/10.1039/c7ra12465a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Narazaki, Yu
Nishikawa, Hiroya
Higuchi, Hiroki
Okumura, Yasushi
Kikuchi, Hirotsugu
Substituent effects of bridged binaphthyl-type chiral dopants on the helical twisting power in dopant-induced chiral liquid crystals
title Substituent effects of bridged binaphthyl-type chiral dopants on the helical twisting power in dopant-induced chiral liquid crystals
title_full Substituent effects of bridged binaphthyl-type chiral dopants on the helical twisting power in dopant-induced chiral liquid crystals
title_fullStr Substituent effects of bridged binaphthyl-type chiral dopants on the helical twisting power in dopant-induced chiral liquid crystals
title_full_unstemmed Substituent effects of bridged binaphthyl-type chiral dopants on the helical twisting power in dopant-induced chiral liquid crystals
title_short Substituent effects of bridged binaphthyl-type chiral dopants on the helical twisting power in dopant-induced chiral liquid crystals
title_sort substituent effects of bridged binaphthyl-type chiral dopants on the helical twisting power in dopant-induced chiral liquid crystals
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9077017/
https://www.ncbi.nlm.nih.gov/pubmed/35538948
http://dx.doi.org/10.1039/c7ra12465a
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