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CPL on/off control of an assembled system by water soluble macrocyclic chiral sources with planar chirality

Herein, we report the synthesis and planar chiral properties of a pair of water-soluble cationic pillar[5]arenes with stereogenic carbons. Interestingly, although units of the molecules were rotatable, only one planar chiral diastereomer existed in water in both cases. As a new type of chiral source...

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Autores principales: Fa, Shixin, Tomita, Takuya, Wada, Keisuke, Yasuhara, Kazuma, Ohtani, Shunsuke, Kato, Kenichi, Gon, Masayuki, Tanaka, Kazuo, Kakuta, Takahiro, Yamagishi, Tada-aki, Ogoshi, Tomoki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9132087/
https://www.ncbi.nlm.nih.gov/pubmed/35685810
http://dx.doi.org/10.1039/d2sc00952h
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author Fa, Shixin
Tomita, Takuya
Wada, Keisuke
Yasuhara, Kazuma
Ohtani, Shunsuke
Kato, Kenichi
Gon, Masayuki
Tanaka, Kazuo
Kakuta, Takahiro
Yamagishi, Tada-aki
Ogoshi, Tomoki
author_facet Fa, Shixin
Tomita, Takuya
Wada, Keisuke
Yasuhara, Kazuma
Ohtani, Shunsuke
Kato, Kenichi
Gon, Masayuki
Tanaka, Kazuo
Kakuta, Takahiro
Yamagishi, Tada-aki
Ogoshi, Tomoki
author_sort Fa, Shixin
collection PubMed
description Herein, we report the synthesis and planar chiral properties of a pair of water-soluble cationic pillar[5]arenes with stereogenic carbons. Interestingly, although units of the molecules were rotatable, only one planar chiral diastereomer existed in water in both cases. As a new type of chiral source, these molecules transmitted chiral information from the planar chiral cavities to the assembly of a water-soluble extended π-conjugated compound, affording circularly polarized luminescence (CPL). The chirality transfer process and resulting CPL were extremely sensitive to the feed ratio of the chiral pillar[5]arenes owing to the combined action of their planar chirality, bulkiness, and strong binding properties. When a limited amount of chiral source was added, further assembly of the extended π-conjugated compound into helical fibers with CPL was triggered. Unexpectedly, larger amounts of chiral source destroyed the helical fiber assemblies, resulting in elimination of the chirality and CPL properties from the assembled structures.
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spelling pubmed-91320872022-06-08 CPL on/off control of an assembled system by water soluble macrocyclic chiral sources with planar chirality Fa, Shixin Tomita, Takuya Wada, Keisuke Yasuhara, Kazuma Ohtani, Shunsuke Kato, Kenichi Gon, Masayuki Tanaka, Kazuo Kakuta, Takahiro Yamagishi, Tada-aki Ogoshi, Tomoki Chem Sci Chemistry Herein, we report the synthesis and planar chiral properties of a pair of water-soluble cationic pillar[5]arenes with stereogenic carbons. Interestingly, although units of the molecules were rotatable, only one planar chiral diastereomer existed in water in both cases. As a new type of chiral source, these molecules transmitted chiral information from the planar chiral cavities to the assembly of a water-soluble extended π-conjugated compound, affording circularly polarized luminescence (CPL). The chirality transfer process and resulting CPL were extremely sensitive to the feed ratio of the chiral pillar[5]arenes owing to the combined action of their planar chirality, bulkiness, and strong binding properties. When a limited amount of chiral source was added, further assembly of the extended π-conjugated compound into helical fibers with CPL was triggered. Unexpectedly, larger amounts of chiral source destroyed the helical fiber assemblies, resulting in elimination of the chirality and CPL properties from the assembled structures. The Royal Society of Chemistry 2022-03-30 /pmc/articles/PMC9132087/ /pubmed/35685810 http://dx.doi.org/10.1039/d2sc00952h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Fa, Shixin
Tomita, Takuya
Wada, Keisuke
Yasuhara, Kazuma
Ohtani, Shunsuke
Kato, Kenichi
Gon, Masayuki
Tanaka, Kazuo
Kakuta, Takahiro
Yamagishi, Tada-aki
Ogoshi, Tomoki
CPL on/off control of an assembled system by water soluble macrocyclic chiral sources with planar chirality
title CPL on/off control of an assembled system by water soluble macrocyclic chiral sources with planar chirality
title_full CPL on/off control of an assembled system by water soluble macrocyclic chiral sources with planar chirality
title_fullStr CPL on/off control of an assembled system by water soluble macrocyclic chiral sources with planar chirality
title_full_unstemmed CPL on/off control of an assembled system by water soluble macrocyclic chiral sources with planar chirality
title_short CPL on/off control of an assembled system by water soluble macrocyclic chiral sources with planar chirality
title_sort cpl on/off control of an assembled system by water soluble macrocyclic chiral sources with planar chirality
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9132087/
https://www.ncbi.nlm.nih.gov/pubmed/35685810
http://dx.doi.org/10.1039/d2sc00952h
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