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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...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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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. |
format | Online Article Text |
id | pubmed-9132087 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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