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Light‐Responsive Arylazopyrazole Gelators: From Organic to Aqueous Media and from Supramolecular to Dynamic Covalent Chemistry
Versatile photoresponsive gels based on tripodal low molecular weight gelators (LMWGs) are reported. A cyclohexane‐1,3,5‐tricarboxamide (CTA) core provides face‐to‐face hydrogen bonding and a planar conformation, inducing the self‐assembly of supramolecular polymers. The CTA core was substituted wit...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6593461/ https://www.ncbi.nlm.nih.gov/pubmed/30791165 http://dx.doi.org/10.1002/chem.201806042 |
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author | Chu, Chih‐Wei Stricker, Lucas Kirse, Thomas M. Hayduk, Matthias Ravoo, Bart Jan |
author_facet | Chu, Chih‐Wei Stricker, Lucas Kirse, Thomas M. Hayduk, Matthias Ravoo, Bart Jan |
author_sort | Chu, Chih‐Wei |
collection | PubMed |
description | Versatile photoresponsive gels based on tripodal low molecular weight gelators (LMWGs) are reported. A cyclohexane‐1,3,5‐tricarboxamide (CTA) core provides face‐to‐face hydrogen bonding and a planar conformation, inducing the self‐assembly of supramolecular polymers. The CTA core was substituted with three arylazopyrazole (AAP) arms. AAP is a molecular photoswitch that isomerizes reversibly under alternating UV and green light irradiation. The E isomer of AAP is planar, favoring the self‐assembly, whereas the Z isomer has a twisted structure, leading to a disassembly of the supramolecular polymers. By using tailor‐made molecular design of the tripodal gelator, light‐responsive organogels and hydrogels were obtained. Additionally, in the case of the hydrogels, AAP was coupled to the core through hydrazones, so that the hydrogelator and, hence, the photoresponsive hydrogel could also be assembled and disassembled by using dynamic covalent chemistry. |
format | Online Article Text |
id | pubmed-6593461 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-65934612019-07-10 Light‐Responsive Arylazopyrazole Gelators: From Organic to Aqueous Media and from Supramolecular to Dynamic Covalent Chemistry Chu, Chih‐Wei Stricker, Lucas Kirse, Thomas M. Hayduk, Matthias Ravoo, Bart Jan Chemistry Full Papers Versatile photoresponsive gels based on tripodal low molecular weight gelators (LMWGs) are reported. A cyclohexane‐1,3,5‐tricarboxamide (CTA) core provides face‐to‐face hydrogen bonding and a planar conformation, inducing the self‐assembly of supramolecular polymers. The CTA core was substituted with three arylazopyrazole (AAP) arms. AAP is a molecular photoswitch that isomerizes reversibly under alternating UV and green light irradiation. The E isomer of AAP is planar, favoring the self‐assembly, whereas the Z isomer has a twisted structure, leading to a disassembly of the supramolecular polymers. By using tailor‐made molecular design of the tripodal gelator, light‐responsive organogels and hydrogels were obtained. Additionally, in the case of the hydrogels, AAP was coupled to the core through hydrazones, so that the hydrogelator and, hence, the photoresponsive hydrogel could also be assembled and disassembled by using dynamic covalent chemistry. John Wiley and Sons Inc. 2019-03-27 2019-04-26 /pmc/articles/PMC6593461/ /pubmed/30791165 http://dx.doi.org/10.1002/chem.201806042 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Full Papers Chu, Chih‐Wei Stricker, Lucas Kirse, Thomas M. Hayduk, Matthias Ravoo, Bart Jan Light‐Responsive Arylazopyrazole Gelators: From Organic to Aqueous Media and from Supramolecular to Dynamic Covalent Chemistry |
title | Light‐Responsive Arylazopyrazole Gelators: From Organic to Aqueous Media and from Supramolecular to Dynamic Covalent Chemistry |
title_full | Light‐Responsive Arylazopyrazole Gelators: From Organic to Aqueous Media and from Supramolecular to Dynamic Covalent Chemistry |
title_fullStr | Light‐Responsive Arylazopyrazole Gelators: From Organic to Aqueous Media and from Supramolecular to Dynamic Covalent Chemistry |
title_full_unstemmed | Light‐Responsive Arylazopyrazole Gelators: From Organic to Aqueous Media and from Supramolecular to Dynamic Covalent Chemistry |
title_short | Light‐Responsive Arylazopyrazole Gelators: From Organic to Aqueous Media and from Supramolecular to Dynamic Covalent Chemistry |
title_sort | light‐responsive arylazopyrazole gelators: from organic to aqueous media and from supramolecular to dynamic covalent chemistry |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6593461/ https://www.ncbi.nlm.nih.gov/pubmed/30791165 http://dx.doi.org/10.1002/chem.201806042 |
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