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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...

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Autores principales: Chu, Chih‐Wei, Stricker, Lucas, Kirse, Thomas M., Hayduk, Matthias, Ravoo, Bart Jan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
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.
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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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