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Light‐Modulated Self‐Blockage of a Urea Binding Site in a Stiff‐Stilbene Based Anion Receptor
Anion binding to a receptor based on stiff‐stilbene, which is equipped with a urea hydrogen bond donating group and a phosphate or phosphinate hydrogen bond accepting group, can be controlled by light. In one photoaddressable state (E isomer) the urea binding site is available for binding, while in...
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/PMC6972635/ https://www.ncbi.nlm.nih.gov/pubmed/31622003 http://dx.doi.org/10.1002/cphc.201900917 |
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author | de Jong, Jorn Feringa, Ben L. Wezenberg, Sander J. |
author_facet | de Jong, Jorn Feringa, Ben L. Wezenberg, Sander J. |
author_sort | de Jong, Jorn |
collection | PubMed |
description | Anion binding to a receptor based on stiff‐stilbene, which is equipped with a urea hydrogen bond donating group and a phosphate or phosphinate hydrogen bond accepting group, can be controlled by light. In one photoaddressable state (E isomer) the urea binding site is available for binding, while in the other (Z isomer) it is blocked because of an intramolecular interaction with its hydrogen bond accepting motif. This intramolecular interaction is supported by DFT calculations and (1)H NMR titrations reveal a significantly lower anion binding strength for the state in which anion binding is blocked. Furthermore, the molecular switching process has been studied in detail by UV/Vis and NMR spectroscopy. The presented approach opens up new opportunities toward the development of photoresponsive anion receptors. |
format | Online Article Text |
id | pubmed-6972635 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-69726352020-01-27 Light‐Modulated Self‐Blockage of a Urea Binding Site in a Stiff‐Stilbene Based Anion Receptor de Jong, Jorn Feringa, Ben L. Wezenberg, Sander J. Chemphyschem Articles Anion binding to a receptor based on stiff‐stilbene, which is equipped with a urea hydrogen bond donating group and a phosphate or phosphinate hydrogen bond accepting group, can be controlled by light. In one photoaddressable state (E isomer) the urea binding site is available for binding, while in the other (Z isomer) it is blocked because of an intramolecular interaction with its hydrogen bond accepting motif. This intramolecular interaction is supported by DFT calculations and (1)H NMR titrations reveal a significantly lower anion binding strength for the state in which anion binding is blocked. Furthermore, the molecular switching process has been studied in detail by UV/Vis and NMR spectroscopy. The presented approach opens up new opportunities toward the development of photoresponsive anion receptors. John Wiley and Sons Inc. 2019-11-28 2019-12-16 /pmc/articles/PMC6972635/ /pubmed/31622003 http://dx.doi.org/10.1002/cphc.201900917 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 | Articles de Jong, Jorn Feringa, Ben L. Wezenberg, Sander J. Light‐Modulated Self‐Blockage of a Urea Binding Site in a Stiff‐Stilbene Based Anion Receptor |
title | Light‐Modulated Self‐Blockage of a Urea Binding Site in a Stiff‐Stilbene Based Anion Receptor |
title_full | Light‐Modulated Self‐Blockage of a Urea Binding Site in a Stiff‐Stilbene Based Anion Receptor |
title_fullStr | Light‐Modulated Self‐Blockage of a Urea Binding Site in a Stiff‐Stilbene Based Anion Receptor |
title_full_unstemmed | Light‐Modulated Self‐Blockage of a Urea Binding Site in a Stiff‐Stilbene Based Anion Receptor |
title_short | Light‐Modulated Self‐Blockage of a Urea Binding Site in a Stiff‐Stilbene Based Anion Receptor |
title_sort | light‐modulated self‐blockage of a urea binding site in a stiff‐stilbene based anion receptor |
topic | Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6972635/ https://www.ncbi.nlm.nih.gov/pubmed/31622003 http://dx.doi.org/10.1002/cphc.201900917 |
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