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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...

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Detalles Bibliográficos
Autores principales: de Jong, Jorn, Feringa, Ben L., Wezenberg, Sander J.
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/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.
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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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