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Photomodulation of fluoride ion binding through anion-π interactions using a photoswitchable azobenzene system
The discovery of photoswitchable azobenzene-systems that undergo trans-to-cis photoisomerisation was a milestone in supramolecular chemistry. Such photoswitches have possible applications in data storage, stimuli responsive delivery systems, and molecular machines due to fast and selective switching...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4782172/ https://www.ncbi.nlm.nih.gov/pubmed/26953168 http://dx.doi.org/10.1038/srep22928 |
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author | Rananaware, Anushri Samanta, Mousumi Bhosale, Rajesh S. Kobaisi, Mohammad Al Roy, Biswajit Bheemireddy, Varun Bhosale, Sidhanath V. Bandyopadhyay, Subhajit Bhosale, Sheshanath V. |
author_facet | Rananaware, Anushri Samanta, Mousumi Bhosale, Rajesh S. Kobaisi, Mohammad Al Roy, Biswajit Bheemireddy, Varun Bhosale, Sidhanath V. Bandyopadhyay, Subhajit Bhosale, Sheshanath V. |
author_sort | Rananaware, Anushri |
collection | PubMed |
description | The discovery of photoswitchable azobenzene-systems that undergo trans-to-cis photoisomerisation was a milestone in supramolecular chemistry. Such photoswitches have possible applications in data storage, stimuli responsive delivery systems, and molecular machines due to fast and selective switching. However, the light induced cis isomer of azobenzene is rather unstable and reverts thermally and photochemically to the thermodynamically stable trans configuration. We report, for the first time, controlled photoswitching of an azo-naphthalenediimide (azo-NDI) which can be achieved upon binding of fluoride ions through anion-π interaction. This NDI-F–NDI “sandwich” stabilises the cis configuration through the generation of an NDI(•−) radical anion, and a dianionic, NDI(2−) species that becomes unusually stable in the cis form. The sandwiched cis form reverts to the trans form only upon decomplexation of F(−). A model pollutant was successfully degraded using the photogenerated NDI-F–NDI sandwich. This opens a wide range of applications in molecular and supramolecular nanotechnology. |
format | Online Article Text |
id | pubmed-4782172 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Nature Publishing Group |
record_format | MEDLINE/PubMed |
spelling | pubmed-47821722016-03-10 Photomodulation of fluoride ion binding through anion-π interactions using a photoswitchable azobenzene system Rananaware, Anushri Samanta, Mousumi Bhosale, Rajesh S. Kobaisi, Mohammad Al Roy, Biswajit Bheemireddy, Varun Bhosale, Sidhanath V. Bandyopadhyay, Subhajit Bhosale, Sheshanath V. Sci Rep Article The discovery of photoswitchable azobenzene-systems that undergo trans-to-cis photoisomerisation was a milestone in supramolecular chemistry. Such photoswitches have possible applications in data storage, stimuli responsive delivery systems, and molecular machines due to fast and selective switching. However, the light induced cis isomer of azobenzene is rather unstable and reverts thermally and photochemically to the thermodynamically stable trans configuration. We report, for the first time, controlled photoswitching of an azo-naphthalenediimide (azo-NDI) which can be achieved upon binding of fluoride ions through anion-π interaction. This NDI-F–NDI “sandwich” stabilises the cis configuration through the generation of an NDI(•−) radical anion, and a dianionic, NDI(2−) species that becomes unusually stable in the cis form. The sandwiched cis form reverts to the trans form only upon decomplexation of F(−). A model pollutant was successfully degraded using the photogenerated NDI-F–NDI sandwich. This opens a wide range of applications in molecular and supramolecular nanotechnology. Nature Publishing Group 2016-03-08 /pmc/articles/PMC4782172/ /pubmed/26953168 http://dx.doi.org/10.1038/srep22928 Text en Copyright © 2016, Macmillan Publishers Limited http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Article Rananaware, Anushri Samanta, Mousumi Bhosale, Rajesh S. Kobaisi, Mohammad Al Roy, Biswajit Bheemireddy, Varun Bhosale, Sidhanath V. Bandyopadhyay, Subhajit Bhosale, Sheshanath V. Photomodulation of fluoride ion binding through anion-π interactions using a photoswitchable azobenzene system |
title | Photomodulation of fluoride ion binding through anion-π interactions using a photoswitchable azobenzene system |
title_full | Photomodulation of fluoride ion binding through anion-π interactions using a photoswitchable azobenzene system |
title_fullStr | Photomodulation of fluoride ion binding through anion-π interactions using a photoswitchable azobenzene system |
title_full_unstemmed | Photomodulation of fluoride ion binding through anion-π interactions using a photoswitchable azobenzene system |
title_short | Photomodulation of fluoride ion binding through anion-π interactions using a photoswitchable azobenzene system |
title_sort | photomodulation of fluoride ion binding through anion-π interactions using a photoswitchable azobenzene system |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4782172/ https://www.ncbi.nlm.nih.gov/pubmed/26953168 http://dx.doi.org/10.1038/srep22928 |
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