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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...

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Autores principales: Rananaware, Anushri, Samanta, Mousumi, Bhosale, Rajesh S., Kobaisi, Mohammad Al, Roy, Biswajit, Bheemireddy, Varun, Bhosale, Sidhanath V., Bandyopadhyay, Subhajit, Bhosale, Sheshanath V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2016
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.
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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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