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Multifunctional Benzothiadiazole-Based Small Molecules Displaying Solvatochromism and Sensing Properties toward Nitroarenes, Anions, and Cations**

Aryl or heteroaryl 5-substituted imidazo-benzothiadiazole derivatives were synthesized and shown to display remarkable solvatofluorochromism and selectively sense mercury(II) cations, acetate anions, and nitroaromatic derivatives, with discrimination between p-nitrophenol and picric acid. These nove...

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Autores principales: Alfonso, María, Espinosa, Arturo, Tárraga, Alberto, Molina, Pedro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Blackwell Publishing Ltd 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4280823/
https://www.ncbi.nlm.nih.gov/pubmed/25558442
http://dx.doi.org/10.1002/open.201402022
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author Alfonso, María
Espinosa, Arturo
Tárraga, Alberto
Molina, Pedro
author_facet Alfonso, María
Espinosa, Arturo
Tárraga, Alberto
Molina, Pedro
author_sort Alfonso, María
collection PubMed
description Aryl or heteroaryl 5-substituted imidazo-benzothiadiazole derivatives were synthesized and shown to display remarkable solvatofluorochromism and selectively sense mercury(II) cations, acetate anions, and nitroaromatic derivatives, with discrimination between p-nitrophenol and picric acid. These novel sensors are of importance these days, as the detection of explosives is a high priority in issues of national security and environmental protection. To determine the ion binding properties of the sensors, their absorption and fluorescence emission spectra upon binding different cations and anions were compared. Significant shifts in the spectra were only observed for mercury(II) and acetate. The binding of these two ions was further studied using (1)H NMR. The binding properties of different nitroaromatic compounds were also determined, and the results showed the importance of the presence of a phenol group in the guest molecule. Specifically, the two sensors were shown to discriminate between p-nitrophenol and picric acid. Finally, the mechanism of fluorescence quenching upon addition of nitrophenols was determined by computational methods.
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spelling pubmed-42808232015-01-02 Multifunctional Benzothiadiazole-Based Small Molecules Displaying Solvatochromism and Sensing Properties toward Nitroarenes, Anions, and Cations** Alfonso, María Espinosa, Arturo Tárraga, Alberto Molina, Pedro ChemistryOpen Full Papers Aryl or heteroaryl 5-substituted imidazo-benzothiadiazole derivatives were synthesized and shown to display remarkable solvatofluorochromism and selectively sense mercury(II) cations, acetate anions, and nitroaromatic derivatives, with discrimination between p-nitrophenol and picric acid. These novel sensors are of importance these days, as the detection of explosives is a high priority in issues of national security and environmental protection. To determine the ion binding properties of the sensors, their absorption and fluorescence emission spectra upon binding different cations and anions were compared. Significant shifts in the spectra were only observed for mercury(II) and acetate. The binding of these two ions was further studied using (1)H NMR. The binding properties of different nitroaromatic compounds were also determined, and the results showed the importance of the presence of a phenol group in the guest molecule. Specifically, the two sensors were shown to discriminate between p-nitrophenol and picric acid. Finally, the mechanism of fluorescence quenching upon addition of nitrophenols was determined by computational methods. Blackwell Publishing Ltd 2014-12 2014-09-26 /pmc/articles/PMC4280823/ /pubmed/25558442 http://dx.doi.org/10.1002/open.201402022 Text en © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. http://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs 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
Alfonso, María
Espinosa, Arturo
Tárraga, Alberto
Molina, Pedro
Multifunctional Benzothiadiazole-Based Small Molecules Displaying Solvatochromism and Sensing Properties toward Nitroarenes, Anions, and Cations**
title Multifunctional Benzothiadiazole-Based Small Molecules Displaying Solvatochromism and Sensing Properties toward Nitroarenes, Anions, and Cations**
title_full Multifunctional Benzothiadiazole-Based Small Molecules Displaying Solvatochromism and Sensing Properties toward Nitroarenes, Anions, and Cations**
title_fullStr Multifunctional Benzothiadiazole-Based Small Molecules Displaying Solvatochromism and Sensing Properties toward Nitroarenes, Anions, and Cations**
title_full_unstemmed Multifunctional Benzothiadiazole-Based Small Molecules Displaying Solvatochromism and Sensing Properties toward Nitroarenes, Anions, and Cations**
title_short Multifunctional Benzothiadiazole-Based Small Molecules Displaying Solvatochromism and Sensing Properties toward Nitroarenes, Anions, and Cations**
title_sort multifunctional benzothiadiazole-based small molecules displaying solvatochromism and sensing properties toward nitroarenes, anions, and cations**
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4280823/
https://www.ncbi.nlm.nih.gov/pubmed/25558442
http://dx.doi.org/10.1002/open.201402022
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