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A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative
Molecules containing polarized NH fragments that behave as anion-binding motifs are widely used as receptors for recognition and sensing purposes in aprotic solvents. We present here a new example of a receptor, 3-amino-5-(4,5,6,7-tetrahydro-1H-indol-2-yl)isoxazole-4-carboxamide (receptor 1), which...
Autores principales: | , , , , , , , , , |
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Formato: | Texto |
Lenguaje: | English |
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Beilstein-Institut
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3028564/ https://www.ncbi.nlm.nih.gov/pubmed/21286394 http://dx.doi.org/10.3762/bjoc.7.8 |
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author | Yang, Zhipei Zhang, Kai Gong, Fangbin Li, Shayu Chen, Jun Ma, Jin Shi Sobenina, Lyubov N Mikhaleva, Albina I Yang, Guoqiang Trofimov, Boris A |
author_facet | Yang, Zhipei Zhang, Kai Gong, Fangbin Li, Shayu Chen, Jun Ma, Jin Shi Sobenina, Lyubov N Mikhaleva, Albina I Yang, Guoqiang Trofimov, Boris A |
author_sort | Yang, Zhipei |
collection | PubMed |
description | Molecules containing polarized NH fragments that behave as anion-binding motifs are widely used as receptors for recognition and sensing purposes in aprotic solvents. We present here a new example of a receptor, 3-amino-5-(4,5,6,7-tetrahydro-1H-indol-2-yl)isoxazole-4-carboxamide (receptor 1), which contains pyrrole, amide and amino subunits. This receptor shows both changes in its UV–vis absorption and fluorescence emission spectra upon the addition of F(−), resulting in highly selectivity for fluoride detection over other anions, such as Cl(−), Br(−), I(−), HSO(4)(−), H(2)PO(4)(−) and AcO(−) in CH(3)CN. (1)H NMR titration, time-dependent density functional theory (TDDFT) calculations and other experiments confirm that the sensing process is brought about by deprotonation of the pyrrole-NH in receptor 1. |
format | Text |
id | pubmed-3028564 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-30285642011-01-31 A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative Yang, Zhipei Zhang, Kai Gong, Fangbin Li, Shayu Chen, Jun Ma, Jin Shi Sobenina, Lyubov N Mikhaleva, Albina I Yang, Guoqiang Trofimov, Boris A Beilstein J Org Chem Full Research Paper Molecules containing polarized NH fragments that behave as anion-binding motifs are widely used as receptors for recognition and sensing purposes in aprotic solvents. We present here a new example of a receptor, 3-amino-5-(4,5,6,7-tetrahydro-1H-indol-2-yl)isoxazole-4-carboxamide (receptor 1), which contains pyrrole, amide and amino subunits. This receptor shows both changes in its UV–vis absorption and fluorescence emission spectra upon the addition of F(−), resulting in highly selectivity for fluoride detection over other anions, such as Cl(−), Br(−), I(−), HSO(4)(−), H(2)PO(4)(−) and AcO(−) in CH(3)CN. (1)H NMR titration, time-dependent density functional theory (TDDFT) calculations and other experiments confirm that the sensing process is brought about by deprotonation of the pyrrole-NH in receptor 1. Beilstein-Institut 2011-01-12 /pmc/articles/PMC3028564/ /pubmed/21286394 http://dx.doi.org/10.3762/bjoc.7.8 Text en Copyright © 2011, Yang et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Yang, Zhipei Zhang, Kai Gong, Fangbin Li, Shayu Chen, Jun Ma, Jin Shi Sobenina, Lyubov N Mikhaleva, Albina I Yang, Guoqiang Trofimov, Boris A A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative |
title | A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative |
title_full | A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative |
title_fullStr | A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative |
title_full_unstemmed | A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative |
title_short | A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative |
title_sort | new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3028564/ https://www.ncbi.nlm.nih.gov/pubmed/21286394 http://dx.doi.org/10.3762/bjoc.7.8 |
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