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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...

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Autores principales: Yang, Zhipei, Zhang, Kai, Gong, Fangbin, Li, Shayu, Chen, Jun, Ma, Jin Shi, Sobenina, Lyubov N, Mikhaleva, Albina I, Yang, Guoqiang, Trofimov, Boris A
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
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.
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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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