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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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Detalles Bibliográficos
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
Descripción
Sumario: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.