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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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2011-01, Vol.7 (1), p.46-52
Main Authors: Yang, Zhipei, Zhang, Kai, Gong, Fangbin, Li, Shayu, Chen, Jun, Ma, Jin Shi, Sobenina, Lyubov N, Mikhaleva, Albina I, Yang, Guoqiang, Trofimov, Boris A
Format: Article
Language:English
Subjects:
Chemistry
deprotonation
fluorescent chemosensor
fluoride anion recognition
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Summary: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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.7.8