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A new fluorescent chemosensor for fluoride anion based on a pyrrole-isoxazole derivative.

ABSTRACT: 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.

SUBMITTER: Yang Z

PROVIDER: S-EPMC3028564 | biostudies-literature | 2011 Jan

REPOSITORIES: biostudies-literature

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A new fluorescent chemosensor for fluoride anion based on a pyrrole-isoxazole derivative.

Yang Zhipei Z Zhang Kai K Gong Fangbin F Li Shayu S Chen Jun J Ma Jin Shi JS Sobenina Lyubov N LN Mikhaleva Albina I AI Yang Guoqiang G Trofimov Boris A BA

Beilstein journal of organic chemistry 20110112

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 f ...[more]

PMID: 21286394

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