Issue 24, 2017

Fluorescence light-up detection of cyanide in water based on cyclization reaction followed by ESIPT and AIEE

Abstract

Schiff base 1 (2,4-di-tert-butyl-6-((2-hydroxyphenyl-imino)-methyl)phenol) containing two hydroxyl groups could undergo an oxidative cyclization reaction and then generate hydroxyphenylbenzoxazole (HBO) 2 when CN was present as a catalyst. The multistep cyclization reaction was proved by spectroscopy, 1H NMR, 13C NMR and mass spectra. C[double bond, length as m-dash]N isomerization is the predominant decay process of the excited states, so sensor 1 is weakly emissive in solution at ambient temperature. When 1 reacts with CN, the emission is remarkably enhanced, where 1 is converted to 2. The cyclization product HBO 2 displays bright green luminescence in micellar due to the ESIPT (excited-state intramolecular proton transfer) as well as AIEE (aggregation-induced emission enhancement) effect. The detection limit is 5.92 × 10−7 M, lower than the WHO guideline of CN in drinking water (1.9 μM). The selective and competitive experiments reveal that sensor 1 shows high sensing selectivity and sensitivity for CN over other anions. Test papers containing absorbed 1 were prepared and applied for practical application of cyanide detection.

Graphical abstract: Fluorescence light-up detection of cyanide in water based on cyclization reaction followed by ESIPT and AIEE

Supplementary files

Article information

Article type
Paper
Submitted
06 Sep 2017
Accepted
08 Nov 2017
First published
27 Nov 2017

Analyst, 2017,142, 4825-4833

Fluorescence light-up detection of cyanide in water based on cyclization reaction followed by ESIPT and AIEE

C. Liang and S. Jiang, Analyst, 2017, 142, 4825 DOI: 10.1039/C7AN01479A

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