Optimizing the electron-withdrawing character on benzenesulfonyl moiety attached to a glyco-conjugate to impart sensitive and selective sensing of cyanide in HEPES buffer and on cellulose paper and silica gel strips

Areti, Sivaiah ; Bandaru, Sateesh ; Yarramala, Deepthi S. ; Rao, Chebrolu Pulla (2015) Optimizing the electron-withdrawing character on benzenesulfonyl moiety attached to a glyco-conjugate to impart sensitive and selective sensing of cyanide in HEPES buffer and on cellulose paper and silica gel strips Analytical Chemistry, 87 (24). pp. 12396-12403. ISSN 0003-2700

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Official URL: http://pubs.acs.org/doi/abs/10.1021/acs.analchem.5...

Related URL: http://dx.doi.org/10.1021/acs.analchem.5b04085

Abstract

Dansyl-derivatized, triazole-linked, glucopyranosyl conjugates, 5FLOH, 2FLOH, 1FLOH, and 0FLOH were synthesized and characterized. While the 5FLOH acts as a molecular probe for CN, 2FLOH, 1FLOH, and 0FLOH acts as control molecules. The reactivity of CN toward 5FLOH has been elicited through the changes observed in NMR, ESI MS, emission, and absorption spectroscopy. The conjugate 5FLOH releases a fluorescent product upon reaction by CN in aqueous acetonitrile medium by exhibiting an ∼125-fold fluorescence enhancement even in the presence of other anions. Fluorescence switch-on behavior has been clearly demonstrated on the basis of the nucleophilic substitution reaction of CN on 5FLOH. A minimum detection limit of (2.3 ± 0.3) × 10–7 M (6 ± 1 ppb) was shown by 5FLOH for CN in solution. All the other anions studied showed no change in the fluorescence emission. The utility of 5FLOH has been demonstrated by showing its reactivity toward CN on a thin layer of silica gel as well as on Whatman No. 1 cellulose filter paper strips. The role of glucose moiety and the penta-fluorobenzenesulfonyl reactive center present in 5FLOH in the selectivity of CN over other anions has been demonstrated by fluorescence, absorption and thermodynamics study. Similar studies carried out with the control molecules showed no selectivity for CN. The mechanistic aspects of the reactivity of CN toward 5FLOH were supported by DFT computational study.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:112030
Deposited On:27 Nov 2017 12:13
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