Issue 12, 2017

A smart ratiometric red fluorescent chemodosimeter for fluoride based on anthraquinone nosylate

Abstract

The present work reports a smart design of a chemodosimeter, namely 4-(6,11-dihydro-6,11-dioxo-1H-anthra[1,2-d]imidazol-2-yl)phenyl-4-nitrobenzenesulfonate (AH), which recognises F specifically through a naked eye colour change from light yellow to light orange and remarkable ratiometric fluorescence from green to red from the matrix of a large number of similar anions in acetonitrile solution. The sensing mechanism was worked out as fluoride-triggered deprotonation of imidazole accompanied by deprotection of nosylate group (p-nitrobenzenesulfonate group). AH was fully characterized through single crystal X-ray diffraction studies along with FT-IR, 1H and 13C NMR and ESI-MS. The detection limit calculated through fluorescent titration was found to be 3.45 × 10−10 M. Theoretical calculations at density functional level were in agreement with experimental observations. AH also showed its practical applicability in the form of test paper strips.

Graphical abstract: A smart ratiometric red fluorescent chemodosimeter for fluoride based on anthraquinone nosylate

Supplementary files

Article information

Article type
Paper
Submitted
09 May 2017
Accepted
15 May 2017
First published
16 May 2017

New J. Chem., 2017,41, 5098-5104

A smart ratiometric red fluorescent chemodosimeter for fluoride based on anthraquinone nosylate

Shweta, A. Kumar, Neeraj, S. K. Asthana and K. K. Upadhyay, New J. Chem., 2017, 41, 5098 DOI: 10.1039/C7NJ01575E

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