Issue 4, 2015

A pyrenesulfonyl-imidazolium derivative as a selective cyanide ion sensor in aqueous media

Abstract

In this work, N-imidazolylpropyl pyrenesulfonamide 1 and its diimidazolium salt 2 were synthesized to be tested as cyanide (CN) sensors. The probes were found to be selective and sensitive toward CN in a PBS–EtOH solution. The sensing ability of the probes was examined by UV-Vis, fluorescence, and NMR spectroscopy. CN sensing was characterized by the quenching of both the monomer and excimer emissions of probe 2, owing to the unlocking of the π–π interaction; in the case of probe 1, a small degree of quenching of the monomer emission intensity was observed. The selective sensing of CN was associated with a color change and complete quenching of green fluorescence emission under 365 nm illumination. The degree of quenching of the emission intensity was driven by the presence of a positive charge, the number of positive charges (which lead to ionic interactions with anions), and hydrogen bonding. Probe 2 exhibited a large association constant with CN (Ka = 2.32 × 105 M−1), with a 1 : 2 stoichiometry in a PBS–EtOH solution. The lowest detection limit for the estimation of CN was determined to be 0.5 μM (13 ppb), which is lower than the permissible limit for drinking water established by the WHO.

Graphical abstract: A pyrenesulfonyl-imidazolium derivative as a selective cyanide ion sensor in aqueous media

Supplementary files

Article information

Article type
Paper
Submitted
18 Sep 2014
Accepted
02 Feb 2015
First published
02 Feb 2015

New J. Chem., 2015,39, 2935-2942

Author version available

A pyrenesulfonyl-imidazolium derivative as a selective cyanide ion sensor in aqueous media

A. Kumar and H. Kim, New J. Chem., 2015, 39, 2935 DOI: 10.1039/C4NJ01603C

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