A highly selective and sensitive dual-channel chemosensor for cyanide based on sulfahydrazone derivative

GRAPHICAL ABSTRACT

ABSTRACT

A colorimetric and fluorescent cyanide probe bearing naphthol and sulfahydrazone groups has been designed and synthesized. This structurally simple probe displays a rapid response and high selectivity for cyanide in DMSO/EtOH (v/v = 2:8) solution. The addition of CN⁻ to the sensor p-toluenesulfonyl-2-hydroxy-1-naphthylhydrazone (L3) induced a remarkable color change from pale-yellow to yellow, and green fluorescence changed to yellow. The ¹H NMR titration and DFT calculations suggested that the selective sensing process is based on a nucleophilic addition reaction of cyanide to imine. Test strips based on sensor L3 were fabricated, which could act as a convenient and efficient test kit to detect CN⁻ for “in-the-field” measurements.

KEYWORDS:

• Cyanide(CN⁻)
• chemosensor
• nucleophilic addition
• DFT

Funding

This work was supported by the National Natural Science Foundation of China (Nos. 21262032, 21161018, and 21574104), the Program for Changjiang Scholars and Innovative Research Team in University of Ministry of Education of China (No. IRT1177), the Natural Science Foundation of Gansu Province (No. 1010RJZA018), the Youth Foundation of Gansu Province (No. 2011GS04735) and NWNU-LKQN-11-32.