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A new disulfide Schiff base as a versatile “OFF–ON–OFF” fluorescent–colorimetric chemosensor for sequential detection of CN and Fe3+ ions: combined experimental and theoretical studies

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Abstract

A new naphthaldehyde based disulfide fluorogenic and colorimetric chemosensor, N,N′-disulfandiylbis((2,1-phenylene))bis(1-(naphthalene-1-yl)methaneimine) (L), has been synthesized, and characterized by CHN analyses, X-ray crystallography and different spectroscopic methods. The detection of cyanide is accompanied by the cleavage of the S–S bond and nucleophilic attack of the cyanide ion on the imine group of the disulfide chemosensor with a 1 : 2 binding stoichiometry, as confirmed by 1H NMR studies. The specific reaction results in a significant fluorescence enhancement and a color change from pale yellow to orange. The LOD for cyanide detection is 2.5 × 10−7 M. The L chemosensor is used successfully for the detection of cyanide in electroplating wastewater and the fabrication of colorimetric test strips. The colorimetric and fluorogenic sensing mechanism of L toward CN is also investigated by DFT calculations and ESI-MS experiments. The emission of the [L-CN] system is quenched by Fe3+ ions and can be used as a sensitive and selective “ON–OFF” fluorescent sensor for the detection of Fe3+. The fluorogenic sensing can be applied for the fabrication of an INHIBIT type molecular logic gate.

Graphical abstract: A new disulfide Schiff base as a versatile “OFF–ON–OFF” fluorescent–colorimetric chemosensor for sequential detection of CN− and Fe3+ ions: combined experimental and theoretical studies

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Publication details

The article was received on 12 Jun 2019, accepted on 31 Jul 2019 and first published on 03 Aug 2019


Article type: Paper
DOI: 10.1039/C9NJ03049B
New J. Chem., 2019, Advance Article

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    A new disulfide Schiff base as a versatile “OFF–ON–OFF” fluorescent–colorimetric chemosensor for sequential detection of CN and Fe3+ ions: combined experimental and theoretical studies

    F. Nouri Moghadam, M. Amirnasr, K. Eskandari and S. Meghdadi, New J. Chem., 2019, Advance Article , DOI: 10.1039/C9NJ03049B

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