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Pyridine-hydrazone-controlled cyanide detection in aqueous media and solid-state: tuning the excited-state intramolecular proton transfer (ESIPT) fluorescence modulated by intramolecular NH⋯Br hydrogen bonding

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Abstract

A new efficient pyridine-hydrazone-substituted naphthalimide receptor 4a-E has been synthesized as a selective colorimetric and fluorescent chemosensor for cyanide sensing in aqueous environments through a unique excited-state intramolecular proton transfer (ESIPT) mechanism. The addition of a Br group to the fluorophore skeleton at the ortho-position of hydrazone generates reference compounds (4b-E and 4c-Z). Interestingly, the potential intramolecular NH⋯Br hydrogen bonding might compete with the anion-induced intermolecular NH⋯A hydrogen bonding, resulting in dramatic ESIPT suppression. The high emission of probe 4a-E and other control probes in solid-state is also investigated. Moreover, probe 4a-E preloaded on test papers, upon cyanide treatment, shows obvious changes in color which demonstrates that 4a-E is a writable platform. More importantly, it exhibits great potential application for the detection of cyanide in food materials and excellent performance in real-world water samples.

Graphical abstract: Pyridine-hydrazone-controlled cyanide detection in aqueous media and solid-state: tuning the excited-state intramolecular proton transfer (ESIPT) fluorescence modulated by intramolecular NH⋯Br hydrogen bonding

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Publication details

The article was received on 07 Sep 2019, accepted on 03 Nov 2019 and first published on 04 Nov 2019


Article type: Paper
DOI: 10.1039/C9AN01762C
Analyst, 2019, Advance Article

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    Pyridine-hydrazone-controlled cyanide detection in aqueous media and solid-state: tuning the excited-state intramolecular proton transfer (ESIPT) fluorescence modulated by intramolecular NH⋯Br hydrogen bonding

    C. Rao, Z. Wang, Z. Li, L. Chen, C. Fu, T. Zhu, X. Chen, Z. Wang and C. Liu, Analyst, 2019, Advance Article , DOI: 10.1039/C9AN01762C

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