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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

Abstract

A new efficient pyrdine-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 Br group to the fluorophore skeleton at the ortho-position of hydrazone, generates reference compounds (4b-E, 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. High emission of the four fluorophores in the solid-state is also investigated. Moreover, probe 4a-E preloaded on test papers, upon cynaide treatment shows obvious changes in color and demonstrates 4a-E as a writable platform. More importantly, it exhibits great potential application for cyanides detection of cyanide-containing food materials and excellent performance in real-word water samples.

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Publication details

The article was accepted on 03 Nov 2019 and first published on 04 Nov 2019


Article type: Paper
DOI: 10.1039/C9AN01762C
Analyst, 2019, Accepted Manuscript

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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, Accepted Manuscript , DOI: 10.1039/C9AN01762C

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