A coumarin chalcone ratiometric fluorescent probe for hydrazine based on deprotection, addition and subsequent cyclization mechanism

Miaomiao Xing; Kangnan Wang; Xiangwen Wu; Shuyue Ma; Duxia Cao; Ruifang Guan; Zhiqiang Liu

doi:10.1039/C9CC08174G

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A coumarin chalcone ratiometric fluorescent probe for hydrazine based on deprotection, addition and subsequent cyclization mechanism†

Miaomiao Xing,^a Kangnan Wang,^a Xiangwen Wu,^b Shuyue Ma,^a Duxia Cao,

*^a Ruifang Guan

*^a and Zhiqiang Liu

*^c

Author affiliations

* Corresponding authors

^a School of Materials Science and Engineering, University of Jinan, Jinan 250022, Shandong, China
E-mail: duxiacao@ujn.edu.cn, mse_guanrf@ujn.edu.cn

^b College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan 250014, Shandong, China

^c State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, Shandong, China
E-mail: zqliu@sdu.edu.cn

Abstract

A ratiometric fluorescent probe for hydrazine based on a coumarin chalcone framework and a levulinic acid terminal group with a low detection limit (0.1 ppb, 0.003 μM), a large ratiometric fluorescence change (I₄₆₅/I₅₇₅, 1265-fold enhancement) and a wide pH work range (3.0–12.0) was developed. The mechanism analysis of the isolated hydrazine product characterized by NMR, HRMS and the crystal structure indicates that the levulinic acid group is firstly removed by deprotection and then the dihydropyrazole ring is formed due to the addition and subsequent cyclization reaction in the presence of hydrazine.

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DOI: https://doi.org/10.1039/C9CC08174G
Article type: Communication
Submitted: 18 Oct 2019
Accepted: 19 Nov 2019
First published: 20 Nov 2019

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Chem. Commun., 2019,55, 14980-14983

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A coumarin chalcone ratiometric fluorescent probe for hydrazine based on deprotection, addition and subsequent cyclization mechanism

M. Xing, K. Wang, X. Wu, S. Ma, D. Cao, R. Guan and Z. Liu, Chem. Commun., 2019, 55, 14980 DOI: 10.1039/C9CC08174G

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Chemical Communications

A coumarin chalcone ratiometric fluorescent probe for hydrazine based on deprotection, addition and subsequent cyclization mechanism†

Abstract

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A coumarin chalcone ratiometric fluorescent probe for hydrazine based on deprotection, addition and subsequent cyclization mechanism

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