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Rational design of a novel turn-on fluorescent probe for the detection and bioimaging of hydrazine with barbituric acid as a recognition group

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Abstract

A novel turn-on fluorescent probe with barbituric acid as a unique recognition group has been rationally designed and synthesized using a facile method for detecting hydrazine. The 5-((7-(dimethylamino)-4,5-dihydronaphtho [1,2-b] thiophen-2-yl)methylene)pyrimidine-2,4,6 (1H,3H,5H)-trione (DPT) probe displays a large emission signal ratio variation (more than a 40-fold enhancement) in the presence of hydrazine under neutral conditions. Interestingly, a novel recognition mechanism based on a hydrazine-triggered addition–cyclisation-retro aldol was proposed and confirmed. Additionally, the DPT probe exhibits a low detection limit (5 × 10−8 M), applicable to the physiological pH range (3–12), a broad linear response range for hydrazine concentrations between 0 and 34 μM and a large Stokes shift (147 nm) for hydrazine detection in aqueous solution. Moreover, the DPT probe was successfully implemented for hydrazine imaging in vivo.

Graphical abstract: Rational design of a novel turn-on fluorescent probe for the detection and bioimaging of hydrazine with barbituric acid as a recognition group

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Publication details

The article was received on 15 Oct 2019, accepted on 14 Nov 2019 and first published on 18 Nov 2019


Article type: Paper
DOI: 10.1039/C9AN02058F
Analyst, 2020, Advance Article

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    Rational design of a novel turn-on fluorescent probe for the detection and bioimaging of hydrazine with barbituric acid as a recognition group

    J. Du, X. Li, S. Ruan, Y. Li, F. Ren, Y. Cao, X. Wang, Y. Zhang, S. Wu and J. Li, Analyst, 2020, Advance Article , DOI: 10.1039/C9AN02058F

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