A kind of reactive hydrazine fluorescent probe and its preparation method and application

A fluorescent probe and reactive technology, which is applied in the detection trap fluorescent probe and its preparation field, can solve the problems of complex probe synthesis process, weak anti-interference, narrow linear range, etc., and achieve high yield and post-processing Convenience, compositing simple effects

Active Publication Date: 2022-03-08
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the currently reported probes for the detection of hydrazine are easily limited by various factors in the detection process, such as detection in a low pH environment, complex probe synthesis process, weak anti-interference, narrow linear range, long reaction time, High detection limit, etc.

Method used

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  • A kind of reactive hydrazine fluorescent probe and its preparation method and application
  • A kind of reactive hydrazine fluorescent probe and its preparation method and application
  • A kind of reactive hydrazine fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Preparation of 2-(2-chloro-7-diethylaminoquinolin-3-yl)methylenemalononitrile (QAM)

[0048] Add 0.23g (0.88mmol) 2-chloro-7-diethylaminoquinoline-3-carboxaldehyde, 0.10g (1.51mmol) propanedinitrile, add 4.00mL absolute ethanol, 0.2mL pyridine, 0.1 mL of glacial acetic acid was stirred under reflux until the reaction of 2-chloro-7-diethylaminoquinoline-3-carbaldehyde was complete (TLC tracking), cooled to room temperature, filtered with suction, washed with a small amount of ethanol, and dried to obtain 0.23 g of a red solid. Namely 2-(2-chloro-7-diethylaminoquinolin-3-yl)methylene malononitrile (QAM), yield 82.50%, 1 H NMR (400MHz, CDCl 3)δ8.90(s, 1H), 8.26(s, 1H), 7.71(d, J=9.3Hz, 1H), 7.12(dd, J=9.3, 2.6Hz, 1H), 6.98(d, J=2.4 Hz, 1H), 3.55 (q, J=7.1Hz, 4H), 1.29 (t, J=7.1Hz, 6H). IR(KBr), ν / cm-1:2226,1623. ESI-Ms: 311.23 (M+1).

Embodiment 2

[0050] Preparation of 2-(2-chloro-7-diethylaminoquinolin-3-yl)methylenemalononitrile (QAM)

[0051] Add 0.18g (0.69mmol) 2-chloro-7-diethylaminoquinoline-3-carbaldehyde, 0.06g (0.91mmol) acetonitrile, 3.50mL absolute ethanol, 0.2mL glacial acetic acid into a 50mL two-necked bottle, Reflux and stir for 14 hours, cool to room temperature, filter with suction, wash with a small amount of ethanol, and dry to obtain 0.19 g of a red solid. That is, 2-(2-chloro-7-diethylaminoquinolin-3-yl)methylenemalononitrile (QAM), with a yield of 88.83%. 1 H-NMR and ESI-MS characterization data are the same as in Example 1.

Embodiment 3

[0053] Preparation of 2-(2-chloro-7-diethylaminoquinolin-3-yl)methylenemalononitrile (QAM)

[0054] Add 0.18g (0.69mmol) 2-chloro-7-diethylaminoquinoline-3-carbaldehyde, 0.06g (0.91mmol) propanedinitrile, 3.50mL absolute ethanol, 0.1mL pyridine, and reflux in a 50mL two-necked bottle. Stir for 14 h, cool to room temperature, filter with suction, wash with a small amount of ethanol, and dry to obtain 0.18 g of a red solid. That is, 2-(2-chloro-7-diethylaminoquinolin-3-yl)methylenemalononitrile (QAM), with a yield of 84.15%. 1 H-NMR and ESI-MS characterization data are the same as in Example 1.

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Abstract

The invention provides a reactive fluorescent probe, its preparation method and its application in detecting hydrazine. The probe specifically involved is 2-(2-chloro-7-diethylaminoquinolin-3-yl)methylenemalononitrile (QAM). It is prepared by condensation reaction using 2-chloro-7-diethylaminoquinoline-3-formaldehyde and malononitrile as raw materials. After different concentrations of hydrazine interacted with QAM, under 365nm ultraviolet light, the solution containing QAM could be seen with the naked eye, and the filter paper sheet and thin-layer silica gel plate changed from orange-yellow fluorescence to blue-green fluorescence. The minimum detection limit of hydrazine by fluorescence spectrophotometry is 3.9849×10 ‑9 mol / L. The invention can qualitatively and quantitatively detect hydrazine in samples from different sources by fluorescence spectrophotometry, does not need complicated devices and professional technicians during the detection, is convenient to operate, low in cost, fast in response speed and high in sensitivity.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis and analysis and detection, and in particular relates to a fluorescent probe of a detection trap, a preparation method thereof and an application in the detection trap. Background technique [0002] Hydrazine, also known as "hydrazine", is widely used in agriculture, chemistry and pharmaceutical fields as a highly reactive base, nucleophile and reducing agent, and is also used in aviation, aerospace and fuel for its high heat energy battery field. However, as a neurotoxin, hydrazine is easily absorbed through the skin, oral or inhalation routes, causing irreversible damage to the liver, lungs, kidneys, blood and central nervous system. According to data, hydrazine is a known genotoxic compound with potential carcinogenic, teratogenic and mutagenic effects. Hydrazine is classified as an extremely toxic substance as an environmental pollutant because of its wide application, easy absorp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/38C09K11/06G01N21/64
CPCC09K11/06C07D215/38G01N21/643G01N21/6447C09K2211/1029
Inventor 但飞君潘彤李玉杰唐倩兰海闯
Owner CHINA THREE GORGES UNIV
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