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Fluorescent probe with chalcone structure, preparation method of fluorescent probe and application of fluorescent probe in hydrazine detection

A fluorescent probe and chalcone technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of long synthesis route, unsatisfactory detection, low yield, etc., and achieve short synthesis route and high yield. High efficiency and easy post-processing

Active Publication Date: 2021-06-22
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the reported fluorescent probes for the detection of hydrazine show good sensitivity and selectivity for hydrazine, but these probes also have disadvantages such as long synthetic routes, low yields, and unsatisfactory detection.

Method used

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  • Fluorescent probe with chalcone structure, preparation method of fluorescent probe and application of fluorescent probe in hydrazine detection
  • Fluorescent probe with chalcone structure, preparation method of fluorescent probe and application of fluorescent probe in hydrazine detection
  • Fluorescent probe with chalcone structure, preparation method of fluorescent probe and application of fluorescent probe in hydrazine detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of 3-(3'-(2'-chloro-7'-diethylaminoquinoline propenone-7-diethylaminocoumarin (QCT-Cl) Weigh 2-chloro-7-diethylaminoquinone Add 7-diethylaminocoumarin-3-ethanone to a 100mL two-neck bottle, add solvent, stir to dissolve, then add catalyst, the solution is reddish brown, heat up to 75°C, and detect the reaction by TLC Process. After the completion of the reaction, cool to room temperature to precipitate an orange solid, pressurize suction filtration, and wash with ethanol to obtain an orange solid, which is 3-(3'-(2'-chloro-7'-diethylaminoquinoline propene Keto-7-diethylaminocoumarin.

[0029] In the above-mentioned preparation method, some conditions are changed, and the yield effect is as follows:

[0030]

[0031]

[0032] Example 1-1 obtained 4.12 g of orange solid with a yield of 82%. m.p.:212-213℃. 1 H NMR (400MHz, CDCl 3 )δ8.60(s,1H),8.42(s,1H),8.24(dd,J=39.2,15.6Hz,2H),7.69(d,J=9.2Hz,1H),7.45(d,J=4.4 Hz,1H),7.10(dd,J=9.2,2.8Hz,1H),6.99(d,J=...

Embodiment 2

[0033] The preparation of embodiment 2 test solutions

[0034] (1) Preparation procedure of stock solution:

[0035] In a 10 mL vial, make up 10 in DMSO -3 The mol / L QCT-Cl stock solution is ready for use. In a 2mL sample bottle, add 0.2mL double-distilled water, then add 1.8mL DMSO, and then add 0.01mol / L of the hydrazine standard solution (20μL, 10 -2 mol / L), mix well; finally add 20 μL of QCT-Cl in DMSO solution (10 -3 mol / L), and mix again. After standing for 0.5 hours, measure its fluorescence emission spectrum (380nm is the excitation wavelength). The above operation, without adding the sample solution to be tested, is the preparation of the blank test solution.

[0036] (2) Fluorescence spectrum test:

[0037] The blank test solution of QCT-Cl has a weak fluorescence emission peak at 460nm; when hydrazine exists, the fluorescence at 460nm increases; and with the increase of hydrazine concentration, the intensity increases significantly, see image 3 .

[0038] (...

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Abstract

The invention provides a fluorescent probe based on a chalcone structure, a preparation method and application of the fluorescent probe in hydrazine detection. In particular, the related probe is 3-(3 '-(2'-chloro-7 '-(diethylamino) quinolyl) allyl acetone)-7-diethylamino coumarin (QCT-Cl). The probe QCT-Cl is prepared by taking 2-chloro-7-diethylaminoquinoline formaldehyde and 7-diethylaminocoumarin-3-ethanone as raw materials through condensation reaction, the synthesis condition is mild, and the purification is simple. The QCT-Cl is a fluorescence enhanced fluorescent probe, after hydrazine acts on the QCT-Cl, it can be seen that a solution of the QCT-Cl changes into brilliant blue from weak red under an ultraviolet lamp through naked eyes, the QCT-Cl has high selectivity, high anti-interference performance and high sensitivity, the lowest detection limit of hydrazine detection is 9.46 * 10 <-8 > mol / L, and the QCT-Cl can be used as a fluorescent probe for qualitative and quantitative hydrazine detection. The probe is widely applied to hydrazine detection in environmental and biological fields.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, analysis and detection, and in particular relates to a fluorescent probe for detecting hydrazine, a preparation method thereof and an application in detecting hydrazine. Background technique [0002] Hydrazine (Hydrazine, NH 2 NH 2 ), also known as "hydrazine", as a strong reducing agent, highly active base and nucleophile, is widely used in fields such as metal anticorrosion, textile dyes, medicine, chemical industry, etc. Aviation, aerospace and fuel cell fields. However, as a neurotoxin, hydrazine can easily cause irreversible damage to human liver, lung, kidney, blood and central nervous system through oral cavity, skin penetration or inhalation. In addition, hydrazine, as a genotoxic compound, has potential carcinogenic, teratogenic, and mutagenic effects. According to the national occupational health standard GBZ2.1-2007 of the People's Republic of China, the time-weighted ave...

Claims

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Application Information

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IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC07D405/06C09K11/06G01N21/6428G01N2021/6439C09K2211/1029C09K2211/1088
Inventor 但飞君唐倩陈鸿卫巧郭涛
Owner CHINA THREE GORGES UNIV
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