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Fluorescent probe based on aggregation-induced emission mechanism, preparation method of fluorescent probe and application of fluorescent probe in detection of methylamphetamine in sewage

A technology of aggregation-induced luminescence and fluorescent probes, applied in the application of methamphetamine, fluorescent probes and its preparation field, can solve the problems of slow detection speed, detection lag, and inability to carry large instruments, so as to reduce the concentration of high concentrations Influence, good sensitivity, effect of improving detection precision and accuracy

Active Publication Date: 2022-03-01
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in a real crime scene, it is impossible to carry large-scale instruments for on-site detection, which exposes many shortcomings of instrument analysis and detection, such as complex operation, which requires long-term training by professionals; slow detection speed, unable to adapt to a large number of on-site inspections; The detection is lagging behind, and the samples seized at the scene cannot be quickly tested in time, etc.
With the diversification of drug flooding methods, the previous detection methods can no longer quickly combat drug crimes, so it is urgent to develop a material to quickly and accurately detect drugs

Method used

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  • Fluorescent probe based on aggregation-induced emission mechanism, preparation method of fluorescent probe and application of fluorescent probe in detection of methylamphetamine in sewage
  • Fluorescent probe based on aggregation-induced emission mechanism, preparation method of fluorescent probe and application of fluorescent probe in detection of methylamphetamine in sewage
  • Fluorescent probe based on aggregation-induced emission mechanism, preparation method of fluorescent probe and application of fluorescent probe in detection of methylamphetamine in sewage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 Fluorescent probe TPE-2COOH@γ-CD

[0034] The synthetic route of fluorescent probe TPE-2COOH@γ-CD is as follows figure 1 shown.

[0035] The preparation process of the fluorescent probe TPE-2COOH@γ-CD is as follows:

[0036] 1) Put 3,5-dicarboxyphenylboronic acid (0.50g), absolute ethanol (100mL), and 98% concentrated sulfuric acid (3mL) into a three-necked flask, and reflux at 80°C for 12 hours. The resulting solution was concentrated to 50 mL by evaporation, added water (100 mL) and filtered to give 1,3-diethylisophthalate-5-boronic acid as a white solid in 89.4% yield.

[0037] 2) Bromotriphenylethylene (1.34g, 4mmol), 1,3-diethylisophthalate-5-boronic acid (1.06g, 4mmol), anhydrous potassium carbonate (1.38g, 10.0mmol) , tetramethylammonium bromide (TBAB) (0.01g, 0.03mmol) and tetrakis(triphenylphosphine)palladium (115.6mg, 0.1mmol) were put into a 150mL round bottom flask, tetrahydrofuran (40mL) and water (5 mL), the resulting mixture was stirred at 80 ...

Embodiment 2

[0040] Example 2 Aggregation-induced Luminescent Properties of Fluorescent Probe TPE-2COOH@γ-CD

[0041] Such as figure 2 As shown, the absorption spectrum of the fluorescent probe does not overlap with the fluorescence emission spectrum, and has a large Stokes shift (158nm), which can avoid background fluorescence signal interference due to the overlapping of the excitation spectrum and the emission spectrum, and improve the accuracy of detection. sex. Such as image 3 As shown, the aggregation-induced luminescence properties of the fluorescent probe TPE-2COOH@γ-CD were first tested by fluorescence spectroscopy. In pure THF solvent, the fluorescence intensity of the fluorescent probe TPE-2COOH@γ-CD was almost 0, which is Because TPE-2COOH@γ-CD is in a dispersed state, the benzene ring on tetraphenylethylene rotates around the carbon-carbon double bond, so that the excited state energy decays in a non-radiative form; and when the water content in the mixed system reaches 90...

Embodiment 3

[0042] Example 3 Determination of critical aggregation concentration of fluorescent probe TPE-2COOH@γ-CD

[0043] Such as Figure 4 As shown, when the concentration is small, TPE-2COOH@γ-CD can rotate freely in the solution, and with the increase of its solution concentration, TPE-2COOH@γ-CD will aggregate. Therefore, in this experiment, the critical aggregation concentration (CAC) of TPE-2COOH@γ-CD was determined by fluorescence spectroscopy. Fluorescent probes of different masses were added into distilled water, ultrasonically dispersed, and prepared into a dispersion of 0.001 mg / mL to 1 mg / mL, and the critical aggregation concentration (CAC) of the fluorescent probe in the aqueous solution was determined by fluorescence spectroscopy. Such as Figure 2-Figure 8 As shown, the aqueous solution of TPE-2COOH@γ-CD emits weakly at low concentration, and when the concentration exceeds 0.25 mg / mL, the fluorescence intensity increases rapidly, so the critical aggregation concentrat...

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Abstract

The invention relates to the technical field of fluorescent probe compounds, in particular to a fluorescent probe based on an aggregation-induced emission mechanism, a preparation method of the fluorescent probe and application of the fluorescent probe to detection of methylamphetamine in sewage. The fluorescent probe TPE-2COOH (at) gamma-CD is obtained by compounding an AIE molecule TPE-2COOH with gamma-CD through an esterification reaction. The gamma-CD captures methylamphetamine in a solution through a size matching effect, and due to the fact that the subject-object interaction capacity of methylamphetamine and cyclodextrin is superior to the acting force between cyclodextrin and TPE-2COOH, when methylamphetamine enters a cavity of the gamma-CD, TPE-2COOH is replaced, fluorescence quenching is caused, and detection of methylamphetamine is achieved. The blue fluorescent probe disclosed by the invention can be used for rapidly detecting p-methylamphetamine in urban sewage.

Description

technical field [0001] The invention relates to the technical field of fluorescent probe compounds, in particular to a fluorescent probe based on an aggregation-induced luminescence mechanism, a preparation method thereof, and an application in detecting methamphetamine in sewage. Background technique [0002] Drugs are a major public hazard to society, seriously endangering human health and social peace. Methamphetamine is a new type of drug, a central nervous system stimulant with sympathomimetic effects, it can be used as a central nervous system stimulant for the treatment of narcolepsy and depression and other diseases. In recent years, the frequent occurrence of drug crimes has gradually become a severe test for countries around the world. In the process of drug control, there has always been a problem that has plagued the drug control department, and that is how to quickly detect drugs. Compared with other detection methods, fluorescent chemical sensors have the adv...

Claims

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Application Information

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IPC IPC(8): C08B37/16C07C67/343C07C69/80C07C51/09C07C63/66C09K11/06G01N21/64
CPCC08B37/0015C07C67/343C07C51/09C09K11/06G01N21/6428C09K2211/145C09K2211/1425G01N2021/6432C07C69/80C07C63/66
Inventor 娄振宁郝晓迈阚丽欣冯小庚熊英
Owner LIAONING UNIVERSITY
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