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Fluorescent probe based on fluorescence quenching effect of coumarin on NO2, preparation method and application thereof

A fluorescent probe, fluorescence quenching technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc.

Active Publication Date: 2017-03-29
INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Coumarin molecules have the advantages of simple preparation, large Stokes shift, and high fluorescence brightness. They have good application prospects in the fields of dyes, sensing, and analysis and detection. Fluorescent probes based on coumarin are used for the labeling and detection of metal ions, free radicals, and small inorganic molecules. However, no coumarin-based fluorescent probes have been used for NO 2 Fluorescence Quenching Detection Applications

Method used

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  • Fluorescent probe based on fluorescence quenching effect of coumarin on NO2, preparation method and application thereof
  • Fluorescent probe based on fluorescence quenching effect of coumarin on NO2, preparation method and application thereof
  • Fluorescent probe based on fluorescence quenching effect of coumarin on NO2, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Example 1 Preparation of 4-N,N-dimethylamino-2-hydroxyl-benzaldehyde

[0027] 3-N,N-Dimethylaminophenol (10.5 g, 0.075 mol) was dissolved in 20 mL of dry DMF, and was added dropwise at room temperature to a mixture of phosphorus oxychloride (8.2 mL, 0.09 mol) and anhydrous DMF (17 mL, 0.22 mol) was added to freshly prepared Vilsmeier Haack reagent, then stirred at room temperature for 20 min, heated to 40° C. for 20 min, and then heated to 80° C. for 30 min. After cooling to room temperature, the reaction mixture was quickly poured into a large amount of ice water, and the above solution was washed with NaHCO 3 After neutralization, the precipitate was collected and filtered, washed with water and dried to obtain 8.8 g of the target product with a yield of 65%.

Embodiment 2

[0028] Example 2 Preparation of 7-N, N-dimethylamino-coumarin

[0029] 4-N,N-Dimethylamino-2-hydroxy-benzaldehyde (5g, 30mmol) and ethyl triphenylphosphinyl acetate (12g, 35mmol) were heated to 180°C for 1h under the protection of argon, then cooled After reaching room temperature, the crude product was separated and purified by silica gel column chromatography to obtain 5.5 g of the target product with a yield of 62%.

Embodiment 3

[0030] Example 3 Preparation of 7-N, N-dimethylamino-3-formyl coumarin

[0031] 7-N,N-Dimethylamino-coumarin (0.75g, 4.0mmol) was dissolved in dry 30mL of DMF, and added dropwise to phosphorus oxychloride (1.8mL, 20mmol) at room temperature and anhydrous DMF (4.0mL, 50mmol) in the newly prepared VilsmeierHaack reagent, then heated to 55°C for 4h, cooled to room temperature and stirred for 12h, then poured the reaction mixture into a large amount of ice water, filtered after standing, and collected the precipitate After drying, 0.30 g of the target product was obtained with a yield of 30%.

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Abstract

The invention discloses a fluorescent probe based on fluorescence quenching effect of coumarin on NO2, a preparation method and application thereof. The preparation method includes: utilizing 3-N, N-dimethylamino phenol, phosphorous oxychloride and anhydrous DMF to prepare 4-N, N-dimethylamino-2-hydroxy-benzaldehyde, then utilizing 4-N, N-dimethylamino-2-hydroxy-benzaldehyde and ethyl(triphenylphosphoranylidene)acetate to prepare 7-N, N-dimethylamino-coumarin, then reacting the 7-N, N-dimethylamino-coumarin with anhydrous DMF to obtain 7-N, N-dimethylamino-3-aldehyde coumarin, and finally utilizing 7-N, N-dimethylamino-3-aldehyde coumarin to react with hydroxylamine hydrochloride and triethylamine to obtain the probe 7-N, N-dimethylamino-3-oximino coumarin. The probe can be used for detecting NO2, when detection action occurs between the probe and NO2, the fluorescence intensity quenches by 98%.

Description

technical field [0001] The invention relates to the technical field of nitrogen dioxide detection, more specifically, the invention relates to a method based on coumarin for NO 2 Fluorescent probes for fluorescence quenching effects, preparation methods and applications thereof. Background technique [0002] NO 2 As a degradation product of nitroaliphatic explosives, which are atmospheric pollutants in the environment, the development of NO 2 The new detection method is of great significance for maintaining public safety and preventing environmental pollution. The fluorescence quenching method is to construct a macromolecular or copolymer sensing material with a fluorescent quenching small molecule as the sensing unit, which can realize super quenching of the detection object based on "one-point contact, multi-point response", and has a very high Sensitivity is one of the development trends in the field of analysis and detection, among which fluorescent small molecules ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1088G01N21/643G01N2021/6432
Inventor 陈建波赵川德于谦熊鹰睢贺良陈捷
Owner INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS