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A kind of preparation method and application of bifluoroboron fluorescent dye responsive to triethylamine

A fluorescent dye and triethylamine technology, which is applied in the direction of luminescent materials, organic dyes, azo dyes, etc., can solve the problems of long reaction time, complicated operation method of triethylamine, low sensitivity, etc., and achieve fast detection and stable peak value change , the effect of low fluorescence intensity

Active Publication Date: 2022-08-09
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Most of the existing domestic and foreign methods of using different fluorescent probes to detect triethylamine have defects such as complicated operation methods, long reaction time, and low sensitivity.

Method used

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  • A kind of preparation method and application of bifluoroboron fluorescent dye responsive to triethylamine
  • A kind of preparation method and application of bifluoroboron fluorescent dye responsive to triethylamine
  • A kind of preparation method and application of bifluoroboron fluorescent dye responsive to triethylamine

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Experimental program
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Effect test

Embodiment 1 Embodiment 1

[0023] Example 1 Example 1 Synthesis of Probe Molecules

Embodiment 1-1

[0025] Take compound 1 (598 mg, 2 mmol); salicylaldehyde (1.96 ml, 2 mmol), TsOH (34.2, mg, 0.2 mmol) were dissolved in DCM (60 ml), stirred at 35 ° C for 12 h, and the reaction was monitored by spot plate until the raw materials were completely reacted, After neutralization with alkali, the product was washed with water, extracted, dried, rotary evaporated, and purified by filtration to obtain compound 3 (216 mg, yield 26.7%). Take the above compound 3 (202mg, 0.5mmol), add 20ml dichloromethane solution, 1.00ml triethylamine, under electromagnetic stirring, slowly add boron trifluoride ether solution (1.00ml) dropwise, raise the temperature to 35 ℃ , refluxed for 30 min, TLC spot plate detection, the product was washed with water, extracted, dried, rotary evaporated, filtered and purified to obtain compound I as a golden yellow solid (194 mg, yield 86%).

[0026]

Embodiment 1-2

[0028] Take compound 1 (598 mg, 2 mmol); salicylaldehyde (1.96 ml, 2 mmol), TsOH (17.1, mg, 0.1 mmol), dissolve in DCM (60 ml), stir at 35 ° C for 12 h, and monitor the reaction by spotting until the raw materials are completely reacted, After neutralization with alkali, the product was washed with water, extracted, dried, rotary evaporated, and purified by filtration to obtain compound 3 (299 mg, yield 37%). Take the above compound 3 (202mg, 0.5mmol), add 20ml dichloromethane solution, 1.00ml triethylamine, under electromagnetic stirring, slowly add boron trifluoride ether solution (1.00ml) dropwise, raise the temperature to 35 ℃ , refluxed for 30 min, TLC spot plate detection, the product was washed with water, extracted, dried, rotary evaporated, filtered and purified to obtain compound I as a golden yellow solid (198.4 mg, yield 88%). Compared with Example 1-1, the amount of p-toluenesulfonic acid was reduced by half, and the yield of compound 3 was increased by 10.3%.

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Abstract

The invention discloses a preparation method and application of a fluorescent dye with a bifluoroboron structure responsive to alkalis. Heptafluoroboron compound 1 and dichloromethane are added to a reaction flask at room temperature, stirred and dissolved, and then saliculus is added. Aldehyde and p-toluenesulfonic acid are heated and refluxed to react to obtain reaction solution 1, the temperature of heating and refluxing reaction is 35-40 ° C, and refluxing for 2-18 h; then add dichloromethane, triethylamine, and slowly add boron trifluoride ether complex dropwise compound, heating and refluxing reaction to obtain reaction solution 2, heating and refluxing reaction temperature is 35-40 DEG C, refluxing for 2-18h to obtain a double fluoroboron structure fluorescent dye compound. The molar amount of triethylamine can be distinguished by different fluorescence intensities, and the change of the molar amount of triethylamine in the DCM liquid environment can be detected. Ethylamine has a large molar range, and is not color-producing in acidic and neutral solutions, that is, stable in the fluorescence spectrum.

Description

technical field [0001] The invention discloses a preparation method and application of a fluorescent dye with a bifluoroboron structure responsive to triethylamine, in particular to a fluorescent dye that can distinguish the molar amount of triethylamine by different fluorescence intensities, and can detect DCM Changes in the molar amount of triethylamine in a liquid environment. Background technique [0002] Triethylamine is a volatile organic amine, which is a moderately toxic compound. If inhaled, it may cause abnormal symptoms in the respiratory organs and blood circulatory system, including the central system and the body's liver. It can cause oral corrosion and even pulmonary edema and cause chemical burns. For female patients, if the components of triethylamine are inhaled, infertility will also occur. [0003] Triethylamine is often used as an acid binding agent in production, and is finally discharged as wastewater. The concentration of triethylamine in wastewater...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09B57/00C09K11/06G01N21/64
CPCC07F5/022C09B57/00C09K11/06G01N21/643C09K2211/1055C09K2211/104Y02B20/00
Inventor 张诺诺袁晓慧晏佳莹胡聪刘德保郑开波
Owner CHINA THREE GORGES UNIV