Pyrene derivative fluorescent probe molecule for recognizing and detecting formaldehyde as well as preparation method and application of fluorescent probe molecule

A technology of pyrene derivatives and fluorescent probes is applied in the field of identifying and preparing pyrene derivatives fluorescent probe molecules for detecting formaldehyde, which can solve the problems of high cytotoxicity, complicated preparation methods, inability to use formaldehyde detection agents, etc. The effect of low toxicity, simple and easy-to-obtain raw materials, and high fluorescence quantum yield

Active Publication Date: 2018-05-18
河南省农业科学院农业质量标准与检测技术研究所
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0004] The present invention proposes a pyrene derivative fluorescent probe molecule for identifying and detecting formaldehyde and its preparation method and application, which solves th

Method used

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  • Pyrene derivative fluorescent probe molecule for recognizing and detecting formaldehyde as well as preparation method and application of fluorescent probe molecule
  • Pyrene derivative fluorescent probe molecule for recognizing and detecting formaldehyde as well as preparation method and application of fluorescent probe molecule
  • Pyrene derivative fluorescent probe molecule for recognizing and detecting formaldehyde as well as preparation method and application of fluorescent probe molecule

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Experimental program
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Embodiment 1

[0031] A preparation method for a pyrene derivative fluorescent probe molecule that recognizes and detects formaldehyde:

[0032] In a one-necked flask, potassium allyl trifluoroborate (148 mg, 1 mmol) was dissolved in 12.4 mL of ammonia-methanol solution (concentration: 7 mol / L), and stirred at room temperature for 15 min under nitrogen protection. Dissolve 1-pyrene formaldehyde (115 mg, 0.5 mmol) in 19.2 mL of ammonia-methanol solution (concentration: 7 mol / L), add 115 μL of water, and inject the reaction solution into the allyl potassium trifluoroborate Ammonia-methanol solution was reacted at room temperature for 10 h. After the reaction was completed, the solvent was removed under reduced pressure by a rotary evaporator to obtain a crude product. After separation by silica gel column chromatography (eluent: ethyl acetate:petroleum ether=1:3, volume ratio), 88 mg of yellow solid was obtained as product B1, and the yield was 65%.

[0033] NMR measurement: 1H NMR (CDCl3, 4...

Embodiment 2

[0035] A preparation method for a pyrene derivative fluorescent probe molecule that recognizes and detects formaldehyde:

[0036] In a one-necked flask, potassium allyl trifluoroborate (148 mg, 1 mmol) was dissolved in 43.4 mL of ammonia-methanol solution (concentration: 7 mol / L), and stirred at room temperature for 15 min under nitrogen protection. Dissolve 1-pyrenecarbaldehyde (57.5 mg, 0.25 mmol) in 19.2 mL of ammonia-methanol solution (concentration: 7 mol / L), add 12 μL of water, and inject the reaction solution into the allyl potassium trifluoroborate Ammonia-methanol solution was reacted at room temperature for 15 h. After the reaction was completed, the solvent was removed under reduced pressure by a rotary evaporator to obtain a crude product. After separation by silica gel column chromatography (eluent: ethyl acetate:petroleum ether=1:6, volume ratio), 50.8 mg of yellow solid was obtained as product B1, and the yield was 75%.

[0037]NMR measurement: 1H NMR (CDCl3, ...

Embodiment 3

[0039] A preparation method for a pyrene derivative fluorescent probe molecule that recognizes and detects formaldehyde:

[0040] In a one-necked flask, potassium allyl trifluoroborate (148 mg, 1 mmol) was dissolved in 74.4 mL of ammonia-methanol solution (concentration: 7 mol / L), and stirred at room temperature for 15 min under nitrogen protection. Dissolve 1-pyrene formaldehyde (28.8 mg, 0.13 mmol) in 19.2 mL of ammonia-methanol solution (concentration: 7 mol / L), add 12 μL of water, and inject the reaction solution into the allyl potassium trifluoroborate Ammonia-methanol solution was reacted at room temperature for 20 h. After the reaction was completed, the solvent was removed under reduced pressure by a rotary evaporator to obtain a crude product. After separation by silica gel column chromatography (eluent: ethyl acetate:petroleum ether=1:6, volume ratio), 30.5 mg of yellow solid was obtained as product B1, and the yield was 90%.

[0041] NMR measurement: 1H NMR (CDCl3...

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Abstract

The invention provides a pyrene derivative fluorescent probe molecule for recognizing and detecting formaldehyde as well as a preparation method and application of the fluorescent probe molecule. Thepreparation method provided by the invention has simple synthetic steps only needs one step reaction and has a higher yield. The fluorescent probe provided by the invention does not have fluorescencein an HEPES buffer system, but can react specifically with the formaldehyde to generate a product with strong fluorescence, so as to achieve specific selection and quantitative analysis for the formaldehyde. The recognition characteristics of the probe B1 with aldehydes and amino acids in the HEPES buffer system are studied by a fluorescence spectrometer, results show that the probe B1 has high-efficiency specific selectivity for the formaldehyde, the lowest detection limit of the probe for the formaldehyde is 0.107[mu]M, and the probe has broad application prospects in the field of biomolecule detection.

Description

technical field [0001] The invention relates to a formaldehyde detection agent, in particular to a pyrene derivative fluorescent probe molecule for recognizing and detecting formaldehyde and its preparation method and application. Background technique [0002] Formaldehyde is a recognized highly toxic substance, which has a great harmful effect on biological cells. Long-term intake of formaldehyde-contaminated food will cause paralysis of the central nervous system, further causing a series of hazards such as pulmonary edema, hepatic coma, and renal failure. The World Health Organization has confirmed that formaldehyde is a teratogenic and carcinogenic substance, and long-term exposure and intake can lead to gene mutations. There are many detection methods for formaldehyde. At present, the common laboratory detection methods include spectrophotometry and chromatography. The spectrophotometric method refers to NY / T1283-2007, SC / T3025-2006, GB / T 5009.49-2008 and SN / T2183-2008...

Claims

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Application Information

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IPC IPC(8): C07C211/57C07C209/68C09K11/06G01N21/64
CPCC07C211/57C09K11/06C09K2211/1011G01N21/6428
Inventor 张迪贾斌尹海燕刘继红李漫王允王铁良刘冬梅曹成李淑芳周玲张军锋孙江南俎建英
Owner 河南省农业科学院农业质量标准与检测技术研究所
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