Fluorescent sensing material with sensing function to phenyl amine compounds, method and application thereof

A fluorescence sensing and compound technology, applied in the field of fluorescence sensing materials, can solve the problems of slow detection, low sensitivity, and complicated pretreatment of detection methods, and achieve the effects of easy film formation, good selectivity, and easy mass synthesis.

Inactive Publication Date: 2009-10-07
上海新微科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In summary, in view of the shortcomings of the existing detection methods such as slow detection, complicated pretreatment, expensive instruments, poor selectivity and low sensitivity, etc.

Method used

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  • Fluorescent sensing material with sensing function to phenyl amine compounds, method and application thereof
  • Fluorescent sensing material with sensing function to phenyl amine compounds, method and application thereof
  • Fluorescent sensing material with sensing function to phenyl amine compounds, method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1 (synthesis of TPA-Py)

[0046]

[0047] Under argon protection, 1.66g (4.47mmol) triphenylamine boric acid, 0.26g Pd(PPh 3 ) 4 (0.22mmol), 2.05g (14.86mmol) K 2 CO 3 , 7.44 ml H 2 O, 0.354 ml (3.71 mmol) of 2-bromopyridine and 30 ml of tetrahydrofuran were heated to 85° C. to react overnight. Extract with dichloromethane, and combine the organic phases. Washed with water, washed with saturated brine, anhydrous MgSO 4 dry. The yellow powder separated by column chromatography was 1.23 g, and the yield was 90%. 1 H NMR (500MHz CDCl 3 ): δ8.66(d, 1H), 7.87(d, 2H), 7.72(t, 1H), 7.67(d, 1H), 7.26(t, 3H), 7.18(t, 1H), 7.14(6H) , 7.04(t,2H), .MALDI-TOF MS m / z: 322

Embodiment 2

[0048] Embodiment 2 (synthesis of Br-BTD-Py)

[0049]

[0050] Under argon protection, 5.48g (18.64mmol) of 4,7-dibromo-2,1,3-benzothiadiazole, 1.07g Pd(PPh 3 ) 4 (0.93mmol), 6.86g 2-tributyltinylpyridine (18.64mmol), dissolved in 100ml of toluene. Heated to 125°C for 3 days. Extract with dichloromethane, and combine the organic phases. Washed with water, washed with saturated brine, anhydrous MgSO 4 Dry and separate by column chromatography to obtain 1.5 g of yellow powder with a yield of 27.6%. 1 H NMR (500MHz CDCl 3 ): δ8.77(d, 1H), 8.63(d, 1H), 8.36(d, 1H), 8.00(d, 1H), 7.87(t, 1H), 7.34(t, 1H). MALDI-TOF MS m / z: 292

Embodiment 3

[0051] Embodiment 3 (synthesis of TPA-BTD-Py)

[0052]

[0053] Under argon protection, 0.763g (1.17mmol) triphenylamine boric acid, 0.18g Pd(PPh 3 ) 4 (0.16mmol), 0.88g (6.37mmol) K 2 CO 3 , 3.16mL H 2 O, 0.463g (1.58mmol) of 4-bromo-7-pyridyl-2,1,3-benzothiadiazole was dissolved by adding 35mL of toluene. To was heated to 125° C. to react overnight, the reaction was stopped, extracted with dichloromethane, and the organic phases were combined. Washed with water, washed with saturated brine, anhydrous MgSO 4 dry. Column chromatography separated 0.55 g of red powder with a yield of 76%. 1 H NMR (500MHz CDCl 3 ): δ8.79(d, 1H), 8.69(d, 1H), 8.52(d, 1H), 7.88(3H), 7.83(d, 1H), 7.33(d, 1H), 7.28(t, 4H) , 7.19(t, 6H), 7.06(t, 2H). MALDI-TOF MS m / z: 456

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Abstract

The invention relates to a fluorescent sensing material with sensing function to phenyl amine compounds, the method and the application thereof. The invention is characterized in that: Aryl is connected with pyridyl to form fluorescent sensing material, the fluorescent sensing material comprises line type, star type and dendritic aryl pyridine; the number of the pyridine units is a positive integer from 1 to 150. The preparation method comprise two steps: synthesizing aryl boric acid or boron ester compound and synthesizing aryl pyridine compound. The fluorescent sensing material provided in the invention is used to detect phenyl amine compounds.

Description

technical field [0001] The invention relates to a fluorescent sensing material capable of sensing aniline compounds, a method and its application in the detection of aniline compounds, belonging to the field of sensing materials for detecting aniline compounds. Background technique [0002] The list of China's environmental pollutants includes 14 categories and 68 kinds of toxic chemical substances, of which aniline compounds (ANI) are one of them and contain a total of 3 substances. Aniline compounds include aniline and its derivatives, dinitroaniline, p-nitroaniline, 2,6-difluoronitroaniline, etc. Such pollutants can cause human poisoning through respiratory tract, skin, eye contact or ingestion. The early symptoms of poisoning are headache, nausea, sometimes vomiting or dry throat. Poisoning at low concentrations (1) can cause reduced oxygen-carrying capacity of the blood (hemoglobinemia), and the skin appears gray-blue and cyanotic. (2) Symptoms of the central nervous ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/02G01N21/64
Inventor 贺庆国何锦龙程建功陈庆曹慧敏
Owner 上海新微科技发展有限公司
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