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Functionalized tripillar[5]arene compound and synthesis and application thereof

An aromatic hydrocarbon compound, functionalized technology, applied in chemical instruments and methods, organic chemistry, other chemical processes, etc., can solve the problems of no specific antidote, high mortality, and high human toxicity.

Inactive Publication Date: 2020-02-04
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Paraquat is extremely toxic to humans, and there is no specific antidote, and the mortality rate of oral poisoning is extremely high

Method used

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  • Functionalized tripillar[5]arene compound and synthesis and application thereof
  • Functionalized tripillar[5]arene compound and synthesis and application thereof
  • Functionalized tripillar[5]arene compound and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthesis of embodiment 1, TP2-I

[0034] Put 0.1 g (0.1 mmol) of hydrazine hydrate functionalized column[5]arene (TP2) in a 100 mL round bottom flask, add 50 mL of DMF as solvent, slowly add 0.18 g (2 mmol) of p-hydroxybenzaldehyde functionalized under stirring Column [5] arene I, and add 1mL of glacial acetic acid as a catalyst, heat to 140°C on an oil bath and reflux for 72h. After the reaction stopped, it was cooled to room temperature, filtered with suction, mixed with silica gel, spin-dried, and purified by column chromatography (petroleum ether: ethyl acetate = 20:1). The light yellow product obtained was TP2-I. Yield: 21%.

[0035] TP2-I: (m.p. greater than 133℃), 1 H NNR (600 MHZ, d 6 -DMSO), δ / ppm: 11.27 (s,2H),8.13 (s,1H), 7.93 (s,2H), 7.61 (m, 3H),6.96 (m, 4H), 6.78 (m, 30H), 4.00 (m, 12H), 3.64 (s, 108H), 3.30 (s, 4H), 2.71 (s, 4H), 1.86 (m, 16H).

Embodiment 2

[0036] Embodiment 2, TP2-I adsorption removes methyl viologen in the water sample

[0037] Pipette the solid of 1mg TP2-I and place it in a colorimetric tube, then take the aqueous solution of methyl viologen (1×10 -4 mol L -1 ) 5ml was stirred on a magnetic stirrer in a 10ml centrifuge tube, and the clear liquid was taken every five minutes to measure the absorbance. until the absorbance remains constant. Determine the residual concentration of methyl viologen after adsorption. By calculation, the adsorption rate of the compound to methyl viologen was 91.2%.

Embodiment 3

[0038] Embodiment 3, TP2-1 detects the concentration of methyl viologen in the water sample

[0039] Preparation of sample solution: take a certain amount of methyl viologen, and prepare it with water to a concentration of 1×10 -4 mol L -1 aqueous solution;

[0040] Detection of the concentration of methyl viologen: pipette 1 mg of the main body TP2-I solid and place it in a colorimetric tube; take a sample solution containing methyl viologen (1×10 -4 mol L -1 ) 5ml into a colorimetric tube, stirred on a magnetic stirrer, and the clear solution was taken every five minutes to measure the absorbance until the absorbance remained unchanged. Calculate the residual concentration of methyl viologen according to the linear relationship between the ultraviolet absorbance of the main TP2-I solution and the concentration of methyl viologen, which is 8.87×10 -5 mol L -1 , the concentration of methyl viologen adsorbed by the adsorbent is 1.12×10 -5 mol L -1 . The sum of the ads...

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Abstract

The invention discloses a functionalized tripillar[5]arene compound preparation method. A functionalized tripillar[5]arene compound is obtained in the mode that hydrazine hydrate functionalized pillar[5]arene and p-hydroxy benzaldehyde functionalized pillar[5]arene react in DMF, and then separation and purifying are conducted. Through nuclear magnetic titration experiments, it is shown that the prepared functionalized tripillar[5]arene compound is complexed with methyl viologen in d6-DMSO, thus adsorption to the methyl viologen by the functionalized tripillar[5]arene compound is achieved, therefore, the methyl viologen in the environment is removed in an adsorption mode, and the adsorption rate reaches 91.2%. Through an ultraviolet absorption spectrum, it is shown that within the concentration range of 2*10<-3> mmol / L to 2*10<-2> mmol / L, a linear relation is formed between the ultraviolet absorbancy degree of a functionalized tripillar[5]arene compound solution and the concentration ofthe methyl viologen, and thus the content of the methyl viologen in water samples is monitored quantitatively.

Description

technical field [0001] The present invention relates to a bisacylhydrazone functionalized column [5] arene, in particular to a hydrazine hydrate functionalized column [5] arene, p-hydroxybenzaldehyde functionalized column [5] arene, and the present invention also relates to a bisacylhydrazone function The invention relates to single-selective fluorescence recognition of methyl viologen in a solution of a columnar [5] aromatic hydrocarbon, and belongs to the field of supramolecular organic scientific research. Background technique [0002] With the development of society, people use more and more pesticides, so there are various problems, such as pollution to the environment, and the harm of pesticides to the human body. Therefore, it is very necessary to achieve the degradation or adsorption of residual pesticides. Methyl viologen (BCK), also known as paraquat, is a fast-killing herbicide, which has a contact effect and a certain systemic effect, and can be quickly absorbed...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/52C07C319/20C09K11/06G01N21/64B01J20/22
CPCB01J20/22C07C319/20C07C323/52C09K11/06C09K2211/1011C09K2211/1014C07C2603/92G01N21/643G01N2021/6432
Inventor 林奇王中会孙小文魏太保张有明姚虹
Owner NORTHWEST NORMAL UNIVERSITY
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