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Chiral catalyst (S)-DTP-COF and preparation method, recycling method and application thereof

A -DTP-COF, chiral catalyst technology, applied in catalytic reactions, chemical instruments and methods, preparation of organic compounds, etc., to achieve the effects of reducing costs, improving utilization, and easy recovery

Active Publication Date: 2020-11-24
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the inventors found that so far, there are very few reports on chiral COFs, so the development of strategies to construct chiral COFs is an important and challenging topic in this field.

Method used

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  • Chiral catalyst (S)-DTP-COF and preparation method, recycling method and application thereof
  • Chiral catalyst (S)-DTP-COF and preparation method, recycling method and application thereof
  • Chiral catalyst (S)-DTP-COF and preparation method, recycling method and application thereof

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Experimental program
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preparation example Construction

[0024] A preparation method for chiral catalyst S-T-CCOF, the preparation steps are:

[0025] Place cuprous trifluoromethanesulfonate and (S,S)-2,6-bis(4-phenyl-2-oxazolin-2-yl)pyridine in a round-bottomed flask with chloroform as solvent, stirring dissolve. Add 2,5-dimethoxybenzene-1,4-dicarbaldehyde, 1,3,5-tris(4-aminophenyl)benzene, and phenylacetylene into a round-bottomed flask, and stir at room temperature for 48 hours. Finally, add acetic acid and stir for 24-48h to obtain (S)-DTP-COF.

[0026] In some embodiments, the cuprous trifluoromethanesulfonate, (S,S)-2,6-bis(4-phenyl-2-oxazolin-2-yl)pyridine, 2,5-bis The molar ratio of methoxybenzene-1,4-dicarbaldehyde, 1,3,5-tris(4-aminophenyl)benzene and phenylacetylene is 1:1:9:6:3.7 to improve reaction efficiency and yield .

[0027] Preferably, the amount of the chloroform solvent is 25mL to effectively dissolve cuprous trifluoromethanesulfonate, (S, S)-2,6-bis(4-phenyl-2-oxazolin-2-yl) pyridine.

[0028] Preferably,...

Embodiment 1

[0037] Embodiment 1: the synthesis of (S)-DTP-COF

[0038] Put 12mg (0.02mmoL) of cuprous trifluoromethanesulfonate, 8mg (0.02mmoL) of (S, S)-2,6-bis(4-phenyl-2-oxazolin-2-yl)pyridine in 50ml In a round bottom flask, add 25ml of chloroform and stir to dissolve. 38.40mg (0.198mmoL) 2,5-dimethoxybenzene-1,4-dicarbaldehyde, 43mg (0.122mmoL) 1,3,5-three (4-aminophenyl) benzene, 90μl (0.819mmoL) Phenylacetylene was added to the round bottom flask and stirred at room temperature for 48h. Finally, 15μl of acetic acid was added and stirred for 24-48h. After the reaction was completed, centrifuged, washed 3 times with chloroform, and then washed 3 times with ethanol to obtain (S)-DTP-COF.

[0039] We characterized the polymer by IR, PXRD, CD spectra, the results are shown in figure 1 , 2 , 3.

[0040]

Embodiment 2

[0042] 1 ml (10 mmol) cyclohexanone, 344.4 mg (20% mol) pTsOH, EtOH (2 mL), 5 mg (3.3 mol%) (S)-DTP-COF were stirred at 25 °C for 10 minutes. Then (0.5 mmol) nitroalkene was added and the mixture was stirred at 25°C for 48 hours. After the reaction was finished, the reaction system was lowered to room temperature, and the catalyst was filtered out by centrifugation. After the solvent was removed by rotary evaporation, the product was purified through a silica gel column to obtain the corresponding product. Recover the catalyst, put it into the next reaction, directly separate and calculate the yield, the catalytic effect is as follows Figure 4 shown.

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Abstract

The invention belongs to the technical field of catalyst preparation and particularly relates to a chiral catalyst (S)-DTP-COF and a preparation method and application thereof. The preparation methodof the chiral catalyst (S)-DTP-COF comprises the steps of: putting cuprous triflate and (S,S)-2,6-bis(4-phenyl-2-oxazolyl-2-yl)pyridine into a round-bottom flask, taking chloroform as a solvent, and carrying out stirring and dissolving; adding 2,5-dimethoxyterephthalaldehyde, 1,3,5-tris(4-aminophenyl)benzene and phenylacetylene into the round-bottom flask and stirring at room temperature for 48 hours; and finally adding an acetic acid and carrying out stirring for 24-48 hours to obtain (S)-DTP-COF. The catalyst can effectively catalyze Michael addition reaction, high temperature is not needed,the amount of the catalyst is small, no other additives are used, and heterogeneous catalysis can be achieved. Meanwhile, the catalyst can be reused and easily recycled, so that the utilization rateof the catalyst is improved, the cost is reduced and industrial popularization and application are facilitated.

Description

technical field [0001] The invention belongs to the technical field of catalyst preparation, and in particular relates to a chiral catalyst, (S)-DTP-COF and its preparation method and application. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Current research on chiral science and technology covers the preparation of chiral compounds such as pharmaceuticals and fine chemicals, as well as the fields of sensing, magnets, molecular switches and optical devices. In recent years, chiral materials have aroused widespread interest because of their applications in the chiral field and their ability to be recycled. At the same time, people's demand for chiral materials is also ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/02B01J31/06C07C201/12C07C205/45
CPCC08G73/02B01J31/06C07C201/12B01J2231/32C07C205/45
Inventor 董育斌阚璇王建成尚金燕乔华
Owner SHANDONG NORMAL UNIV
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