Preparation and catalytic application of donor-acceptor type ionic porous polymer

A technology of porous polymers and donors, applied in the direction of imino compound preparation, catalytic reaction, organic compound/hydride/coordination complex catalyst, etc., to achieve the effect of mild reaction conditions, stable structure and high yield

Active Publication Date: 2020-11-24
DALIAN UNIV OF TECH
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

The currently synthesized anthracycline-containing compounds are mainly organic porous m

Method used

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  • Preparation and catalytic application of donor-acceptor type ionic porous polymer
  • Preparation and catalytic application of donor-acceptor type ionic porous polymer
  • Preparation and catalytic application of donor-acceptor type ionic porous polymer

Examples

Experimental program
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Example Embodiment

[0047] Example 1

[0048] A preparation method of donor-acceptor ionic porous polymer iPOPs (AN-POP-1) containing anthracene rings, the steps are as follows:

[0049] (1) Preparation of compound A: 9,10-bis(3-pyridyl)anthracene;

[0050] Under the protection of argon, 9,10-dibromoanthracene (672mg, 2mmol), 4-pyridineboronic acid (615mg, 5mmol), tetrakis(triphenylphosphine) palladium (231mg, 0.2mmol) and potassium carbonate (2.72g) , 20mmol) was added to a 250mL Schlenk bottle. Then, 80 mL of DMF solution and 10 mL of water were sequentially added, and the reaction mixture was placed in an oil bath at 90° C. and stirred at constant temperature for 12 hours. After the reaction, it was cooled to room temperature, the solvent was removed in vacuo, and the residue was redissolved in a mixture of chloroform and water. The two phases were separated, and the organic layer was washed twice with water. Finally, hydrochloric acid (1M) was added to the collected aqueous phase until the pH re...

Example Embodiment

[0063] Example 2

[0064] The test method for the amine oxide coupling reaction catalyzed by the donor-acceptor ionic porous polymer iPOPs (AN-POP-1) containing anthracycline prepared in Example 1 is as follows:

[0065] In an oxygen atmosphere, the AN-POP-1 (2.5-5μmol, 0.5-1mol%) and 4-methylbenzylamine (0.5mmol) prepared in Example 1 were added to the quartz tube, and then 10μL of dibromomethane was added, and then MeCN (5 mL) was added to disperse the benzylamine uniformly, irradiated with a 26W blue LED light at room temperature, and stirred. Through TLC and 1 H NMR monitors the progress of the reaction, and stops the reaction after the raw material disappears. Then the catalyst is removed by centrifugation and filtration, and the filtrate is concentrated and evaporated to obtain a crude product. Crude product use 1 In HNMR analysis, the ratio of the internal standard to the integrated peak of the product is used to calculate the conversion rate. Characterization data: 1 H N...

Example Embodiment

[0068] Example 3

[0069] The test method for the amine oxide coupling reaction catalyzed by the donor-acceptor ionic porous polymer iPOPs (AN-POP-1) containing anthracycline prepared in Example 1 is as follows:

[0070] In an oxygen atmosphere, add AN-POP-1 (2.5-5 μmol, 0.5-1 mol%) and 4-methoxybenzylamine (0.5 mmol) prepared in Example 1 into a quartz tube, and then add 10 μL of dibromomethane, Then, MeCN (5 mL) was added to disperse the benzylamine uniformly, irradiated with a 26W blue LED lamp at room temperature, and stirred. Through TLC and 1 H NMR monitors the progress of the reaction, and stops the reaction after the raw material disappears. Then the catalyst is removed by centrifugation and filtration, and the filtrate is concentrated and evaporated to obtain a crude product. Crude product use 1 In HNMR analysis, the ratio of the internal standard to the integrated peak of the product was used to calculate the conversion rate. Characterization data: 1 H NMR(500MHz, CDCl...

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Abstract

The invention belongs to the technical field of fine chemical engineering, and discloses preparation and catalytic application of a donor-acceptor type ionic porous polymer. The polymer AN-POP-1 is prepared through a Zincke reaction. An anthracene ring structure is introduced into 1,1'-bis(2,4-dinitrophenyl)-[9,10-bis(3-pyridyl)anthracene]-1,1'-diammonium dichloride, so that the photocatalytic performance is improved; the preparation method comprises the following steps: adding 1,1'-bis(2,4-dinitrophenyl)-[9,10-bis(3-pyridyl)anthracene]-1,1'-diammonium dichloride and 1,3,5-tri(4-aminophenyl)triazine C into a schlenk tube, and reacting for 48-72 hours under the protection of nitrogen at 100-150 DEG C to obtain the polymer AN-POP-1 catalyst. The AN-POP-1 polymer prepared by the invention hasgood chemical and thermal stability and relatively high catalytic performance, and the catalytic yield of a benzylamine derivative can reach 90% or above.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to the preparation of a donor-acceptor type ion porous polymer and its catalytic application. Background technique [0002] In recent years, the rapid development of modern industrialization and the development and utilization of a large number of fossil fuels have caused serious energy crises and environmental pollution, which have made human beings face serious challenges to survival. Finding, developing and utilizing new green energy has become the current scientific research focus. One of the hot topics. As a green, non-polluting and inexhaustible energy source, solar energy has become an effective way to solve energy and environmental problems by converting low-density solar energy into high-density chemical energy or directly mineralizing organic pollutants through photocatalytic technology. The core issue in the field of photocatalysis is to develop efficient, stable ...

Claims

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Application Information

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IPC IPC(8): C08G61/12B01J31/06C07C249/02C07C251/24
CPCC08G61/122B01J31/06C07C249/02C08G2261/43C08G2261/3221B01J2231/70C07C251/24
Inventor 贡卫涛曲卫东
Owner DALIAN UNIV OF TECH
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