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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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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The currently synthesized anthracycline-containing compounds are mainly organic porous materials, but ionic porous polymers containing anthracyclines have not been reported yet.

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
Comparison scheme
Effect test

Embodiment 1

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

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

[0050]Under argon protection, 9,10-dibromoanthracene (672mg, 2mmol), 4-pyridineboronic acid (615mg, 5mmol), tetrakis (triphenylphosphine) palladium (231mg, 0.2mmol) and potassium carbonate (2.72g , 20mmol) into a 250mL Schlenk bottle. Then 80 mL of DMF solution and 10 mL of water were added successively, and the reaction mixture was placed in an oil bath at 90° C. and stirred at constant temperature for 12 hours. After cooling 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 pH 1 was reached. During acidification, some resid...

Embodiment 2

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

[0065] Under an oxygen atmosphere, AN-POP-1 (2.5-5 μmol, 0.5-1mol%) and 4-methylbenzylamine (0.5mmol) prepared in Example 1 were added to a quartz tube, and then 10 μL of dibromomethane was added, and then Add MeCN (5 mL) to disperse the benzylamine evenly, irradiate with a 26W blue LED light at room temperature, and stir. by TLC and 1 The progress of the reaction was monitored by H NMR, and the reaction was stopped after the disappearance of the starting material. The catalyst was then removed by centrifugation, filtration, and the filtrate was concentrated and evaporated to obtain the crude product. Crude product using 1 HNMR analysis, the ratio of the internal standard and the integrated peak of the product was used to calculate the conversion. Characterization data: 1 H NMR (5...

Embodiment 3

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

[0070] Under an oxygen atmosphere, AN-POP-1 (2.5-5 μmol, 0.5-1mol%) and 4-methoxybenzylamine (0.5mmol) prepared in Example 1 were added to a quartz tube, and then 10 μL of dibromomethane was added, Then MeCN (5 mL) was added to disperse the benzylamine evenly, irradiated with a 26W blue LED light at room temperature, and stirred. by TLC and 1 The progress of the reaction was monitored by H NMR, and the reaction was stopped after the disappearance of the starting material. The catalyst was then removed by centrifugation, filtration, and the filtrate was concentrated and evaporated to obtain the crude product. Crude product using 1 HNMR analysis, the ratio of the internal standard and the integrated peak of the product was used to calculate the conversion. Characterization data: 1 H...

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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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