Metal-organic framework material with hydrogen bond catalytic activity, and preparation method and application thereof

A catalytic activity, organic framework technology, applied in the preparation of organic compounds, catalytic reactions, organic compounds/hydrides/coordination complex catalysts, etc. , inactivation and other problems, to achieve the effect of low price, good size selectivity and reproducibility, and low cost

Active Publication Date: 2019-11-12
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 1. Aromatic amine derivatives are prone to self-aggregation or oligomer formation due to their strong hydrogen bonding and inactivation;
[0005] 2. Aromatic amine derivatives cannot be recycled in a homogeneous catalytic system

Method used

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  • Metal-organic framework material with hydrogen bond catalytic activity, and preparation method and application thereof
  • Metal-organic framework material with hydrogen bond catalytic activity, and preparation method and application thereof
  • Metal-organic framework material with hydrogen bond catalytic activity, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Weigh 0.1mmol 3,3'-((3,4-dioxocyclobut-1-ene-1,2-diyl)bis(imino))dibenzoic acid (H 2 dbda) and 0.4mmol Zn(NO 3 ) 2 ·6H 2 0, placed in a 10mL glass sample bottle, add 5mL of ethanol and DMF (volume ratio is 1:4) mixed solvent, then the glass sample bottle is placed in the hydrothermal synthesis reaction kettle, and then the reaction kettle is placed on the electric heating drum In an air drying oven, keep the temperature at 80°C and react for 24 hours. After the reaction is over, cool down to obtain a light yellow blocky crystal, then filter, wash with ethanol, and dry at 100°C for 9 hours to prepare the metal-organic framework material Zn-DBDA. The yield is: 85%. Its crystal structure is as figure 1 As shown, it can be seen from the figure that there are two groups of aromatic amine groups with different orientations in each independent channel, which provide potential hydrogen bonding sites for the activation of substrates through hydrogen bonding.

[0041] Cataly...

Embodiment 2

[0054] Weigh 0.1mmol 3,3'-((3,4-dioxocyclobut-1-ene-1,2-diyl)bis(imino))dibenzoic acid (H 2 dbda) and 0.38mmol Zn(NO 3 ) 2 ·6H 2 0, placed in a 10mL glass sample bottle, add 5mL of ethanol and DMF (volume ratio is 1:4) mixed solvent, then the glass sample bottle is placed in the hydrothermal synthesis reaction kettle, and then the reaction kettle is placed on the electric heating drum In an air drying oven, keep a constant temperature of 75°C and react for 22 hours. After the reaction is completed, cool down to obtain a light yellow blocky crystal, then filter, wash with ethanol, and dry at 95°C for 10 hours to prepare the metal-organic framework material Zn-DBDA. The yield is: 82%. Its crystal structure and catalytic performance are the same as in Example 1.

Embodiment 3

[0056] Weigh 0.1mmol 3,3'-((3,4-dioxocyclobut-1-ene-1,2-diyl)bis(imino))dibenzoic acid (H 2 dbda) and 0.42mmol Zn(NO 3 ) 2 ·6H 2 0, placed in the glass sample vial of 10mL, add the mixed solvent of 5.2mL ethanol and DMF (volume ratio is 1:4.2), then the glass sample vial is placed in the hydrothermal synthesis reactor, then the reactor is placed on the electric heater In a blast drying oven, keep a constant temperature of 80°C and react for 24 hours. After the reaction is over, cool down to obtain a light yellow blocky crystal, then filter, wash with ethanol, and dry at 100°C for 8 hours to obtain the metal-organic framework material Zn–DBDA. The yield : 84%. Its crystal structure and catalytic performance are the same as in Example 1.

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Abstract

The invention discloses a metal-organic framework material with hydrogen bond catalytic activity and a preparation method and an application thereof. The metal-organic framework material is prepared by taking a metal ion Zn<2+> as a node and 3,3'-((3,4-dioxocyclobutyl-1-ene-1,2-diyl)bisimino)dibenzoic acid as an organic connecting ligand through a solvothermal reaction. The chemical formula of thematerial is [Mm(OH)(L)n.(DMF)q]; in the formula, L is the 3,3'-((3,4-dioxocyclobutyl-1-ene-1,2-diyl)bisimino)dibenzoic acid, M is a metal ion Zn<2+>, DMF is N,N-dimethylformamide, m = 1.5, n = 1, q =2. The material provided by the invention has efficient performance of catalyzing the addition reaction of a 1,3-dicarbonyl compound and nitroolefin under mild conditions, and has a bifunctional hydrogen bond donor-receptor catalytic activation center, size selectivity and cycling stability. The preparation process is simple, environment-friendly, low in cost and easy for large-scale preparation.

Description

technical field [0001] The invention belongs to the field of catalytic materials and relates to a metal-organic framework material, in particular to a metal-organic framework material with hydrogen bond catalytic activity and its preparation method and application. Background technique [0002] Inspired by synthetic reactions in nature, synthetic chemists have long attempted to construct effective abiotic platforms to mimic biological systems with high synthetic selectivity and high efficiency. This is because of the potential to develop catalysts that match or even exceed the catalytic activity of natural systems. Considering the critical role of hydrogen bonding in countless natural processes, hydrogen-bonding (HB) organocatalysis has emerged as a biomimetic alternative to enzymatic catalysis, which can activate electrophilic moieties via cooperative hydrogen bonding for nucleophilic addition. [0003] Aromatic amine derivatives have the characteristics of the integration...

Claims

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Application Information

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IPC IPC(8): C08G83/00B01J31/22C07C201/12C07C205/45C07C205/53
CPCB01J31/1691B01J31/2208B01J2231/32B01J2531/0213B01J2531/26C07C201/12C08G83/008C07C205/45C07C205/53
Inventor 王健赵晓利李博文张娜武鹏彦
Owner XUZHOU NORMAL UNIVERSITY
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