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Organic microporous material with metal coordination containing heteroatoms and preparation and application thereof

A technology of microporous materials and metal coordination, applied in metal coordination heteroatom-containing organic microporous materials and their preparation and application fields, can solve problems such as poor thermal stability, and achieve uniform pore size, uniform pore size distribution, and large nitrogen adsorption. amount of effect

Active Publication Date: 2019-01-04
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such materials are composed of weak coordination bonds, so their thermal stability is relatively poor, and they are relatively sensitive to acids, alkalis, air, water vapor, etc.

Method used

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  • Organic microporous material with metal coordination containing heteroatoms and preparation and application thereof
  • Organic microporous material with metal coordination containing heteroatoms and preparation and application thereof
  • Organic microporous material with metal coordination containing heteroatoms and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Preparation of compound 3:

[0047] Under argon protection, add PdCl to a dry two-necked flask equipped with magnetic stirring 2 (PPh 3 ) 2 (1.71g, 2.44mmol), cuprous iodide (0.77g, 4mmol), 2-bromo-4-iodopyridine (11.5g, 40.4mmol) and 50mL of triethylamine, stirred in an oil bath at 50°C, and Add trimethylsilylacetylene (5.68mL, 40.4mmol) into the reaction vial with a syringe, react at this temperature for 24 hours, TLC traces the completion of the reaction, and stops the reaction. Cool to room temperature, wash with water, salt, anhydrous MgSO 4 After drying and suction filtration, the solvent was distilled off, dissolved in dichloromethane, and separated and purified by column chromatography (stationary phase: silica gel; developer: dichloromethane:petroleum ether=1:2) to obtain 5.52 g of a colorless liquid. Yield 75%.

[0048] 1 H NMR (400MHz, CDCl 3 )δ8.31(d,J=5.1Hz,1H),7.52(s,1H),7.25(d,J=5.0Hz,1H),0.26(s,9H). 13 C NMR (101MHz, CDCl 3 )δ150.32, 142.81, 134...

Embodiment 2

[0050] Preparation of compounds 4 and 5:

[0051] Under argon protection, add compound 3 (5.52g, 30.33mmol), tetrabutylammonium fluoride (7.93g, 30.33mmol), and 50mL of newly distilled tetrahydrofuran solution into a 100mL two-necked flask, and stir for 30 minutes at room temperature ; Then add 10mL saturated NH 4 Cl solution and continued to stir for 5 minutes. Stop the reaction, evaporate the solvent, dichloromethane extraction, anhydrous MgSO 4 After drying and suction filtration, the solvent was distilled off to obtain compound 4 as a colorless oil. Since compound 4 was unstable, it was directly reacted in the next step. In a two-necked flask containing colorless oily compound 4, add 2-bromo-4-iodopyridine (8.61g, 30.33mmol), PdCl 2 (PPh 3 ) 2 (2.08g, 1.82mmol), cuprous iodide (3.48g, 3.03mmol), triethylamine (50mL). Stir in an oil bath at 50° C., react for 24 hours, and stop the reaction after tracking the completion of the reaction by TLC. After cooling to room te...

Embodiment 3

[0054] Preparation of Compound 6:

[0055] Under argon protection, into a 100mL two-necked flask, add compound 5 (7.38g, 21.83mmol), 2-thiophene boronic acid (5.58g, 43.66mmol), Pd(PPh 3 ) 4 (1.50 g, 1.31 mmol), potassium carbonate in THF (2M, 30 mL) was added. Heated to reflux, reacted for 24 hours, TLC tracked that the reaction was complete, and stopped the reaction. After cooling to room temperature, the mixture was extracted with dichloromethane (70mL×3), the organic layer was washed with water (50mL×3), anhydrous MgSO 4 dry. The solvent was distilled off, dichloromethane was dissolved, and then separated and purified by column chromatography (eluent: dichloromethane) to obtain 5.85 g of white solid with a yield of 78%.

[0056] 1 H NMR (400MHz, CDCl 3 )δ8.61(d, J=5.0Hz, 2H), 7.80(s, 2H), 7.67(d, J=3.1Hz, 2H), 7.46(d, J=5.0Hz, 2H), 7.30-7.26( m,2H),7.15(t,J=4.3Hz,2H). 13 C NMR (101MHz, CDCl 3 )δ149.57, 145.24, 138.19, 134.19, 129.03, 127.41, 125.63, 123.79, 118.64...

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Abstract

The invention relates to an organic microporous material with metal coordination containing heteroatoms and preparation and application thereof. An organic conjugated precursor of the organic microporous material has a structural formula of I or II. The preparation comprises the steps of preparation of 4-trimethylsilylacetylene-2-bromopyridine or 5-trimethylsilylacetylene-3-bromopyridine, preparation of 4-ethynyl-2-bromopyridine or 5-ethynyl-3-bromopyridine, preparation of bis(2-bromopyridine) acetylene or bis(3-bromopyridine) acetylene, preparation of bis(2-thiophene pyridine) acetylene or bis(3-thiophene pyridine) acetylene, preparation of the organic conjugated precursor, and preparation of the organic microporous material with the metal coordination containing the heteroatoms. The organic microporous material has a controllable form and structure, thereby having different properties and functions, and can be applied to the development of novel functional materials such as gas adsorption and storage, molecular separation, catalysis, sustained release of drugs and the like.

Description

technical field [0001] The invention belongs to the field of organic microporous materials and their preparation and application, in particular to a metal-coordinated heteroatom-containing organic microporous material and its preparation and application. Background technique [0002] Supramolecular materials chemistry has become an important development direction of current chemistry. Due to the potential application value of conjugated organic systems in nonlinear luminescent materials, catalytic materials, adsorption and separation materials, and organic microporous materials, the morphology-controllable autonomous assembly formed by conjugated organic terminal heteroatom precursors and transition metals Supramolecular materials have become a new hot spot for researchers. [0003] Conjugated microporous polymers (CMPs) have broad application prospects due to their electronic and electroluminescent properties. Most of the conjugated systems themselves have a relatively rig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00
CPCC08G83/008
Inventor 金武松于秋影张灯青李贤英
Owner DONGHUA UNIV
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