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Isomeric covalent organic framework material based on tetraphenylbenzene and its preparation method

A technology of covalent organic framework and tetraphenylbenzene, applied in the preparation of organic compounds, organic chemistry, chemical instruments and methods, etc.

Active Publication Date: 2022-03-29
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And so far there is no use of heterogeneous A 2 B 2 Related reports on COFs materials with monomeric structure isomerism

Method used

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  • Isomeric covalent organic framework material based on tetraphenylbenzene and its preparation method
  • Isomeric covalent organic framework material based on tetraphenylbenzene and its preparation method
  • Isomeric covalent organic framework material based on tetraphenylbenzene and its preparation method

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Experimental program
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Effect test

Embodiment 1

[0040] The preparation method of 1,4-bis(4-formylphenyl)-2,5-bis(4-aminophenyl)benzene comprises the steps:

[0041] 1) Weigh 4.0g (8.2mmol) 1,4-dibromo-2,5-diiodobenzene and 3.1g (20.6mmol) 4-formylphenylboronic acid, 0.4g (0.32mmol) tetrakistriphenylphosphine palladium As a catalyst and 4.0g (29.5mmol) potassium carbonate in a 500mL two-necked bottle, put a magnet, add degassed toluene and ethanol (volume ratio 3:1) mixed solvent 160mL and water 1mL, freeze and degas three times, and then in Reaction in an oil bath at 95°C under the protection of argon for 36 hours, after cooling to room temperature, the reaction liquid was concentrated in vacuo, then extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate and spin-dried, and a white solid powder was obtained by column chromatography 1,4-dibromo-2,5-(4-formylphenyl)benzene I (2.5g, yield 69%); (Suzuki coupling reaction catalyzed by palladium catalyst should be protected by inert gas envir...

Embodiment 2

[0047] A method for preparing a heterogeneous covalent organic framework material based on tetraphenylbenzene, comprising the steps of:

[0048]Add 23.5mg (0.05mmol) of p-TPB into a 10mL pressure-resistant tube, then add 1mL of tetrahydrofuran, sonicate for 5 minutes to fully dissolve the solid powder in the solvent, add 0.1mL of 6M acetic acid aqueous solution, and then sonicate for 2min, then freeze and degas three times After the system returns to room temperature, it is placed in an oil bath for reflux reaction for 72 hours. After the reaction, the precipitate is collected by filtration and fully washed with dichloromethane and tetrahydrofuran organic solvents to obtain a light yellow product based on crystallinity and porosity. Isocovalent organic framework material III of tetraphenylbenzene, p-TPB-COF-H for short.

[0049] Its structure is a double-hole structure (double-hole structure means that there are hexagonal channel structure and triangular channel structure in t...

Embodiment 3

[0054] A method for preparing a heterogeneous covalent organic framework material based on tetraphenylbenzene, comprising the steps of:

[0055] Add 23.5mg (0.05mmol) of p-TPB into a 10mL pressure-resistant tube, then add 1mL of n-butanol, sonicate for 5min to fully disperse the solid powder in the solvent, add 0.1mL of 6M acetic acid aqueous solution, sonicate for 2min, then freeze Gas three times, after the system returns to room temperature, put it in an oil bath for reflux reaction for 72h, filter and collect the precipitate after the reaction, and wash thoroughly with dichloromethane and tetrahydrofuran organic solvents to obtain a tetrahydrofuran based tetrahydrofuran compound with excellent crystallinity and porosity. Isocovalent organic framework material IV of phenylbenzene, p-TPB-COF-M for short.

[0056] Its structure is a single-hole structure, (single-hole structure refers to the diamond-shaped channel structure in the structure)

[0057] figure 2 B is the X-ra...

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Abstract

The invention discloses tetraphenylbenzene-based heterogeneous covalent organic framework materials and a preparation method thereof, wherein a tetraphenylbenzene-based heterogeneous covalent organic framework material has formula (III); the tetraphenylbenzene-based heterogeneous organic framework materials of the present invention The iso-covalent organic framework materials p-TPB-COF-H and p-TPB-COF-M of phenylbenzene can be formed from the same monomer 1,4-bis(4-formylphenyl)-2,5-bis( 4‑Aminophenyl)benzene was successfully constructed through the regulation and control of the solvent, which provided a new idea for the design and synthesis of heterogeneous COFs. The heterogeneous covalent organic framework materials based on tetraphenylbenzene of the present invention are used for vitamin B 12 selective adsorption and water vapor adsorption.

Description

technical field [0001] The invention belongs to the field of macromolecular organic porous materials, in particular to tetraphenylbenzene-based heterogeneous covalent organic framework materials p-TPB-COF-H, p-TPB-COF-M and preparation methods. Background technique [0002] Isomerism is a very interesting phenomenon in the field of chemistry, which refers to substances with the same molecular formula but different structures and properties. This phenomenon is common in the fields of drug molecules, porous organic molecular cages, inorganic nanoclusters, and metal-organic frameworks (MOFs), and the properties of these isomers are often quite different. The formation of isomers is related to many factors. Taking metal-organic framework materials as an example, the types of organic ligands, differences in synthesis solvents, changes in metal ions, and differences in synthesis methods may all lead to the appearance of isomers. However, many of these isomers reported so far appe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C223/06C07C221/00C08G73/00
CPCC07C223/06C08G73/00
Inventor 陈龙李玉森
Owner TIANJIN UNIV