Nitroxide free radical functionalized three-dimensional covalent organic framework material and preparation method thereof

A technology of covalent organic framework and nitroxide free radicals, which is applied in the field of synthesis of three-dimensional covalent organic framework materials, can solve problems such as difficulties in the synthesis of three-dimensional covalent organic framework materials, and achieve the effect of avoiding damage

Inactive Publication Date: 2020-06-19
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to overcome the difficulties in the synthesis of functionalized three-dimensional covalent organic framework materials in the prior art, the present invention first synthesized an aldehyde derivative with a TEMPO functional group, and then successfully synthesized a nitrogen 3D COFs of Oxygen Radicals (TEMPO), named JUC-700

Method used

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  • Nitroxide free radical functionalized three-dimensional covalent organic framework material and preparation method thereof
  • Nitroxide free radical functionalized three-dimensional covalent organic framework material and preparation method thereof
  • Nitroxide free radical functionalized three-dimensional covalent organic framework material and preparation method thereof

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Embodiment 1

[0036] A three-dimensional covalent organic framework material functionalized with nitroxide free radicals (TEMPO), which is composed of 4,7-bis(4-formylphenyl)-2,2,6,6-tetramethylpiperidine-N -Oxygen free radicals and tetrakis (4-aminophenyl) methane form the organic framework structure by Schiff base reaction, and its structural formula is as follows:

[0037]

[0038] Further, the chemical structural formula of the 4,7-bis(4-formylphenyl)-2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO-TPDA) is as follows :

[0039]

[0040] A preparation method of a three-dimensional covalent organic framework material functionalized by nitroxide free radicals (TEMPO), the specific steps are as follows:

[0041] (1) Synthesis of 4,7-bis(4-bromophenyl)-2,2,6,6-tetramethylpiperidine-N-oxyl radical:

[0042]

[0043] Dissolve 2,5-dibromobenzoic acid (8.06g) in 32mL of thionyl chloride, reflux at 80°C for 3h, cool to room temperature after the reaction, and spin dry to remove th...

Embodiment 2

[0055] Step (1), (2) are with embodiment 1,

[0056] (3) Tetrakis(4-phenylamino)methane (TAPM, (15mg) and 4,7-bis(4-formylphenyl)-2,2,6,6-tetramethylpiperidine-N-oxygen Free radicals (TEMPO-TPDA, 35.5mg) were thoroughly mixed in a mortar and then added to a glass tube, then slowly added 0.5mL 1,2-o-dichlorobenzene, 0.75mL 1-butanol, 0.1ml acetic acid (3mol / L), inflated three times under the nitrogen atmosphere, then the glass tube is placed in the freezing reaction system in liquid nitrogen, and then the glass tube is blocked under the flame of methane / oxygen. The prepared glass tube reaction system is placed in 120 ℃ oven for 5 days. After the reaction is over, open the glass tube with a glass cutter, wash the product with N,N-dimethylformamide and acetone three times, and then filter it. The solid product is vacuum-dried at 80°C After drying in the oven for 2 hours, a tan target product was obtained with a yield of 80%. Subsequent characterization was carried out after soa...

Embodiment 3

[0058] Tetrakis(4-anilino)methane (TAPM, (15 mg) and 4,7-bis(4-formylphenyl)-2,2,6,6-tetramethylpiperidine-N-oxyl radical ( TEMPO-TPDA, 35.5mg) was mixed thoroughly in a mortar and then added to a glass tube, then slowly added 0.5mL 1,2-o-dichlorobenzene, 0.75mL 1-butanol, 0.1ml acetic acid (4mol / L) , pump and inflate three times under a nitrogen atmosphere, then place the glass tube in liquid nitrogen to freeze the reaction system, and then seal the glass tube under a methane / oxygen flame. Place the prepared glass tube reaction system in an oven at 140°C 3 days. After the reaction is over, open the glass tube with a glass cutter, wash the product three times with N,N-dimethylformamide and acetone, and then filter. Dry the solid product in a vacuum oven at 80°C After 2 hours, the brown-colored target product was obtained with a yield of 79%.

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Abstract

The invention discloses a nitroxide free radical functionalized three-dimensional covalent organic framework material and a preparation method thereof. The invention belongs to the field of functionalized three-dimensional covalent organic frame (3D COFs) materials. The method comprises the following steps: firstly, preparing 2,7-bis(4-formylphenyl)-2, 2, 6, 6-tetramethylpiperidine-N-oxygen free radical (TEMPO-TPDA) containing a TEMPO functional group, and constructing a TEMPO functionalized three-dimensional covalent organic framework material (JUC-700) from the 2,7-bis (4-formylphenyl)-2, 2,6, 6-tetramethylpiperidine-N-oxygen free radical (TEMPO-TPDA) as a construction unit and tetra(4-aminophenyl)methane by a Schiff base reaction. According to the present invention, the PXRD determination results show that the obtained material has good crystallinity, and the EPR characterization further proves that TEMPO stably exists in the material.

Description

technical field [0001] The invention belongs to the field of functionalized three-dimensional covalent organic framework (3D COFs) framework materials, and in particular relates to the synthesis of a three-dimensional covalent organic framework material functionalized by nitroxide free radicals (TEMPO). Background technique [0002] Covalent organic frameworks (COFs) are a new type of crystalline organic porous polymers, which are mainly formed by reversible reactions of various organic building units. Since COFs were first reported by Yaghi's research group in 2005, they have received extensive attention from material scientists. It can be said that the emergence of COFs materials is a milestone in the development of crystalline organic porous materials. The constituent elements of covalent organic frameworks (COFs) are some light elements such as (C, H, O, N, and B), so they have high specific surface area and low density, and have potential applications in gas storage. C...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00
CPCC08G83/008
Inventor 方千荣常建红李辉
Owner JILIN UNIV
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