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Three-dimensional covalent organic framework materials and synthesis methods based on tetrathiafulvalene units

A covalent organic framework, tetrathiafulvalene technology, applied in separation methods, organic chemistry, chemical instruments and methods, etc., to achieve the effect of high specific surface area

Active Publication Date: 2020-03-31
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In contrast, there are only very few reports on research in the field of 3D COFs materials

Method used

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  • Three-dimensional covalent organic framework materials and synthesis methods based on tetrathiafulvalene units
  • Three-dimensional covalent organic framework materials and synthesis methods based on tetrathiafulvalene units
  • Three-dimensional covalent organic framework materials and synthesis methods based on tetrathiafulvalene units

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 5 mg (0.01 mmol) of tetrahedral configuration tetrakis (4-anilino) adamantane (TAPA) and 6.2 mg (0.01 mmol) tetrakis (p-phenylaldehyde) tetrathiafulvalene (TTF-Ph-CHO) were added Add 1mL of o-dichlorobenzene to the ampoule, mix evenly by ultrasonic, then add 0.1mL (6mol / L) acetic acid aqueous solution, place the ampoule in liquid nitrogen for freezing, vacuumize and seal the tube with flame, after sealing the tube Place in an oven and heat up to 140°C for 5 days. After the reaction, the obtained solid was transferred to a centrifuge tube, washed with N,N-dimethylformamide and tetrahydrofuran for 5 times, heated and vacuum-dried at 80°C for 12 hours, and 7 mg of dark red solid powder COF was obtained. -TTF-Ad, the yield is 70%, and the reaction formula is shown in the following formula.

[0033]

[0034] Such as figure 1 As shown, by comparing the powder X-ray diffraction spectra of the COF-TTF-Ad synthesized in the present invention and the raw material monomer TAP...

Embodiment 2

[0042]5 mg (0.01 mmol) of tetrahedral configuration tetrakis (4-anilino) adamantane (TAPA) and 6.2 mg (0.01 mmol) tetrakis (p-phenylaldehyde) tetrathiafulvalene (TTF-Ph-CHO) were added Add 1mL of o-dichlorobenzene to the ampoule, mix well by ultrasonic, then add 0.1mL (3mol / L) acetic acid aqueous solution, place the ampoule in liquid nitrogen for freezing, vacuumize and seal the tube with flame, after sealing the tube Place in an oven and heat up to 140°C for 5 days. After the reaction, the obtained solid was transferred to a centrifuge tube, washed with N,N-dimethylformamide and tetrahydrofuran for 5 times, heated and vacuum-dried at 80°C for 12 hours to obtain 5 mg of dark red solid powder COF -TTF-Ad, yield 55%. Through the powder X-ray diffraction test, it can be confirmed that a new three-dimensional covalent organic framework material has been successfully synthesized, and its performance test results are as follows: specific surface area: 1245m 2 / g; at a pressure of ...

Embodiment 3

[0044] 5 mg (0.01 mmol) of tetrahedral configuration tetrakis (4-anilino) adamantane (TAPA) and 6.2 mg (0.01 mmol) tetrakis (p-phenylaldehyde) tetrathiafulvalene (TTF-Ph-CHO) were added To the ampoule bottle, add 0.8mL o-dichlorobenzene and 0.2mL mesitylene, ultrasonically mix evenly, then add 0.1mL (6mol / L) acetic acid aqueous solution, place the ampoule bottle in liquid nitrogen for freezing, vacuumize and Seal the tube with flame, place the tube in an oven after sealing, and heat up to 140°C for 5 days. After the reaction, the obtained solid was transferred to a centrifuge tube, washed with N,N-dimethylformamide and tetrahydrofuran for 5 times, heated and vacuum-dried at 80°C for 12 hours to obtain 6.5 mg of dark red solid powder COF-TTF-Ad, yield 65%. Through the powder X-ray diffraction test, it can be confirmed that a new three-dimensional covalent organic framework material has been successfully synthesized, and its performance test results are as follows: specific sur...

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Abstract

The invention discloses a three-dimensional covalent organic framework material based on a tetrathiafulvalene unit and a synthesis method thereof. The material is composed of tetrakis (4-anilino) adamantane and tetrakis (p-phenylaldehyde) tetrathiafulvalene An organic crystal skeleton with a three-dimensional network structure constructed by connecting two monomers through imine bonds, the preparation method of which is: in an organic solvent, four (4-anilino) adamantane and four (p- phenylaldehyde)tetrathiafulvalene is uniformly mixed, and then the catalyst acetic acid aqueous solution is added, and after heating crystallization, solvent washing and heating vacuum drying, the three-dimensional covalent organic framework material COF-TTF-Ad can be obtained. The COF-TTF-Ad material that the inventive method obtains has high specific surface area and regular and ordered microporous structure, and in gas (such as H 2 and CH 4 ) adsorption experiments, showed a large capacity of gas adsorption capacity. Therefore, COF‑TTF‑Ad can be used as an excellent gas adsorption material for gas storage.

Description

technical field [0001] The invention belongs to the field of covalent organic framework materials (COFs), in particular to a three-dimensional covalent organic framework material based on tetrathiafulvalene units and a synthesis method thereof. Background technique [0002] Covalent organic frameworks (COFs) are a new class of crystalline organic framework materials. This type of material has a skeleton structure with open pores, and its chemical composition does not contain metal elements, but only light elements such as H, C, N, B, O, Si, etc. COFs are porous materials that utilize organic building units linked by strong covalent bonds. In terms of material structure, COFs have many advantages, such as: low skeleton density, large specific surface area, regular and ordered pores, controllable physical and chemical properties, easy functionalization, and diversified synthesis strategies. Therefore, COFs materials have shown great application potential in the fields of gas...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D339/06B01J20/22B01J20/28B01J20/30B01D53/02
CPCB01D53/02B01D2257/108B01D2257/7025B01J20/22B01J20/28066B01J20/2809B01J2220/4812C07D339/06Y02C20/20
Inventor 高艳安王宇王畅罗婷
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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