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A carbon-carbon double bond bridged all-carbon skeleton two-dimensional conjugated organic framework material and its preparation method

An organic framework, carbon-carbon double bond technology, applied in the preparation of organic compounds, organic chemistry, carboxylate preparation and other directions, to achieve uniform pore structure and semiconductor properties, high crystallinity, high specific surface area effects

Active Publication Date: 2021-09-24
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, it is urgent and challenging to find more core monomers to synthesize such COF materials.

Method used

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  • A carbon-carbon double bond bridged all-carbon skeleton two-dimensional conjugated organic framework material and its preparation method
  • A carbon-carbon double bond bridged all-carbon skeleton two-dimensional conjugated organic framework material and its preparation method
  • A carbon-carbon double bond bridged all-carbon skeleton two-dimensional conjugated organic framework material and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Such as figure 1 As shown, in an argon atmosphere glove box, 39mg 2,4,6-tricyano-1,3,5-mesitylene, 86mg 4,4"-diformyl-p-terphenyl (or 63mg 4,4'-diformyl-1,1'-biphenyl, or 78mg 1,3,5-tris(4-formylphenyl)benzene), 102mg anhydrous piperidine, 5mL anhydrous N,N -Add dimethylformamide and 5mL o-dichlorobenzene into a 15m thick-walled pressure-resistant bottle. Seal the thick-walled pressure-resistant bottle with a polytetrafluoroethylene screw plug, transfer it to a constant temperature oil bath, and heat to 120°C Reaction for 72 hours. After the reaction, the reaction bottle was naturally cooled to room temperature, and the filter residue was collected by vacuum filtration, rinsed with tetrahydrofuran, acetone, methanol and dichloromethane respectively, and the product was collected and vacuum-dried at 60°C for 12 hours to obtain orange Solid.The three products were named as COF-p-3Ph, COF-p-2Ph and COF-m-3Ph.

[0036] Such as figure 2As shown, the powder X-ray diffract...

Embodiment 2

[0042] In a glove box under an argon atmosphere, 39 mg of 2,4,6-tricyano-1,3,5-mesitylene, 86 mg of 4,4"-diformyl-p-terphenyl, 102 mg of anhydrous piperidine Pyridine, 5mL of anhydrous N,N-dimethylformamide and 5mL of o-dichlorobenzene were added to a 15mL thick-walled pressure-resistant bottle. Seal the thick-walled pressure-resistant bottle with a Teflon screw plug and transfer it to a constant temperature oil In a bath, heat to 120 ° C for 72 hours. After the reaction, the reaction bottle is naturally cooled to room temperature, and the filter residue is collected by vacuum filtration, rinsed with tetrahydrofuran, acetone, methanol and dichloromethane respectively, and the product is collected and stored at 60 °C and vacuum dried for 12 hours to obtain an orange solid. The product was named COF-p-3Ph.

[0043] Add 1.0mmol 4-carboxyphenylboronic acid, 5mg COF-p-3Ph, 3.0mmol triethylamine, 5.0mL acetonitrile and a magnetic stir bar into a 10mL glass tube. Submerge the reacti...

Embodiment 3

[0045] In a glove box under an argon atmosphere, 39 mg of 2,4,6-tricyano-1,3,5-mesitylene, 86 mg of 4,4"-diformyl-p-terphenyl, 102 mg of anhydrous piperidine Pyridine, 5mL of anhydrous N,N-dimethylformamide and 5mL of o-dichlorobenzene were added to a 15mL thick-walled pressure-resistant bottle. Seal the thick-walled pressure-resistant bottle with a Teflon screw plug and transfer it to a constant temperature oil In a bath, heat to 120 ° C for 72 hours. After the reaction, the reaction bottle is naturally cooled to room temperature, and the filter residue is collected by vacuum filtration, rinsed with tetrahydrofuran, acetone, methanol and dichloromethane respectively, and the product is collected and stored at 60 °C and vacuum dried for 12 hours to obtain an orange solid. The product was named COF-p-3Ph.

[0046] Add 1.0mmol 4-nitrophenylboronic acid, 5mg COF-p-3Ph, 3.0mmol triethylamine, 5.0mL acetonitrile and a magnetic stir bar into a 10mL glass tube. Submerge the reaction...

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Abstract

The invention discloses a carbon-carbon double bond bridging full-carbon two-dimensional conjugated organic framework material and a preparation method thereof, and relates to the technical field of conjugated organic framework materials (abbreviated as COF), including organic framework materials and a preparation method thereof; The organic framework material has a conjugated all-carbon skeleton structure, including three kinds of COFs, named respectively: COF-p-3Ph, COF-p-2Ph and COF-m-3Ph. Compared with the prior art, the technical solution disclosed in the present invention uses 2,4,6-tricyano-1,3,5-mesitylene as the core monomer for the first time in the preparation process to synthesize carbon A two-dimensional COF bridged by carbon double bonds. The COF has high crystallinity, high specific surface area, uniform pore structure, and semiconductor properties. Due to the characteristics of visible light absorption, semiconductor activity, and porous structure, it can efficiently catalyze under visible light. Oxidation of arylboronic acid substrates to phenolic species.

Description

technical field [0001] The invention belongs to the technical field of conjugated organic framework materials, and relates to a carbon-carbon double bond bridging two-dimensional conjugated organic framework material and a preparation method thereof, in particular to 2,4,6-tricyano-1 , 3,5-Mesitylene as the core monomer and three aryl aldehydes with multiple aldehyde groups were condensed by Brainwenger to prepare a two-dimensional conjugated organic framework material with a full carbon skeleton bridged by carbon-carbon double bonds. Background technique [0002] Conjugated organic framework (covalent organic framework, COF) materials are a kind of porous materials with long-range ordered structure and regular channel structure, which are connected by small organic molecules through covalent bonds in two-dimensional or three-dimensional space. Material. Since the first two-dimensional COF based on boronic acid ester bonds was reported in 2005 (Science, 2005, 310, 1166-1170...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G83/00B01J31/06B01J35/10C07C37/58C07C39/04C07C39/12C07C51/367C07C65/03C07C201/12C07C205/22C07C253/30C07C255/53C07C41/26C07C43/23C07D209/86
CPCC08G83/008B01J31/063C07C37/58C07C51/367C07C201/12C07C253/30C07C41/26C07D209/86B01J35/617B01J35/39B01J35/643B01J35/647C07C39/04C07C39/12C07C65/03C07C205/22C07C255/53C07C43/23Y02P20/52
Inventor 张帆毕帅魏士策张文贝张凡吴东清
Owner SHANGHAI JIAOTONG UNIV
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