Synthesizing method for tetracarboxylic acid N,N,N',N'-tetra (4-carboxyl vinyl phenyl)-1,4-phenylenediamine

A technology of vinyl phenyl and tetracarboxylic acid, applied in the field of synthesis of tetracarboxylic acid N,N,N',N'-tetra-1,4-phenylenediamine

Inactive Publication Date: 2017-11-24
ZUNYI MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • Synthesizing method for tetracarboxylic acid N,N,N',N'-tetra (4-carboxyl vinyl phenyl)-1,4-phenylenediamine
  • Synthesizing method for tetracarboxylic acid N,N,N',N'-tetra (4-carboxyl vinyl phenyl)-1,4-phenylenediamine
  • Synthesizing method for tetracarboxylic acid N,N,N',N'-tetra (4-carboxyl vinyl phenyl)-1,4-phenylenediamine

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preparation example Construction

[0022] of the present invention N , N , N ', N The synthetic method of '-tetra(4-carboxyvinylphenyl)-1,4-phenylenediamine, the synthetic steps are:

[0023] Using 1,4-dibromobenzene and diphenylamine as raw materials, it is produced by Buchwald-Hartwig aryl amination reaction N,N,N',N' -Tetraphenyl-1,4-phenylenediamine (A), produced by the bromination reaction of A and NBS N,N,N',N' -Tetrakis(4-bromophenyl)-1,4-phenylenediamine (B), the synthetic route is as follows figure 2 shown. B reacts with methyl acrylate to generate by Heck reaction N,N,N',N' -Tetrakis(4-methoxycarbonylvinylphenyl)-1,4-phenylenediamine (C), C is finally hydrolyzed to obtain the target compound N,N,N',N' -Tetrakis(4-carboxyvinylphenyl)-1,4-phenylenediamine (D), the synthetic route is as follows image 3 shown.

specific Embodiment

[0025] (i) if figure 2 Shown: weigh 1,4-dibromobenzene (2.9 g, 12.3 mmol), diphenylamine (5.0 g, 29.6 mmol), bis(dibenzylidene ketone) palladium (0.04 g, 0.07 mmol), tert-butanol Sodium (2.9 g, 30.2 mmol) was added to a 250 mL three-neck flask, 50 mL of toluene was added, and 3.5 mL of tris-(2-tolyl)phosphine was added quickly after argon gas flowed for 15 min, and the reaction was carried out in an oil bath at 90°C under the protection of argon After 12 h, the toluene was distilled off at the end of the reaction, diluted with 30 mL of water, extracted with dichloromethane (30 mL×3), the organic layer was collected, and anhydrous Na 2 SO 3 Dry, filter, and distill off the solvent to obtain the reaction crude product, which is purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 20:1) after drying to obtain white powder A (3.04 g, 7.4 mmol ). The rate is 60%. Melting point: 197~198°C.

[0026] Compound A NMR 1 H NMR, 13 C NMR and high-res...

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Abstract

The invention relates to a synthesizing method for tetracarboxylic acid N,N,N',N'-tetra (4-carboxyl vinyl phenyl)-1,4-phenylenediamine. The method comprises the following steps: generating N,N,N',N'-tetraphenyl-1,4-phenylenediamine (A) through the aryl amination reaction of 1,4-dibromo-benzene and diphenylamine; reacting A with NBS, thereby generating N,N,N',N'-tetra (4-bromophenyl)-1,4-phenylenediamine (B); adding a catalyst and reacting the compound B with methyl acrylate under the condition of inert gas protection, thereby generating N,N,N',N'-(4-methoxycarbonyl vinyl phenyl)-1,4-phenylenediamine (C); generating a target compound D, namely N,N,N',N'-tetra (4-carboxyl vinyl phenyl)-1,4-phenylenediamine, through the hydrolysis reaction of the compound C. According to the synthesizing method, a polyphenyl aromatic tetracarboxylic acid compound which has not been reported in literature is synthesized. The synthesizing method has the advantages of simple synthesizing method, low compounding cost, high yield and high product purity. The target compound D is as shown in the specification.

Description

technical field [0001] The present invention relates to tetracarboxylic acids N , N , N ', N Synthetic method of '-tetra(4-carboxyvinylphenyl)-1,4-phenylenediamine. Background technique [0002] Extended rigid aromatic carboxylic acid ligands are widely used in the construction of MOFs materials. Such materials usually have good pore structure and large specific surface area, which make these materials useful in energy gas storage and separation, catalysis, chemical sensing and There are potential applications in different fields such as sustained release of drugs. For example, MOFs can adsorb carbon dioxide at a specific temperature and pressure, and the desorption temperature only needs to be 50 °C higher than the adsorption temperature. The results of spectral analysis, diffraction analysis and theoretical calculation show that the CO 2 The intense absorption of is an unprecedented synergistic process. If you flatten MOFs the size of a sugar cube, it could be as l...

Claims

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Application Information

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IPC IPC(8): C07C227/18C07C229/44
CPCC07C227/18C07C209/10C07C209/74C07C227/10C07C229/44C07C211/56C07C211/54
Inventor 史大斌孟超
Owner ZUNYI MEDICAL UNIVERSITY
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