A kind of phenylboron fluorine complex and its preparation method and application

A technology of phenyl boron and complexes, which is applied in the field of phenyl boron and fluorine complexes and its preparation, can solve the problems of dangerous environmental pollution, less frictional discoloration materials, complex synthesis process, etc., shorten the reaction time, The effect of short reaction cycle and simple synthesis process

Active Publication Date: 2020-09-15
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Chinese patent application (Application No. 201610355199.9) discloses a method for synthesizing tetrastyryl-containing diketone substances, using tetrastyryl monoketone and ethyl acetate, under the condition of tetrahydrofuran as a solvent, heating to reflux, and reacting 24 Hours, tetrastyryl diketone is obtained, but the material obtained by this method can only be restored to the original color by solvent fumigation. This method is complicated to operate and needs to use a large amount of solvent vapor, which has certain risks and risks. Environmental pollution
At present, there are few tribochromic materials with spontaneous recovery (Chinese patent application 201711034227.8, 201710349483.X), and the synthesis process of these tribochromic materials is complicated, time-consuming, and the synthesis conditions are harsh. Therefore, it is necessary to develop more New recoverable tribochromic material with simple multi-process

Method used

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  • A kind of phenylboron fluorine complex and its preparation method and application
  • A kind of phenylboron fluorine complex and its preparation method and application
  • A kind of phenylboron fluorine complex and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Synthesis of 1-(4-(1,2,2-triphenylethenyl) phenyl) ethanone (tetrastyryl monoketone, III)

[0030] At room temperature, mix 15g (44.7 mmol) 2-bromo-1,1,2-triphenylethylene (II) with 7.5 g (45.7 mmol) 4-acetylphenylboronic acid and 0.1 g (0.087 mmol) tetratriphenyl Phosphine palladium, 11g (79.6 mmol) of potassium carbonate, 7.21g (22.4 mmol) of tetrabutylammonium bromide were added to a dry reaction vessel with nitrogen, 160ml of toluene was added, heated to reflux at 100°C for 24 hours, and cooled to At room temperature, dichloromethane was used to extract the crude product of tetrastyryl monoketone (III). Column chromatography was performed on petroleum ether:dichloromethane=1:1 to obtain 13.40 g of white solid, with a yield of 80%.

[0031] (2) Synthesis of 3-hydroxyl-1-(4-(1,2,-triphenylvinyl)phenyl)but-2-en-1-one (tetrastyryl β-diketone, Ⅳ)

[0032] Add 1.56g (4 mmol) of the above white solid and 100ml of ethyl acetate into a dry reaction vessel with nitrogen ...

Embodiment 2

[0036] Except step (1) and (2), other is with embodiment 1, and the synthetic technique of step (1), (2) is as follows:

[0037] (1) Mix 7.5g (22.39mmol) of 2-bromo-1,1,2-triphenylethylene (II) with 4.03g (24.58mmol) of 4-acetylphenylboronic acid and 0.06g of tetrakistriphenylphosphine palladium , 5.96g of potassium carbonate and 3.97g of tetrabutylammonium bromide were added to a dry reaction vessel with nitrogen, 80ml of xylene was added, heated to reflux at 100°C for 24 hours, cooled to room temperature, and tetraphenylethylene was extracted with dichloromethane The crude product of monoketone (Ⅲ), petroleum ether: dichloromethane = 1:1, was subjected to column chromatography to obtain 6.71 g of white solid with a yield of 80%.

[0038](2) Add 1.56g (4 mmol) of the above-mentioned white solid and 100ml of ethyl acetate into a dry reaction vessel with nitrogen gas, and after the white solid is completely dissolved, add 0.3975g (16.5 mmol) of sodium hydride at 40°C Heated, r...

Embodiment 3

[0040] Except step (2), other is with embodiment 1, and the synthesis technique of step (2) is as follows:

[0041] Add the above-mentioned 1.56g (4 mmol) white solid and 100ml ethyl acetate into a dry reaction vessel with nitrogen, and after the white solid is completely dissolved, add 0.3975g (16.5 mmol) sodium hydride, heat at 50°C, and react After 6 hours, it was cooled to room temperature, and the ethyl acetate in the product was evaporated to dryness, petroleum ether: dichloromethane = 2:1, and purified by column chromatography, and the obtained solid was directly used in the next step of synthesis reaction.

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Abstract

The invention discloses a phenylborofluoride complex capable of recovering color at room temperature and a preparation method of the phenylborofluoride complex and belongs to the field of organic synthesis. The phenylborofluoride complex is prepared from tetraphenylethene beta-diketone and boron trifluoride diethyl etherate by complexing. The preparation method of the phenylborofluoride complex comprises the following steps: (1) preparing tetraphenylethene monoketone from halogen-containing triphenylethylene and acylphenylboronic acid by reaction; (2) synthesizing tetraphenylethene beta-diketone from tetraphenylethene monoketone and ethyl acetate; (3) complexing boron trifluoride diethyl etherate with tetraphenylethene beta-diketone to obtain the phenylborofluoride complex. The phenylborofluoride complex is sensitive to heat, can spontaneously recover to the original color at room temperature after frictional discoloration, and can be repeatedly used. The material has huge applicationprospect in the fields of information security, sensors and the like. Meanwhile, ethyl acetate is used as both a solvent and a reactant, the use of solvents is reduced in the reaction process, and theimpact on the environment is reduced.

Description

technical field [0001] The invention relates to the field of fluorescent material preparation in the field of organic synthesis, in particular to a phenyl boron fluoride complex capable of recovering discoloration at room temperature, a preparation method and application thereof. Background technique [0002] Mechanical tribochromic (MFC) materials are widely used in information security, memory devices, sensors, fluorescent switches, etc. Huge application prospects. As a new type of intelligent material, this type of material will respond to the increase of its chromophore with the increase of mechanical force such as grinding and pressing, and then its color will change. At the same time, this change can be achieved through heating, recrystallization, solvent fumigation, etc. method to return to the original hair color state. [0003] Since the discovery of tribochromic properties of materials, scientists have synthesized many molecules with MFC properties and studied th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06C09K9/02
CPCC07F5/022C09K9/02C09K11/06C09K2211/1007C09K2211/1096
Inventor 张灵赵雄燕王鑫
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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