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A kind of alkyl side chain phenyl boron fluoride complex and its preparation method and application

A technology of chain phenyl boron and complex compound, which is applied to alkyl side chain phenyl boron fluorine complex and its preparation method and application field, can solve the problem of less piezochromic materials, harsh synthesis conditions, complex synthesis process, etc. problem, to achieve the effect of short reaction period, broaden application market and simple synthesis process

Active Publication Date: 2020-09-01
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, few piezochromic materials have been reported (Chinese patent application 201711034227.8, 201710349483.X), and the synthesis process is complex, time-consuming, and synthesis conditions are harsh. Therefore, more piezochromic materials with simple processes need to be developed

Method used

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  • A kind of alkyl side chain phenyl boron fluoride complex and its preparation method and application
  • A kind of alkyl side chain phenyl boron fluoride complex and its preparation method and application
  • A kind of alkyl side chain phenyl boron fluoride complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Mix 7.5g (22.35mmol) of 2-bromo-1,1,2-triphenylethylene (II) with 3.75g (22.85mmol) of 4-acetylphenylboronic acid and 0.05g (0.0435mmol) of four Triphenylphosphine palladium, 5.5g (39.8 mmol) of potassium carbonate, 3.61g (11.2 mmol) of tetrabutylammonium bromide were added to a dry reaction vessel with nitrogen, and 80ml of toluene was added as a solvent, and heated to reflux at 100°C for 24 hours, cooled to room temperature, and extracted the crude product of tetrastyryl monoketone (Ⅲ) with dichloromethane, petroleum ether: dichloromethane=1:1 for column chromatography to obtain 6.68g white solid, yield 80% .

[0032] (2) Add the above-mentioned 1.56g (4 mmol) white solid and 0.37g (4 mmol) methyl propionate into a dry reaction vessel with nitrogen, add solvent 30ml tetrahydrofuran, after the white solid is completely dissolved, add 0.3975g (16.5 mmol) sodium hydride, heated to reflux at 50°C, reacted for 4 hours, cooled to room temperature, and the product was r...

Embodiment 2

[0035] (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%.

[0036] (2) Add the above 1.56g (4 mmol) white solid and 1.11g (12 mmol) methyl propionate into a dry reaction vessel with nitrogen, add 30ml of solvent methylene chloride, and wait until the white solid is completely dissolved , add 0.3975g (16.5 mmol) sodium hydride, heat to reflux at 55°C, react for 3 hours, cool to room temperature, spin evaporate the product to sl...

Embodiment 3

[0039](1) Mix 7.5g (22.39mmol) of 2-bromo-1,1,2-triphenylethylene (II) with 3.75g (22.87mmol) of 4-acetylphenylboronic acid and 0.05g (0.0435mmol) of four Triphenylphosphine palladium, 5.5g (39.8 mmol) of potassium carbonate, 3.61g (11.2 mmol) of tetrabutylammonium bromide were added to a dry reaction vessel with nitrogen, 80ml of toluene was added, and heated to reflux at 100°C for 24 hours , cooled to room temperature, and dichloromethane was used to extract the crude product of tetrastyryl monoketone (Ⅲ), petroleum ether: dichloromethane = 1:1, and column chromatography was performed to obtain 6.68 g of white solid, with a yield of 80%.

[0040] (2) Add 1.56g (4 mmol) of the above white solid and 0.413g (4 mmol) of methyl butyrate into a dry reaction vessel with nitrogen, add 30ml of solvent tetrahydrofuran, and after the white solid is completely dissolved, add 0.3975g (16.5 mmol) sodium hydride, heated to reflux at 60 ° C, reacted for 5 hours, cooled to room temperature, ...

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Abstract

The invention discloses a preparation method of a series of piezochromic phenyl boron fluoride complexes with different alkyl chain lengths. The preparation method of the complexes comprises followingsteps: (1), a halogen-containing triphenylethylene compound and 4-acetylphenylboronic acid are subjected to a reaction, and tetraphenylethylene monoketone is synthesized; (2), tetraphenylethylene monoketone and esters are subjected to a reaction, and tetraphenylethylene beta-diketone compounds with different alkyl chain lengths are obtained; (3), the synthesized tetraphenylethylene beta-diketonecompounds with different alkyl chain lengths are complexed with boron trifluoride diethyl etherate respectively, and a series of boron fluoride complexes with different alkyl chain lengths are obtained. The boron fluoride complexes have excellent molecular aggregation induced fluorescence effect and excellent characteristics of piezochromism, wider wavelength shift range and the like, a new thinking is provided for researching color change mechanism of the piezochromic material by the aid of the synthesis of the material, and the material is expected to be widely applied in the fields of a brain tumor imaging technology, a near-infrared probe technology, photoelectric devices and the like.

Description

technical field [0001] The invention relates to an alkyl side-chain phenyl boron-fluoride complex and a preparation method and application thereof, belonging to the field of organic synthesis. 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 smart material, this type of material will respond to its chromophore with the increase of mechanical force such as grinding and pressing, and then its color will change. [0003] Since the discovery of tribochromic properties of materials, scientists have synthesized many molecules with MFC properties and studied their photochemical properties. In 2001, Tang Benzhong et al. reported the molecular aggregation-induced fluorescence effect for the first time. The research results showed that when the molecules exist in isolation, there is no fluorescence emission, and only when they...

Claims

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Application Information

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