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Alkyl side-chain type phenyl boron fluoride complexes as well as preparation method and application thereof

A chain phenyl boron complex technology, applied in the alkyl side chain phenyl boron fluoride complex and its preparation method and application field, can solve the problem of few piezochromic materials, harsh synthesis conditions, complex synthesis process, etc. problems, to achieve the effect of short reaction cycle, broaden the application market, and simple synthesis process

Active Publication Date: 2018-10-12
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Alkyl side-chain type phenyl boron fluoride complexes as well as preparation method and application thereof
  • Alkyl side-chain type phenyl boron fluoride complexes as well as preparation method and application thereof
  • Alkyl side-chain type phenyl boron fluoride complexes as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

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

Embodiment 2

[0035] (1) Combine 7.5g (22.39 mmol) 2-bromo-1,1,2-tristyrene (II) with 4.03g (24.58 mmol) 4-acetylphenylboronic acid and 0.06g tetrakistriphenylphosphine palladium , 5.96g potassium carbonate, 3.97g tetrabutylammonium bromide were added to a dry reaction vessel filled with nitrogen, 80ml xylene was added, heated to reflux at 100°C for 24 hours, cooled to room temperature, and tetrastyrene was extracted with dichloromethane The crude product of base 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 1.56g (4mmol) of the white solid and 1.11g (12mmol) of methyl propionate into a dry reaction vessel with nitrogen, add 30ml of solvent dichloromethane, 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 slightly dry, petroleum eth...

Embodiment 3

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

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

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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-fluorine complex and a preparation method and application thereof, belonging to the field of organic synthesis. Background technique [0002] Mechanical tribochromic (MFC) materials have excellent properties such as unique molecular aggregation-induced luminescence (AIE), high luminous efficiency, mechanochromism, and solvent discoloration, making them useful in information security, memory devices, sensors, fluorescent switches, etc. Huge application prospects. As a new type of smart material, the chromophore of this type of material will respond to the increase of mechanical forces such as grinding and pressing, and then its color will change. [0003] Since the discovery of the tribochromic properties of materials, scientists have synthesized many molecules with MFC properties and studied their photochemical properties. In 2001, Tang Benzhong et al. reported for the first time the molecular aggreg...

Claims

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Application Information

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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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