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Tetraphenyl ethylene derivative ion complex and preparation method thereof

An ion complex and tetraphenylethylene technology, which is applied in the field of tetraphenylethylene derivative ion complex and preparation, can solve the problems of complex synthesis steps, low yield and the like, and achieves simple preparation method and high yield , the effect of obvious aggregation-induced luminescence effect

Inactive Publication Date: 2017-01-11
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The second object of the present invention is to overcome the disadvantages of complex synthesis steps and low yields in the prior art, and provide a tetraphenylethylene derivative ion complexation through ion self-assembly, simple steps, and high yield. method of preparation

Method used

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  • Tetraphenyl ethylene derivative ion complex and preparation method thereof
  • Tetraphenyl ethylene derivative ion complex and preparation method thereof
  • Tetraphenyl ethylene derivative ion complex and preparation method thereof

Examples

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Effect test

Embodiment 1

[0042] The preparation method of four-(4-hydroxyphenyl)ethylene (III), comprises the steps:

[0043] (1)N 2 Under protection, add 150ml of dry tetrahydrofuran into a 500ml two-neck flask, stir at room temperature for 5min, add zinc powder, slowly add titanium tetrachloride dropwise in ice bath, reflux at 75°C for 2h, cool to room temperature, add 20g of 4,4 '-Dimethoxybenzophenone (I), in N 2 During protection, react at 75°C for 24 hours to obtain mixture 2; the amount of zinc powder added is 33% of the mass of 4,4'-dimethoxybenzophenone (I); the addition of titanium tetrachloride The amount is 48% of the quality of 4,4'-dimethoxybenzophenone (I);

[0044] (2) With the potassium carbonate of mixture 2,20g, the deionized water of 20ml and the dichloromethane of 120ml, after fully mixing, vacuum filter with diatomaceous earth, after the obtained filtrate is rotary evaporated to remove solvent, the residue is used Dichloromethane and methanol were recrystallized to remove unre...

Embodiment 2

[0050] A preparation method of tetraphenylethylene derivative ion complex, comprising the steps of:

[0051] (1) Weigh 0.5g (1.26mmol) of tetra-(4-hydroxybenzene)ethylene (III), 1.16g of methyl 4-bromomethylbenzoate, dissolve with 20ml of acetone, add 0.7g of potassium carbonate and 122mg (0.379 mmol) phase transfer catalyst tetrabutylammonium bromide; heated to reflux for 18h to obtain mixture 1; acetone was removed by rotary evaporation, the residue was dissolved in dichloromethane, extracted three times with saturated aqueous sodium chloride solution, and the organic layer was collected with anhydrous Sodium sulfate is dried, and the dichloromethane solvent is removed by rotary evaporation of the dried organic solution, and the residue is recrystallized with dichloromethane / methanol, and a precipitate is precipitated, filtered and dried to obtain compound (IV), and the molecular weight of compound (IV) is 989.09 , whose structure was characterized by H NMR spectroscopy, see...

Embodiment 3

[0059] A preparation method of tetraphenylethylene derivative ion complex, comprising the steps of:

[0060] (1) Take tetra-(4-hydroxybenzene) ethylene (III) 0.5g (1.26mmol), methyl 4-bromomethylbenzoate 1.45g, dissolve with 20ml acetone, add 0.87g potassium carbonate and 0.2g ( 0.62mmol) phase-transfer catalyst tetrabutylammonium bromide; Heated to reflux for 24h to obtain mixture 1; Rotary evaporation removed acetone, the residue was dissolved in dichloromethane, and extracted three times with saturated aqueous sodium chloride solution, and the organic layer was collected and used without Water sodium sulfate is dried, and the dichloromethane solvent is removed by rotary evaporation of the dried organic solution; The residue is recrystallized with dichloromethane / methanol, and a precipitate is separated out, filtered and dried to obtain compound (IV), and the molecular weight of compound (IV) is 989.09;

[0061] (2) Weigh 0.4g of compound (IV), heat and dissolve in 10mL tet...

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Abstract

The invention discloses a tetraphenyl ethylene derivative ion complex and a preparation method thereof. The tetraphenyl ethylene derivative ion complex is shown in the formula (VII) shown in the specification, wherein R' is one of straight chains with 6-18 carbon atoms, branched chains and naphthenic chains. The tetraphenyl ethylene derivative ion complex has an obvious aggregation-induced emission effect, the yield of solid fluorescence quantum is larger than 40%, and the luminescence property is excellent; the preparation method is simple, the yield is high, purification is easy, and cost is low.

Description

technical field [0001] The invention belongs to the technical field of organic light-emitting materials, and in particular relates to a tetraphenylethylene derivative ion complex with high light-emitting performance and a preparation method. Background technique [0002] Organic light-emitting materials have important application values ​​in light-emitting diodes, fluorescence detection, cell imaging and liquid crystal displays, and have received more and more attention in recent years. Traditional organic light-emitting materials often have high luminescence properties in dilute solutions, but due to the "aggregation-caused quenching" (ACQ) effect, their luminescence properties will drop sharply in concentrated solutions, especially solid states. Not glowing at all. However, in practical applications, organic light-emitting materials mostly appear in solid states such as thin films. Therefore, how to prepare organic materials with excellent light-emitting properties in th...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07C51/41C07C65/24C07C209/68C07C211/63
CPCC07C51/09C07C51/412C07C67/31C07C209/68C09K11/06C07C65/24C07C211/63C07C69/76
Inventor 任相魁荆慧路琳
Owner TIANJIN UNIV
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