Amphiphilic ethylene derivative and preparation method

An ethylene derivative and amphiphilic technology, which is applied in the fields of ether preparation, ester reaction preparation of ether, chemical instruments and methods, etc., can solve problems such as difficulty in dihedral angle, and achieve the effects of simple structure, convenient synthesis, and excellent aggregation-induced luminescence performance.

Inactive Publication Date: 2020-04-21
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the rotation of the tetraphenylethylene benzene ring, it is difficult to control the dihedral angle in its aggregated state

Method used

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  • Amphiphilic ethylene derivative and preparation method
  • Amphiphilic ethylene derivative and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of α,α'-Dimethoxytetraphenylethylene

[0036] Dibromostilbene (2.028g, 6mmol), α-methoxyphenylboronic acid (4.56g, 30mmol), potassium carbonate (4.416g, 30mmol), palladium tetrakistriphenylphosphine (693mg, 0.6mmol) In a 250mL round bottom bottle; under nitrogen protection, add 100mL toluene, 2mL water, 2mL ethanol, stir until dissolved, raise the reaction temperature to 110°C, and continue the reaction for 18h; after the reaction, extract with dichloromethane (3×50mL) , the organic phases were combined; the solvent was removed after drying with anhydrous magnesium sulfate; column chromatography separation was performed using n-hexane / dichloromethane (90 / 10) as the mobile phase to obtain a white solid with a yield of 73%.

Embodiment 2

[0038] Synthesis of α,α'-Dihydroxytetraphenylethylene

[0039] Put α,α'-dimethoxytetraphenylethylene (0.392g, 1.0mmol) in a 50mL reactor; add 10mL of dry dichloromethane under nitrogen protection, stir until dissolved; cool to -65°C, stir 15min; add 4.0mL of boron tribromide in dichloromethane solution (1.0mol / L), take out the reactor, and put it at room temperature; stir at room temperature for 12h; take 100mL of deionized water and place it in a 250mL round bottom bottle; Bubbling for 10 min; pour the liquid in the reactor into a round-bottomed bottle under nitrogen protection, and stir for 1 h; extract with dichloromethane (3×50 mL), combine the organic phases; dry with anhydrous magnesium sulfate and remove the solvent to obtain a white Solid, 90% yield.

Embodiment 3

[0042] Such as figure 1 Synthesis of shown compound 1 (n=1 alkoxy chain substituted tetraphenylethylene)

[0043] Put α,α'-dihydroxytetraphenylethylene (0.364g, 1mmol) and potassium carbonate (1.38g, 10mmol) in a 150mL round bottom bottle; add 50mL of dry acetone under nitrogen protection, stir until dissolved; add 2 -Bromoethyl methyl ether (0.556g, 4mmol); warm up to 60°C, react for 12h; extract with ethyl acetate (3×50mL), combine the organic phases; use anhydrous magnesium sulfate to remove the solvent after drying; use n-hexane / ethyl acetate (80 / 20) was used as the mobile phase for column chromatography to obtain a light yellow viscous liquid with a yield of 80%.

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PUM

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Abstract

The invention discloses an amphiphilic ethylene derivative and a preparation method. The chemical structural formula of the amphiphilic ethylene derivative is shown in the specification, wherein n isa positive integer. The preparation mechanism is as follows: alpha,alpha'-dimethoxytetraphenyl ethylene is used as a raw material to react with halogenated alkoxy chains with different chain lengths,so that polyethylene glycol chains with different chain lengths are introduced into the alpha positions of adjacent benzene rings of the tetraphenyl ethylene, the conformation of the tetraphenyl ethylene during aggregation is controlled by utilizing the hydrophilicity of the polyethylene glycol chains, and the luminescence of the tetraphenyl ethylene dye is further adjusted.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, and specifically relates to an amphiphilic tetraphenylethylene with polyethylene glycol functional group as a hydrophilic group and a preparation method thereof. Background technique [0002] In theory, tetraphenylethylene has a means of controlling luminescence - conformational control. Due to the delocalized conjugated system can reduce π-π * Therefore, the benzene ring in the tetraphenylethylene molecule should adopt a smaller dihedral angle with C=C to form a larger delocalized system. If the dihedral angle between tetraphenylethylene benzene ring and C=C can be controlled, tetraphenylethylene can be further controlled to emit light. However, it is difficult to control the dihedral angle in the aggregated state due to the rotation of the tetraphenylethylene benzene ring. Contents of the invention [0003] In order to solve the deficiencies of the prior art, one of th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/16C07C43/215C09K11/06C09K11/02
CPCC07C41/16C09K11/025C09K11/06C09K2211/1007C07C43/215
Inventor 柏铭张梦醒李家乐虞丽容
Owner SHANDONG UNIV
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