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A kind of chiral tetraphenylethylene and its synthetic method

A tetraphenylethylene and synthetic method technology, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve problems such as difficult to obtain CPL materials, achieve excellent aggregation-induced luminescence performance, convenient synthesis, and simple structure

Active Publication Date: 2021-01-12
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since the benzene ring of tetraphenylethylene can rotate, it is difficult to fix its rotation direction by using chiral induction methods, so it is difficult to obtain CPL materials with a single conformation

Method used

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  • A kind of chiral tetraphenylethylene and its synthetic method
  • A kind of chiral tetraphenylethylene and its synthetic method
  • A kind of chiral tetraphenylethylene and its synthetic method

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preparation example Construction

[0044] The preparation method of the α,α'-dimethoxytetraphenylethylene is obtained by performing Suzuki reaction on dibromostilbene and α-methoxyphenylboronic acid. The process of the Suzuki reaction is: under the protection of an inert gas, dissolve dibromostilbene, α-methoxyphenylboronic acid, tetrakis(triphenylphosphine)palladium, and potassium carbonate in a mixed solvent and raise the temperature to 90-95°C react. Suzuki reaction time is 16 ~ 20h. The mixed solvent is a mixture of toluene, water and ethanol, wherein, toluene is used as an organic phase solvent, water is used as an inorganic phase solvent, and ethanol is used as a phase transfer catalyst. The volume ratio of water to ethanol is 1:1, and the volume ratio of toluene, water and ethanol It is 10:1:1. The molar ratio of dibromostilbene, α-methoxyphenylboronic acid, tetrakis(triphenylphosphine)palladium, and potassium carbonate is 1:5:0.1:5. The ratio of dibromostilbene to toluene is 1 mmol: 15 mL.

[0045]T...

Embodiment 1

[0050] Embodiment 1α, the synthesis of α '-dimethoxytetraphenylethylene

[0051] 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 90°C, and continue the reaction for 18h; after the reaction, extract with dichloromethane (3×50mL) , combine the organic phases; use anhydrous magnesium sulfate to dry and remove the solvent; use n-hexane / dichloromethane (90 / 10) as the mobile phase for column chromatography to obtain a white solid, which is α,α′-dimethyl Oxytetraphenylethylene (referred to as compound 1), yield 73%.

Embodiment 2

[0052] Example 2α, the synthesis of α'-dihydroxytetraphenylethylene

[0053] Compound 1 (0.392g, 1.0mmol) was placed in a 50mL reactor; under nitrogen protection, 10mL of dry dichloromethane was added, stirred until dissolved; cooled to -65°C, stirred for 15min; added 4.0mL of boron tribromide Dichloromethane solution (1.0mol / L), take out the reactor, put it at room temperature; stir at room temperature for 12h; take 100mL deionized water and place it in a 250mL round bottom bottle; bubble nitrogen for 10min; pour the liquid in the reactor put into a round-bottom flask under nitrogen protection, and stir for 1 h; extract with dichloromethane (3×50 mL), combine the organic phases; dry over anhydrous magnesium sulfate and remove the solvent to obtain a white solid, which is α,α′-di Hydroxytetraphenylethylene (referred to as compound 2), yield 90%.

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Abstract

The invention discloses a chiral tetraphenylethylene and its synthesis method. Its chemical structural formula is or its synthesis method is as follows: first, α,α′-dimethyl is obtained by using benzophenone as raw material by using Corey-Fuchs reaction and Suzuki reaction Oxytetraphenylethylene. After hydrolysis, react with binaphthol with two alkyl chains at the end of the hydroxyl group, use the stretching of the two alkyl chains of binaphthol to fix the two conformations of tetraphenylethylene, and obtain a stable presence in aqueous solution A single conformation of tetraphenylethylene, that is, chiral tetraphenylethylene in the true sense.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, and relates to a chiral tetraphenylethylene and a synthesis method. Background technique [0002] Circularly polarized luminescence (CPL) is an optical phenomenon unique to certain chiral luminescent substances, and it plays an important role in characterizing the excited state information of chiral molecules. The optical characteristics of circularly polarized luminescence make it have potential application prospects in information storage, sensing and display, which makes the research of CPL materials more and more attention in recent years. Tetraphenylethylene has a simple molecular structure, is convenient for synthesis and modification, and has excellent aggregation-induced luminescent properties. However, since the benzene ring of tetraphenylethylene can rotate, it is difficult to fix its rotation direction by chiral induction, so it is difficult to obtain CPL material...

Claims

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Application Information

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IPC IPC(8): C07D323/00C09K11/06
CPCC07D323/00C09K11/06C09K2211/1007C09K2211/1088
Inventor 柏铭卢相城李家乐张梦醒戚明颖
Owner SHANDONG UNIV
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