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Chiral poly (3,4-ethylenedioxythiophene) derivative monomer, polymer and preparation method thereof

A technology for ethylenedioxythiophene and derivatives is applied in the field of chiral poly(3,4-ethylenedioxythiophene) derivative monomers and polymers and their preparation, and achieves low cost, wide application prospects and high performance. excellent effect

Inactive Publication Date: 2012-03-28
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, there has been no report on the functionalization of monomer 3,4-ethylenedioxythiophene (EDOT) into chiral molecules with chiral amino acids and electropolymerization

Method used

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  • Chiral poly (3,4-ethylenedioxythiophene) derivative monomer, polymer and preparation method thereof
  • Chiral poly (3,4-ethylenedioxythiophene) derivative monomer, polymer and preparation method thereof
  • Chiral poly (3,4-ethylenedioxythiophene) derivative monomer, polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: Synthesis of monomer compound EDOT-Boc-Ala

[0031] The synthesis scheme of monomeric EDOT-Boc-Ala is as follows:

[0032] .

[0033] Concrete synthetic steps are as follows:

[0034] 1, the synthesis of 3,4-dimethoxythiophene

[0035] in N 2 Under protection, 3,4-dibromothiophene (50.01 g, 206.67 mmol), copper oxide (16.50 g, 207.42 mmol) and potassium iodide (1.37 g, 8.25 mmol) were added to a 1000-mL three-necked flask, and the mass fraction 28% sodium methoxide solution (208.0 g, 1.08 mol) and 200 mL methanol. Reflux and stir for 96 h, TLC monitors the completion of the reaction, the reaction solution is cooled to room temperature and filtered, and the filter cake is washed with methanol. Pour the filtrate into 500 mL of water. Extract with dichloromethane, combine the organic phases and dry over anhydrous magnesium sulfate, remove the solvent by rotary evaporation under reduced pressure, and separate by silica gel column chromatography (petrol...

Embodiment 2

[0056] Example 2: Electrochemical Polymerization of PEDOT-Boc-Ala

[0057] Use refined dichloromethane as the electrolyte, the concentration is 0.02 mol L -1 EDOT-Boc-Ala is the reactive monomer, 0.1 mol L -1 Tetrabutylammonium boron tetrafluoride as the electrolyte. Stir evenly, and keep the solution in an argon atmosphere after protecting it with argon. at 20 o C. 25 o C. 30 o C and 35 o C. At four different temperatures, in a three-electrode system in which the platinum sheet is the working electrode and the counter electrode, and the platinum wire reference electrode, the constant potential polymerization is carried out under stirring. A working potential of 1.30 V was applied during polymerization. A blue-black solid can be obtained. The products prepared at four different temperatures are basically the same. The product is soaked in concentrated ammonia water for 3 days and dried. The specific rotation of the dedoped state is [α] 20.0 =-191.08°. Test the infra...

Embodiment 3

[0058] Example 3: Electrochemical Polymerization of PEDOT-Boc-Ala

[0059] The chiral PEDOT derivative was prepared according to the steps of Example 2, but the concentration of the monomer EDOT-Boc-Ala was 0.04 mol / L, and the same result was obtained.

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Abstract

The invention discloses a chiral poly (3,4-ethylenedioxythiophene) derivative monomer, a polymer and a preparation method thereof. The method comprises the following steps of: obtaining the chiral monomer EDOT-Boc-Ala by using 3,4-dibromothiophene as a raw material and adopting six-step reaction, and performing direct deposition to obtain a polymer poly (EDOT-Boc-Ala) film on a platinum electrode by using dichloromethane as an electrolysis solution, using tetrabutyl ammonium tetrafluoroborate as an electrolyte and adopting an electrochemical method. The specific rotation of the prepared monomer is [alpha] 20.0=-30.77 degrees, and the specific rotation of the polymer is [alpha] 20.0=-191.08 degrees; and the monomer can be dissolved into solvents such as acetone, dimethyl sulfoxide and the like, so the monomer can be applied in the field of chromatographic separation of chiral inducers, chiral catalysts, chiral medicament enantiomer and the like.

Description

technical field [0001] The invention belongs to the field of organic conductive polymers, in particular to a chiral poly(3,4-ethylenedioxythiophene) derivative monomer and polymer and a preparation method thereof. Background technique [0002] At the molecular level, chirality is ubiquitous in nature. Many important biological compounds are chiral, such as natural amino acids, simple sugars, etc., and more importantly, they have only one optical enantiomer (mirror image) structure. Helical chirality is ubiquitous in important biopolymers (such as proteins, nucleic acids, and DNA, etc.), which makes animals and plants show unique specificity in metabolic processes. In organisms, the active sites of various enzymes can only bind specific chiral optical isomers in the substrate. Therefore, in practical applications such as chiral drugs and pesticides, the control of chirality is a very important factor. For decades, scientists have devoted a lot of energy in the design and s...

Claims

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Application Information

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IPC IPC(8): C07D495/04C25B3/00
Inventor 段学民卢瑶徐景坤卢宝阳陈帅黄瑶
Owner JIANGXI SCI & TECH NORMAL UNIV
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