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Water-soluble thiophene monomer and water-soluble polythiophene derivative as well as preparation methods of water-soluble thiophene monomer and water-soluble polythiophene derivative

A water-soluble polythiophene and water-soluble technology, applied in the field of organic polymer optoelectronic materials, can solve problems such as damage and affect the performance of organic light and electrical devices, and achieve the effect of water-solubility

Inactive Publication Date: 2012-01-04
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, almost none of the polythiophene derivatives that have been studied are water-soluble. In the process of manufacturing organic optical and electrical devices, when spin-coating and other methods are used to form films of non-water-soluble polythiophene derivatives, the organic solvents used are It may damage other organic films in organic optical and electrical devices, which will inevitably affect the performance of organic optical and electrical devices

Method used

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  • Water-soluble thiophene monomer and water-soluble polythiophene derivative as well as preparation methods of water-soluble thiophene monomer and water-soluble polythiophene derivative
  • Water-soluble thiophene monomer and water-soluble polythiophene derivative as well as preparation methods of water-soluble thiophene monomer and water-soluble polythiophene derivative
  • Water-soluble thiophene monomer and water-soluble polythiophene derivative as well as preparation methods of water-soluble thiophene monomer and water-soluble polythiophene derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0029] 1), the preparation of water-soluble thiophene monomer:

[0030] In the first step, at N 2 under protection, will N - Methylpyrrolidone and sodium metal were added to a three-necked flask, methanol was slowly added dropwise, and the reaction was stirred at room temperature for 3 h until the sodium metal disappeared. Residual methanol was distilled off under reduced pressure to obtain sodium methylate N - methylpyrrolidone solution;

[0031] In the second step, N 2 Under protection, add the above-mentioned sodium methylate in the three-necked flask N -Methylpyrrolidone solution, cuprous bromide catalyst and 3-bromothiophene, stirred and reacted for 8 h at 100°C, poured the solution into dichloromethane after the reaction, filtered to obtain a reddish-brown solution, in the reddish-brown solution Add saturated sodium chloride solution, extract with dichloromethane, extract the organic phase, dry over anhydrous sodium sulfate, and filter to remove sodium sulfate. Dic...

Embodiment 2

[0043] 1) Preparation of water-soluble thiophene derivative monomer:

[0044] In the first step, at N 2 under protection, will N- Methylpyrrolidone and sodium metal were added to a three-necked flask, methanol was slowly added dropwise, and the reaction was stirred at room temperature for 4 h until the sodium metal disappeared. Residual methanol was distilled off under reduced pressure to obtain sodium methylate N - methylpyrrolidone solution;

[0045] In the second step, N 2 Under protection, add the above-mentioned sodium methylate in the three-necked flask N -Methylpyrrolidone solution, cuprous bromide catalyst and 3-bromothiophene, stirred and reacted for 5 h at 105°C, poured the solution into dichloromethane after the reaction, filtered to obtain a reddish-brown solution, in the reddish-brown solution Add saturated sodium chloride solution, extract with dichloromethane, extract the organic phase, dry over anhydrous sodium sulfate, and filter to remove sodium sulfate....

Embodiment 3

[0057] 1) Preparation of water-soluble thiophene derivative monomer:

[0058] In the first step, at N 2 under protection, will N - Methylpyrrolidone and sodium metal were added to a three-necked flask, methanol was slowly added dropwise, and the reaction was stirred at room temperature for 3.5 h until the sodium metal disappeared. Residual methanol was distilled off under reduced pressure to obtain sodium methylate N - Methylpyrrolidone solution.

[0059] In the second step, N 2 Under protection, add the above-mentioned sodium methylate in the three-necked flask N -Methylpyrrolidone solution, cuprous bromide catalyst and 3-bromothiophene, stirred and reacted for 4 h at 110°C, poured the solution into dichloromethane after the reaction, filtered to obtain a reddish-brown solution, in the reddish-brown solution Add saturated sodium chloride solution, extract with dichloromethane, extract the organic phase, dry over anhydrous sodium sulfate, and filter to remove sodium sulfa...

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Abstract

The invention provides a water-soluble thiophene monomer and a water-soluble polythiophene derivative as well as preparation methods of the water-soluble thiophene monomer and the water-soluble polythiophene derivative. The preparation method of the water-soluble thiophene monomer n-(3-thiophene oxo)-alkyl-triethyl ammonium bromide (n is 2-6) comprises the following steps: reacting methanol with metal sodium in N-methylpyrrolidone, then reacting with 3-bromothiophene, and purifying so as to obtain 3-methoxythiophene; reacting 3-methoxythiophene with n-bromo-1-alkanol (n is 2-6), and purifying so as to obtain 3-(n-bromo-alkoxyl)-thiophene; and reacting 3-(n-bromo-alkoxyl)-thiophene with triethylamine in acetonitrile, and purifying so as to obtain the water-soluble thiophene monomer. According to the invention, the chloroform solution of the water-soluble thiophene monomer is polymerized in the presence of anhydrous ferric trichloride used as a catalyst so as to obtain the water-soluble polythiophene derivative. The water-soluble polythiophene derivative prepared in the invention not only retains good optical and electrical properties of polythiophene but also has water solubility, and is convenient for processing and manufacturing of organic photovoltaic devices.

Description

technical field [0001] The invention relates to the technical field of organic polymer optoelectronic materials, in particular to water-soluble thiophene monomers and water-soluble polythiophene derivatives and their preparation methods. Background technique [0002] Polythiophene and its derivatives are an important class of organic conjugated polymer functional materials. On the one hand, theoretically speaking, polythiophene can be a model for studying the migration of non-degenerate conductive polymers. Due to the high stability of thiophene aromatic heterocycles to oxygen and humidity, its derivatives are more stable than other aromatic heterocycles. Derivatives are easier to synthesize, and the structure of polythiophene derivatives is also diverse; on the other hand, polythiophene doped and dedoped states have good environmental stability. These have aroused more research interest. Therefore, polythiophene and its derivatives are used as conductive materials, light-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/32C08G61/12
Inventor 洪锐彬刘平邓文基
Owner SOUTH CHINA UNIV OF TECH
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