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Preparation of poly(2,5-diakoxy-1,4-benzene)

A dialkoxybenzene and dialkoxy technology, which is applied in the field of preparation of poly(2,5-dialkoxy-1,4-benzene), can solve the problems affecting material properties, the effect of polydialkoxy on Problems such as poor regioregularity of benzene, to achieve the effect of shortening the reaction time, improving the preparation technology and product quality, and eliminating the reaction step

Inactive Publication Date: 2005-11-30
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The more important problem is that the regioregularity (regioregularity) of the polydialkoxy group synthesized by the oxidative coupling method to benzene is not good, and the 1,3-position link is generated while forming the 1,4-position link of the benzene ring, which affects the material. performance

Method used

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  • Preparation of poly(2,5-diakoxy-1,4-benzene)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: 0.61 g of p-dibutoxybenzene and 1.00 g of anhydrous ferric chloride were weighed into a mortar and ground at room temperature. After milling for 30 minutes, the reaction was stopped. Wash the product in the mortar with ethanol or methanol, and separate the solid and liquid by centrifugation to remove ferric chloride and unreacted monomers. The separated solid was washed with ethanol or methanol, and then dried in a constant temperature oven (50° C.). After drying, dissolve the product completely with a small amount of chloroform, add methanol or ethanol four to five times the amount of chloroform to precipitate the polymer, centrifuge again to separate the solid from the liquid, and dry it in a constant temperature oven (50°C) to obtain the product Poly(2,5-dialkoxy-1,4-benzene) 0.44 g, yield 72%. The number average molecular weight of the polymer as determined by size exclusion chromatography was 30,000. After 300 M NMR analysis, the hydrogen spectrum res...

Embodiment 2

[0022] Example 2: Weigh 0.61 grams of p-dibutoxybenzene and 2.00 grams of mixed anhydrous rare earth chloride (Baotou industrial product, containing La27%, Ce51%, Nd15%, Pr5% in rare earth) and put it into a mortar medium grind. After grinding for 20 minutes, put it into a constant temperature oven (60° C.) for 0.5 hour. After continuing grinding for 10 minutes, the reaction was stopped. Wash the product in the mortar with water, and separate the solid and liquid by filtration to remove the rare earth. The solid was washed twice with ethanol or methanol, and then dried in a constant temperature oven (50° C.). After drying, wash the product with ethanol, then separate the solid from the liquid by centrifugation, pour off the supernatant, and leave the precipitate. Then the precipitate was dried in an oven to obtain the product poly(2,5-dialkoxy-1,4-benzene). After the product is completely dissolved by adding chloroform, blue fluorescence can be seen under the irradiation o...

Embodiment 3

[0023] Example 3: 0.61 g of p-dibutoxybenzene and 0.81 g of anhydrous copper chloride were weighed and ground in a mortar. After grinding for 10 minutes, put it into a constant temperature oven (50° C.) for 1 hour. After continuing grinding for 10 minutes, the reaction was stopped. Wash the product in the mortar with ethanol or methanol, and separate the solid and liquid by centrifugation to remove copper chloride and unreacted monomers. The solid was washed three times with ethanol or methanol, and then dried in a constant temperature oven (50° C.). After drying, the product poly(2,5-dialkoxy-1,4-benzene) was obtained. It is completely dissolved in chloroform, and blue fluorescence can be seen under the irradiation of ultraviolet light. The product has been analyzed by 300 M NMR and Fourier transform infrared spectrum, which proves that the linking mode of the benzene ring is 1, 4 linking, and the polymer has a good regioregular structure.

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Abstract

The invention discloses a method for preparing poly(2,5-dialkoxy-1,4-benzene) by solid-state oxidative coupling polymerization. The method uses p-dialkoxybenzene with an alkoxy carbon number of 1 to 18 as a monomer, uses metal chloride as a catalyst, and reacts at 5 to 65°C for 10 to 30 minutes under mixing and grinding to obtain a crude product; separation , and purification to obtain poly(2,5-dialkoxy-1,4-benzene). Because the present invention does not use a solvent during the polymerization reaction, the pollution of the environment is reduced; the production cost is reduced; the polymerization reaction time is short, only needing 10-30 minutes, so that the production efficiency is improved; the polymerization yield is improved, which can reach 90%; The polymer has good structural regioregularity, and all the benzene rings are linked in the para position. The fluorescence emission peak of the obtained polymer is about 405 nanometers, which belongs to the blue-violet light emission material. This conjugated polymer can be used in the manufacture of electroluminescent devices, organic thin film transistors and other photoelectric conversion devices.

Description

technical field [0001] The invention relates to a preparation method of poly(2,5-dialkoxy-1,4-benzene) whose main chain is composed of poly-p-phenylene and side chain has alkoxy groups. Background technique [0002] Polyparaphenylene (PPP) and its derivatives are main chain conjugated polymers whose main chain is composed of phenyl links in para positions. It has broad applications in organic semiconductor thin film transistors, organic electroluminescent display devices and information technology. application prospects. In particular, it is used as a polymer film light-emitting layer in organic electroluminescent display devices, and has the advantages of low-voltage DC voltage drive, ultra-thin, and full curing. Synthetic main chain is made up of the conjugated polymer of polyparaphenylene, must introduce halogen atom on the benzene ring, by Ullmann reaction (Ullmann Reaction) or Suzuki reaction [Synthetic Communications, 11 (7), 513-519, 1981. ] Condensation to remove h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F232/06
Inventor 詹才茂白卫斌
Owner WUHAN UNIV
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