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Synthesis process of 1,7-disubstituent-3,4:9,10-perylene bisimide

A technology of perylenebisimide and dibromoperylenediimide, which is applied in the field of organic chemical industry and fine chemical industry, can solve the problems of low substitution reaction yield, difficulty in increasing yield, and many by-products, and shorten the reaction time. time, increased productivity, and low cost effects

Inactive Publication Date: 2005-12-14
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the modification of the 1 and 7 positions of perylene diimide is very mature, mainly through the bromination of the 1 and 7 positions, and the most commonly used bromination is the direct bromination of perylene tetracarboxylic dianhydride sulfuric acid method. The main disadvantages are serious pollution, many by-products and low yield of further substitution reaction
In the phenol substitution reaction, cesium carbonate is mostly used as the base, and the cost is high, and it is difficult to increase the yield by using an aprotic solvent or an unsuitable protic solvent

Method used

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  • Synthesis process of 1,7-disubstituent-3,4:9,10-perylene bisimide
  • Synthesis process of 1,7-disubstituent-3,4:9,10-perylene bisimide
  • Synthesis process of 1,7-disubstituent-3,4:9,10-perylene bisimide

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Add 10 grams of perylenetetracarboxylic dianhydride and 300 milliliters of cyclohexylamine into a 500 milliliter single-necked round-bottomed flask, reflux at 135° C. for 30 hours, and track the progress of the reaction with a thin-layer silica gel plate. Excess cyclohexylamine was distilled off and recovered to generate perylene diimide with a yield of 100%. Perylene diimide and liquid bromine were refluxed for 40 hours at 40°C under the protection of argon in the solvent dichloromethane, and the concentration of bromine was controlled to be 20 g / 100 ml of dichloromethane, and the amount of dichloromethane added was 100 Milliliters per gram of perylene diimide, after the reaction is complete, the mixed solution of dichloromethane and liquid bromine is distilled off at normal pressure and recovered to generate dibromoperylene diimide with a yield of 95%. Add 1.2 grams of dibromoperylene diimide, 0.54 grams of p-tert-butylphenol, 0.48 grams of potassium carbonate and 20 ...

Embodiment 2

[0021] Add 10 grams of perylenetetracarboxylic dianhydride and 400 milliliters of n-butylamine into a 500 milliliter single-necked round bottom flask, reflux at 80°C for 60 hours, and track the progress of the reaction with a thin-layer chromatography silica gel plate. Excess n-butylamine was distilled off and recovered to generate perylene diimide with a yield of 100%. Perylene diimide and liquid bromine were refluxed for 60 hours at 40°C under the protection of argon in the solvent dichloromethane, and the concentration of bromine was controlled to be 10 g / 100 ml of dichloromethane, and the amount of dichloromethane added was 30 Milliliters per gram of perylene diimide, after the reaction is complete, the mixed solution of dichloromethane and liquid bromine is evaporated under normal pressure and recovered to generate dibromoperylene diimide with a yield of 85%. Add 1.2 grams of dibromoperylene diimide, 0.32 grams of phenol, 0.45 grams of sodium carbonate, and 20 milliliters...

Embodiment 3

[0023] Add 10 grams of perylenetetracarboxylic dianhydride and 350 milliliters of n-pentylamine into a 500 milliliter single-necked round-bottomed flask, and reflux at 105° C. for 50 hours. The progress of the reaction was followed by a thin-layer chromatography silica gel plate. Excessive n-pentylamine was distilled off and recovered to generate perylene diimide with a yield of 100%. Perylene diimide and liquid bromine were refluxed for 50 hours at 40°C under the protection of argon in the solvent dichloromethane, and the concentration of bromine was controlled to be 10 g / 100 ml of dichloromethane, and the amount of dichloromethane added was 100 Milliliters per gram of perylene diimide, after the reaction is complete, the mixed solution of dichloromethane and liquid bromine is distilled off at normal pressure and recovered to generate dibromoperylene diimide with a yield of 90%. Add 1.2 g of dibromoperylene diimide and 20 ml of pyrrolidine into a 50 ml single-necked round bot...

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Abstract

The present invention provides the synthesis process of 1, 7-disubstituent-3, 4: 9, 10-perylene bisimide. The synthesis process includes the following steps: A. refluxing perylene tetrabasic dihydride with first-order amine as solvent for 20-60 hr to produce perylene bisimide; B. refluxing perylene bisimide and liquid bromine in dichloromethane solvent for 10-60 hr to produce dibromoperylene bisimide; and C. reacting dibromoperylene bisimide and phenol inside N-methyl pyrrolidone in the presence of carbonate at 90-140 deg.c for 10-60 hr to produce 1, 7-diphenol-3, 4: 9, 10-perylene bisimide; or reacting dibromoperylene bisimide in second-order amine as solvent at 40-70 deg.c for 10-30 hr to produce 1, 7-diimido-3, 4: 9, 10-perylene bisimide.

Description

technical field [0001] The invention relates to the technical fields of organic chemical industry and fine chemical industry, in particular to a synthesis method of 1,7-bis(phenol / imine)-3,4:9,10-perylene bisimide. Background technique [0002] Perylene tetracarboxylic acid diimide (referred to as perylene diimide) as a colorant has received extensive attention in basic theory and industrial dye research. Perylene diimides were originally used industrially as red dyes. Because perylene diimide derivatives have insolubility, light, air, thermal stability, chemical inertness and high coloring power from red to purple, they were used as high-grade industrial dyes after 1950. Recently, perylene diimide has been applied in the field of electronic materials, among which perylene diimide is currently the best n-type semiconductor, and it is most promising to be used in field effect transistors. In addition, due to the unique light, redox and stability, the application of perylene...

Claims

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Application Information

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IPC IPC(8): C07D471/06
Inventor 石志强韩慈祥马永山于莹孙冰邢成芬
Owner SHANDONG NORMAL UNIV
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