Synthetic method of 1-nitro-3,4:9,10-perylene tetracarboxylate and 1,6(7)-dinitro-3,4:9,10-perylene tetracarboxylate

A technology of perylene tetracarboxylate and a synthesis method, which is applied in the field of organic synthesis, can solve the problems of low yield, non-single product, difficult to control and the like, and achieves the effects of high yield, single product and mild reaction conditions

Inactive Publication Date: 2016-07-06
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the derivatization of 3,4:9,10-perylene tetracarboxylate is started by bromination reaction, using chloroform as solvent, reacting with bromine to obtain 1-bromo-3,4:9,10 -perylene tetracarboxylate and 1,6(7)-dibromo-3,4:9,10-perylene tetracarboxylate, but these several products are often generated simultaneously, the products are not single, and the yield is low ,hard to control

Method used

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  • Synthetic method of 1-nitro-3,4:9,10-perylene tetracarboxylate and 1,6(7)-dinitro-3,4:9,10-perylene tetracarboxylate
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  • Synthetic method of 1-nitro-3,4:9,10-perylene tetracarboxylate and 1,6(7)-dinitro-3,4:9,10-perylene tetracarboxylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] In a 50mL round bottom flask, add 3,4:9,10-n-butyl perylenetetracarboxylate (200mg, 0.3mmol) and 20mL of dichloromethane, ultrasonically shake to dissolve, and slowly drop into the reaction system under stirring at room temperature Add 0.5mL fuming nitric acid, follow the reaction by TLC, and react for about 1 hour. When 1,6(7)-dinitro-3,4:9,10-perylenetetracarboxylate is identified by TLC, the reaction is stopped, and the The reaction solution was transferred to a separatory funnel, washed repeatedly until the water layer became neutral, the organic layer was separated, dried over anhydrous sodium sulfate, the solvent was removed by rotary evaporation, and vacuum-dried at 70°C for 5 hours. The crude product was separated and purified by silica gel column chromatography (dichloromethane:petroleum ether=2:1) ​​to obtain 190 mg of n-butyl 1-nitro-3,4:9,10-perylenetetracarboxylate with a purity of 99%. The yield was 91%. figure 1 For the mass spectrogram of the compound p...

Embodiment 2

[0033] In a 50mL round bottom flask, add 3,4:9,10-n-butyl perylenetetracarboxylate (200mg, 0.3mmol) and 20mL of chloroform, ultrasonically shake to dissolve, and slowly drop into the reaction system under stirring at room temperature Add 0.5mL fuming nitric acid, follow the reaction by TLC, and react for about 1 hour. When 1,6(7)-dinitro-3,4:9,10-perylenetetracarboxylate is identified by TLC, the reaction is stopped, and the The reaction solution was transferred to a separatory funnel, washed repeatedly until the water layer became neutral, the organic layer was separated, dried over anhydrous sodium sulfate, the solvent was removed by rotary evaporation, and vacuum-dried at 70°C for 5 hours. The crude product was separated and purified by silica gel column chromatography (dichloromethane:petroleum ether=2:1) ​​to obtain 192 mg of n-butyl 1-nitro-3,4:9,10-perylenetetracarboxylate with a purity of 99%. The yield was 92%.

Embodiment 3

[0035] In a 50mL round bottom flask, add 3,4:9,10-n-butyl perylenetetracarboxylate (200mg, 0.3mmol) and 20mL of dichloromethane, ultrasonically shake to dissolve, and slowly drop into the reaction system under stirring at room temperature Add 1.5mL fuming nitric acid, follow the reaction by TLC, and react for about 5 hours. When 1-nitro-3,4:9,10-perylenetetracarboxylate cannot be identified by TLC, stop the reaction, and transfer the reaction solution to the liquid funnel, washed repeatedly until the water layer was neutral, separated the organic layer, dried over anhydrous sodium sulfate, rotary evaporated to remove the solvent, and dried under vacuum at 70°C for 5h. The crude product was separated and purified by silica gel column chromatography (dichloromethane:petroleum ether=2:1) ​​to obtain 200 mg of n-butyl 1,6(7)-dinitro-3,4:9,10-perylenetetracarboxylate , with a purity of 99% and a yield of 90%. image 3 For the mass spectrogram of the compound prepared in this embod...

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Abstract

The invention discloses a method for synthesizing 1-nitro-3,4:9,10-perylene tetracarboxylate and 1,6(7)-dinitro-3,4:9,10-perylene tetracarboxylate method, using 3,4:9,10-perylene tetracarboxylate as raw material, fuming nitric acid as nitrating reagent, by controlling the reaction time, TLC tracking reaction, can obtain 1-nitro-3,4:9, 10-perylene tetracarboxylate and 1,6(7)-dinitro-3,4:9,10-perylene tetracarboxylate. The method of the invention has a single product and a high yield, which solves the problem that the bromination reaction does not have a single product and a low yield; the reaction condition is mild, and the reaction steps are simple and easy to control; the product obtained by the reaction has high purity.

Description

technical field [0001] The present invention relates to the synthesis of 1-nitro-3,4:9,10-perylene tetracarboxylate and 1,6(7)-dinitro-3,4:9,10-perylene tetracarboxylate The method belongs to the technical field of organic synthesis. Background technique [0002] Perylene compound is a very important organic optoelectronic material. It has a large conjugated planar structure and high fluorescence quantum yield. It is considered as a closed chromophore. In addition, it also has excellent chemical, optical and optical properties. thermal stability. Based on the above characteristics, the research on the synthesis of perylene compounds has received more and more attention. [0003] Most of the synthesis of perylene-based compounds is based on perylene anhydride as the starting material. Usually, the perylene anhydride is dissolved in concentrated sulfuric acid for bromination, or the end of the perylene anhydride is imidized first to obtain perylene tetracarboxylic acid diacy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C201/08C07C205/57
Inventor 石志强孙兆振王永霞
Owner SHANDONG NORMAL UNIV
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