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Asymmetric perylene bisimide compounds with star structures and preparing method thereof

A technology of star structure and perylene imide, which is applied in the direction of organic chemistry, etc., to achieve the effects of enhanced solvency, novel structure, and easy charge transfer

Inactive Publication Date: 2014-08-13
HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The molecular structure of the asymmetric peryleneimide prepared from the above reaction materials is that the central nitrogen atom of triphenylamine is the core, and the perylene nucleus plane in the asymmetric peryleneimide monoacid anhydride is the arm. This molecule has a high The regular propeller space configuration has not been reported in the literature so far

Method used

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  • Asymmetric perylene bisimide compounds with star structures and preparing method thereof
  • Asymmetric perylene bisimide compounds with star structures and preparing method thereof
  • Asymmetric perylene bisimide compounds with star structures and preparing method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Preparation of unsymmetrical peryleneimide monoanhydride:

[0032] Add 7.84g (20mM) of 3,4,9,10-perylenetetracarboxylic anhydride into 100ml of 5% potassium hydroxide solution, heat the solution to hydrolyze the ring-opening of the anhydride, and when the pH value of the solution is stabilized between 9.5 and 11.5, add to the system Start to add 20wt% dilute hydrochloric acid aqueous solution dropwise until all the products in the solution just precipitate out. Stop the reaction and cool to room temperature, filter with a funnel and wash with deionized water until the filtrate becomes neutral, then dry to obtain an intermediate product, the color of which is purple.

[0033] Add 4.9ml (3.875g, 30mM) of 2-ethylhexylamine and 4.485g (10mM) of the product from the previous step to a mixed solution of 50ml of isopropanol and water at a volume ratio of 7:3, and react at a low temperature of 0°C for 4 hours , and then heated up to 90°C to react for 2 hours, acidified the sys...

Embodiment 2

[0036] The preparation of the asymmetric perylene imide compound of star structure:

[0037]4,4', 4"-triaminotriphenylamine (290.25mg, 1mmol), asymmetric peryleneimide monoacid anhydride (2.014g, 4mmol) and imidazole (10g, 146mmol) were added to the three-necked flask at one time, and Under the protection of nitrogen, heat to 100°C to melt imidazole into a liquid state. After stirring and reacting at this temperature for 1 hour, react at 130°C for 2 hours and then raise the temperature to 160°C for 3 hours. After the reaction is completed, the system is cooled to room temperature. Pour the product into a mixed solution of methanol and 2mol / L dilute hydrochloric acid aqueous solution to precipitate out, then extract the organic phase with chloroform several times and rotary evaporate to obtain the product, use methanol / chloroform (1:40) as the eluent to separate through the column Dried to obtain the target product with a star structure. The mass of the obtained product was 1.0...

Embodiment 3

[0040] The preparation of the asymmetric perylene imide compound of star structure:

[0041] Add 4,4',4"-triaminotriphenylamine (290.25mg, 1mmol) and asymmetric peryleneimide monoacid anhydride (2.52g, 5mmol) into 20ml m-cresol solvent, heat to 90°C under nitrogen protection ℃, stirred and reacted at this temperature for 2 hours, then added 2ml of isoquinoline, raised the temperature to 160°C for 4 hours, and then raised the temperature to 200°C for 6 hours. After the reaction, the system was cooled to room temperature, and the product was poured into methanol and 2mol / L dilute hydrochloric acid aqueous solution to precipitate, and then extract the organic phase with chloroform for many times and then rotary evaporate to obtain the product, use methanol / chloroform (1:40) as the eluent to separate through the column and dry to obtain a star-shaped structure Target product. The mass of the product obtained was 0.8 g.

[0042] Productive rate 45.8%; Infrared (KBr tablet): 2954-2...

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Abstract

The invention relates to asymmetric perylene bisimide compounds with star structures and a preparing method thereof, and belongs to the field of organic synthesis. The objective of the invention is to design and prepare the asymmetric perylene bisimide compounds with the star structures. The general structure formula of the compounds is shown as the formula (I). 4,4',4''-triamino triphenylamine and asymmetric perylene bisimide monoanhydride with different alkyl chains are adopted as reaction raw materials. The compounds with the star structures are obtained by adding a certain amount of a catalyst and reaction solvent, and reacting at 90-200 DEG C for 6-18 h according to a certain warming gradient. The compounds with the star structures are good in dissolving capacity, maintain the perylene ring plane structure, and are prone to supramolecular self-assembly in solutions. Formation of the donor-acceptor structure between the triphenylamine and the perylene core facilitates intramolecular charge transfer, broadens the molecular spectral absorption range and shortens the band gap of materials. The compounds with the star structures are widely applied in the fields of supramolecular self-assembly and organic optoelectronic materials.

Description

[0001] Technical field: the present invention belongs to the field of organic synthesis, and specifically relates to an asymmetric peryleneimide compound with a star-shaped space structure and a preparation method thereof. Background technique [0002] Perylene imides are a class of compounds with special fused ring structures in their molecular structures, and have a variety of derivatized structures. As a class of cheap and easy-to-obtain organic functional dyes, this type of material has gained great attention in the fields of organic solar cells, electroluminescence, and supramolecular self-assembly in recent years. This is because perylene imide compounds have good photothermal and chemical stability, and have the characteristics of high fluorescence quantum yield; on the other hand, because of their large planar structure and π-π conjugated electron system, this So that it has a high electron affinity and a strong ability to get electrons and the resulting high electron ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10
CPCC07D519/00
Inventor 齐胜利李丰石蕾田国峰武德珍
Owner HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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