1,7-dicyano-modified perylene imide derivatives and preparation method thereof

A technology of perylene imide and dicyano, which is applied in the field of organic chemical synthesis, can solve the problems of decreased solubility and affected device performance, etc., and achieves the effects of improving solubility, simple preparation method and excellent weather resistance.

Active Publication Date: 2014-07-23
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Due to the π-π stacking between molecules, the solubility of diimide is greatly reduced. When it is used as an organic acceptor photovoltaic material and a donor material, microphase separation will be formed between the materials, which will affect the performance of the device.

Method used

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  • 1,7-dicyano-modified perylene imide derivatives and preparation method thereof
  • 1,7-dicyano-modified perylene imide derivatives and preparation method thereof
  • 1,7-dicyano-modified perylene imide derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] (1) Preparation of 1,7-dibromo-3,4,9,10-perylenetetracarboximide (II):

[0042] Use 1 mmol of perylene tetracarbonyl diimide to correspond to 10 mL of concentrated sulfuric acid (mass concentration 98%), add perylene tetracarbonyl diimide to concentrated sulfuric acid at room temperature, stir and mix for 1 hour at room temperature, iodine catalyst, then raise the temperature to 85°C for reaction for 1 hour, add bromine water dropwise, wherein the millimolar ratio of bromine water to perylenetetracarboximide is 3; stir overnight, and pour the reaction solution after cooling to room temperature Put into ice water, precipitate the solid and filter it with suction, wash the obtained solid with water until the pH value is neutral, and obtain the solid 1,7-dibromo-3,4,9,10-perylenetetracarboximide (II);

[0043] (2) Preparation of 1,7-dibromo-3,4,9,10-perylene tetra-n-butylmethyl perylene (III):

[0044]Add 1,7-dibromo-3,4,9,10-perylenetetracarboximide (II) prep...

Embodiment 2

[0052]

[0053] (1) Preparation of 1,7-dibromo-3,4,9,10-perylenetetracarboximide (II):

[0054] Use 2 mmol of perylene tetracarbonyl diimide to correspond to 20 mL of concentrated sulfuric acid (mass concentration 98%), add perylene tetracarbonyl diimide to concentrated sulfuric acid at room temperature, stir and mix at room temperature for 1.5 hours, add iodine catalyst, then raise the temperature to 85°C for reaction for 1 hour, add bromine water dropwise, wherein the bromine water to perylenetetracarboximide millimole ratio is 3.5; stir overnight, and pour the reaction solution after cooling to room temperature Put into ice water, precipitate the solid and filter it with suction, wash the obtained solid with water until the pH value is neutral, and obtain the solid 1,7-dibromo-3,4,9,10-perylenetetracarboximide (II);

[0055] (2) Preparation of 1,7-dibromo-3,4,9,10-perylene tetra-n-butylmethyl perylene (III):

[0056] Add 1,7-dibromo-3,4,9,10-perylenetetracarboximide (II...

Embodiment 3

[0064]

[0065] Basically the same as Example 1, except that the derivative (VI) of 1,7-dicyano-modified perylene imide is prepared as follows: the 1,7-dicyano-modified peryleneimide obtained in step (4) Imine (V) and aniline are added to the mixed solution of p-xylene and propionic acid (the volume ratio of p-xylene and propionic acid is 4:1), in which, 1,7-dicyano-modified peryleneimide The mmol ratio of aniline to aniline is 7:15; then under the protection of argon, the stirring reaction is carried out at a temperature of 140°C for 1 hour; after the reaction is completed, the obtained product is cooled to room temperature, and ethanol is added to precipitate a solid and filtered to obtain a solid After purification by DCM column chromatography, the 1,7-dicyano-modified peryleneimide derivative represented by the above formula C was obtained. NMR data spectrum see Figure 7 , mass spectrometry data spectrum see Figure 8 .

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Abstract

The invention relates to 1,7-dicyano-modified perylene imide derivatives and a preparation method thereof. Ring opening is performed to increase the solubility of perylene imide, so that the solubility of the perylene imide matrix is enhanced, thereby better introducing the cyano group; and on such basis, the chlorosulfonic acid is added for cyclization to form the required intermediate for preparing the 1,7-dicyano-modified perylene imide derivatives. According to the preparation method, biscyano perylene imide derivatives are firstly synthesized as the intermediate of the constructed unit, and the intermediate reacts with different anilino compounds to obtain the 1,7-dicyano-modified perylene imide derivatives disclosed as the following structural formula. The derivatives have the advantages of excellent weather resistance, favorable solubility and favorable chemical stability, and have wide application range in the fields of dyes, organic semiconductors, liquid crystal materials, organic field effect luminescent materials and the like. The preparation method is simple, efficient, safe and reliable, and is easy to implement.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to derivatives of 1,7-dicyano modified perylene imides and a preparation method thereof. Background technique [0002] As an important class of n-type organic semiconductor materials, perylene imide derivatives are widely used due to their large conjugation plane, high fluorescence quantum yield, excellent electron transport properties and light, thermal and chemical stability. It is used in fluorescent probes, organic field effect transistors, dye industry, gas sensors and medical and biological fields. By introducing different substituents on the bay region and the amide bond, peryleneimide compounds with different aggregation structures and photoelectric properties can be designed and synthesized. [0003] Due to the π-π stacking between molecules, the solubility of diimide is greatly reduced. When it is used as an organic acceptor photovoltaic material and a donor mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06
CPCC07D471/06
Inventor 车延科张义斌赵进才
Owner INST OF CHEM CHINESE ACAD OF SCI
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