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Method for preparing binary perylene diimide derivative efficiently

A compound and selected technology, applied in the direction of organic chemistry, can solve the problems of many by-products, long reaction time, environmental pollution materials, etc., achieve the effect of easy separation and purification, cheap raw materials, and expand the scope of application

Active Publication Date: 2013-08-14
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Based on the reported patents, it can be seen that the synthesis of the parent skeleton of bis-perylenediimide is not easy: organic synthesis methods are extremely limited, and no efficient synthetic route has been developed so far; the reaction yield is very low, usually below 15%, which is not conducive to industrial scale-up Production; harsh reaction conditions, high requirements on the purity of reaction materials, very sensitive to oxygen and water, and poor repeatability; long reaction time and long production cycle, which cannot meet high-efficiency production; a large amount of reaction raw materials are left, and there are many by-products, which are extremely unfavorable for separation and purification, it is easy to cause a lot of environmental pollution and material loss due to post-processing

Method used

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  • Method for preparing binary perylene diimide derivative efficiently
  • Method for preparing binary perylene diimide derivative efficiently
  • Method for preparing binary perylene diimide derivative efficiently

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1, preparation C4-4CldiPBI (2a) (R=C in the formula I 4 h 9 , X=Cl compound)

[0033] In a 100mL two-necked round-bottom flask, evacuate and ventilate with argon. Then add tetrachloroperylene diimide raw material (1a) (R=C in the formula II 4 h 9 , X=Cl compound) (1.28g, 2.0mmol), cuprous iodide (0.95g, 5.0mmol), potassium thiophene-2-carboxylate (0.83g, 5.0mmol), potassium tert-butoxide (0.56g, 5.0 mmol). Dimethyl sulfoxide (40 mL) was injected at room temperature, and stirred at 90° C. for 12 h. Stop heating, cool naturally, pour the reaction mixture into 200mL deionized water, and stir well. Filter the above mixed solution with a Buchner funnel, and wash the filter cake with 100 mL of saturated ammonia water to remove a large amount of copper ions. The filter cake was washed with 300 mL of deionized water, 100 mL of anhydrous methanol, and dried at 100°C. Finally, the filter cake was dissolved in 100 mL of dichloromethane, mixed with diatomaceous e...

Embodiment 2

[0039] Embodiment 2, preparation C4-4CldiPBI (2a)

[0040] The preparation method was basically the same as in Example 1, except that the stirring at 90°C for 12 hours was replaced by stirring at 70°C for 15 hours in Example 1 to obtain 0.43 g of a purple-black solid (yield: 38%).

Embodiment 3

[0041] Embodiment 3, preparation C4-4CldiPBI (2a)

[0042]The preparation method was basically the same as that in Example 1, except that the stirring at 90°C for 12 hours in Example 1 was replaced by stirring at 120°C for 8 hours to obtain 0.35 g of a purple-black solid (yield: 31%).

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Abstract

The invention discloses a method for preparing binary perylene diimide derivative efficiently. The structural general formula of a compound is shown in the formula I. The preparation method comprises the following steps of: in inert atmosphere, carrying out reaction on the compound shown by a formula II, a copper catalyst, organic small molecule ligand and an organic base so as to obtain the compound shown in the formula I. The method has the advantages of being simple and efficient, light in environment contamination, cheap in raw material price, low in synthesis cost, good in universality and repeatability and the like, and can be promoted and used for synthesis of various other N substituent group binary perylene diimide derivative.

Description

technical field [0001] The invention relates to a method for preparing bisperylenediimide derivatives. Background technique [0002] Perylene diimide derivatives are a common class of industrial pigments, widely used in industrial fields such as dyes and coatings. With the continuous development of material science, perylene diimide derivatives have been endowed with new properties and applications, and their photoelectric properties have become increasingly prominent, so they have an important position and application prospects in the field of organic photoelectric materials. For example, the field of organic semiconductors includes organic field-effect transistors, organic light-emitting diodes, and organic photovoltaic materials. Among them, organic field-effect transistor materials have attracted the attention of the semiconductor industry due to their excellent semiconductor properties. Researchers have prepared a series of perylene diimide derivatives through differen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/22
Inventor 胡文平卢修强甄永刚邵伟黄贤良李源基
Owner INST OF CHEM CHINESE ACAD OF SCI
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