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Perylene diimide compound, as well as preparation method and application thereof

A perylene imide and compound technology, applied in the field of polymer synthesis, can solve the problems of large charge loss, etc., and achieve the effects of wide absorption, weakened aggregation, and strong absorption

Active Publication Date: 2017-05-10
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But it is easy to form a larger aggregate phase, resulting in a larger charge loss

Method used

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  • Perylene diimide compound, as well as preparation method and application thereof
  • Perylene diimide compound, as well as preparation method and application thereof
  • Perylene diimide compound, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Take 3,3',5,5'-biphenyltetraboronic acid pinacol ester (1.52mmol, 1g), N,N'-bis(2-ethylpropyl)-1-bromo-perylenediimide Amine (8eq, 12.16mmol, 7.41g), 200mg Pd(PPh 3 ) 4 、K 2 CO 3 The mixed solution (containing 200mL toluene, 8mL ethanol, where K 2 CO 3 Concentration is 2mol / L) in a 500mL flask, after passing nitrogen, raise the temperature to 80°C, react for 48h, then dilute the reaction solution with dichloromethane and wash with saturated brine, collect the organic layer and dry it, then remove the dichloromethane by rotary evaporation , and then carried out column chromatography with petroleum ether / dichloromethane as the eluent to obtain 1.9 g of the target product (molecular formula shown in 3a below), with a yield of 54%.

[0026]

Embodiment 2

[0028] Take 3,3',5,5'-biphenyltetraboronic acid pinacol ester (1.52mmol, 1g), N,N'-diisooctyl-1-bromo-7-perylenediimide (8eq , 12.16mmol, 8.43g), 200mg Pd(PPh 3 ) 4 and K 2 CO 3 The mixed solution (containing 200mL toluene, 8mL ethanol, where K 2 CO 3 The concentration is 2mol / L) was placed in a 500mL flask, and after nitrogen was passed through, the temperature was raised to 80°C, and the reaction was carried out for 48h. Then dilute the reaction solution with dichloromethane and wash with saturated brine, collect the organic layer and dry it, then remove the dichloromethane by rotary evaporation and use petroleum ether / dichloromethane as eluent for column chromatography to obtain the compound 3b with the following structural formula ( 2.5 g, 63.2%).

[0029]

Embodiment 3

[0031] Take 3,3',5,5'-biphenyltetraboronic acid pinacol ester (1.52mmol, 1g), N,N'-di(2-pentylhexyl)-1-bromo-perylenediimide (8eq, 12.16mmol, 9.46g), 200mg Pd(PPh 3 ) 4 and K 2 CO 3 The mixed solution (containing 200mL toluene, 8mL ethanol, where K 2 CO 3 The concentration is 2mol / L) was placed in a 500mL flask, and after nitrogen was passed through, the temperature was raised to 80°C, and the reaction was carried out for 48h. Then dilute the reaction solution with dichloromethane and wash with saturated brine, collect the organic layer and dry it, then remove the dichloromethane by rotary evaporation and use petroleum ether / dichloromethane as eluent for column chromatography to obtain the compound 3c (3.09g , 73.2%).

[0032]

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Abstract

The invention relates to a perylene diimide compound and a preparation method thereof. The perylene diimide compound has a structural formula shown in formula (1), wherein R is an alkyl group; X is one of H, cyanogroup and an alkoxy group. The preparation method comprises the following steps: mixing biphenyl tetraborate ester and 1-bromo-perylene diimide according to a molar ratio of 1:(5-8), adding K2CO3 and Pd(PPh3)4 as catalysts in a nitrogen atmosphere, and performing Suzuki coupling reaction to obtain the perylene diimide compound at 60 to 90 DEG C by adopting toluene and ethanol as solvents. A provided perylene diimide small molecule has a relatively large conjugated structure and three-dimensional structure, and is high in electron mobility and synthesis yield and suitable for large-scale production, multidimensional charge transport can be realized, and an adopted biphenyl core is low in cost and high in reactivity.

Description

technical field [0001] The invention belongs to the technical field of polymer synthesis, and relates to a perylene imide compound and a preparation method and application thereof. Background technique [0002] With the gradual depletion of petroleum and other energy sources, the development and application of renewable energy such as solar energy has gradually become the focus of social attention. The main way to utilize solar energy is to develop solar cells. However, traditional silicon-based solar cells are expensive, have a long energy repayment time, complex preparation procedures, and are prone to pollution during the production process. In comparison, organic solar cells and perovskite solar cells have the incomparable advantages of silicon-based solar cells, such as light weight, low price, easy processing, and large-area devices, and are increasingly valued by relevant researchers. [0003] Perylene imide compounds have great potential when applied to solar cells....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/42H01L51/46
CPCC07D519/00H10K85/6572H10K30/00H10K2102/00Y02E10/549
Inventor 刘治田吴瑶高翔张林骅於凌峰张旗
Owner WUHAN INSTITUTE OF TECHNOLOGY
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