Fused ring aromatic imide derivative compound, preparation method and applications thereof

A technology of fused-ring aromatic imides and derivatives, which is applied in the field of fused-ring aromatic imide derivatives and their preparation, can solve the problems of simple coordination form, single coordination point, single structure and function, etc. Achieve the effect of simple purification, simple operation and high yield

Inactive Publication Date: 2020-02-21
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, monodentate ligands are usually used. However, such ligands have a single coordination site and a simple coordination form, and the structure and function of the obtained complexes are single. Functional ligands to obtain fused-ring aromatic imide derivatives with rich coordination forms, diversified functions and outstanding performance

Method used

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  • Fused ring aromatic imide derivative compound, preparation method and applications thereof
  • Fused ring aromatic imide derivative compound, preparation method and applications thereof
  • Fused ring aromatic imide derivative compound, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] This embodiment provides a fused-ring aromatic imide derivative compound, the structural formula of which is:

[0035]

[0036] The synthetic route for preparing compound I-1 is as follows:

[0037]

[0038] Specific steps are as follows:

[0039] Under nitrogen protection, pyromellitic anhydride (4.58mmol) was refluxed in anhydrous N,N-dimethylacetamide (50mL) for 5min; 3-aminopyrazole (9.16mmol) was dissolved in anhydrous N,N -Dimethylacetamide (5mL) was then injected into the reaction flask with a syringe; the mixture was stirred and refluxed for 6h; the reaction was completed, cooled to room temperature, filtered with suction, the filter cake was washed with dichloromethane, and dried in vacuo to obtain compound I-1, Yield 91%;

Embodiment 2

[0041] This embodiment provides a fused-ring aromatic imide derivative compound, the structural formula of which is:

[0042]

[0043] The synthetic method for preparing compound I-2 is the same as that of Example 1, except that 3-aminopyrazole is replaced by 5-methyl-3-aminopyrazole; the yield of compound I-2 is 89%.

Embodiment 3

[0045] This embodiment provides a fused-ring aromatic imide derivative compound, the structural formula of which is:

[0046]

[0047] The synthetic route for preparing compound II-1 is as follows:

[0048]

[0049] Specific steps are as follows:

[0050] Under nitrogen protection, 1,4,5,8-naphthalene tetracarboxylic anhydride (3.2mmol), 3-aminopyrazole (6.8mmol) were refluxed in anhydrous N,N-dimethylformamide (50mL) for 9h; After the reaction was completed, cool to room temperature, pour the solution into diethyl ether (150mL), filter with suction, recrystallize the filter cake with N,N-dimethylformamide / diethyl ether (20mL / 30mL), filter and dry in vacuo to obtain compound II- 1. The yield is 82%;

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Abstract

The invention relates to the field of compounds, particularly to a fused ring aromatic imide derivative compound, a preparation method and applications thereof, wherein the fused ring aromatic imide derivative compound has a structure as shown in a formula I or a formula II or a formula III, and R is one selected from 3-pyrazole, 4-pyrazole and 5-methyl-3-pyrazole. According to the invention, thefused ring aromatic imide derivative compound is prepared by using a simple organic synthesis method, and can be applied to the fields of coordination chemistry, solar cells, light emitting diodes, biochemistry and the like; the preparation method has few steps, can obtain the product through one-step synthesis, is simple in operation, only involves common organic synthesis steps, and has characteristics of low production cost, cheap and easily available raw materials, high yield and simple post-treatment purification, wherein the yield is more than 80%; and the preparation method is suitablefor industrial production of fused ring aromatic imide derivative compounds.

Description

technical field [0001] The invention relates to the field of compounds, in particular to a condensed-ring aromatic imide derivative compound and its preparation method and application. Background technique [0002] Fused-ring aromatic imide derivatives contain a rigid planar large conjugated system structure and have unique photoresponse properties. They are an excellent class of chromophores with excellent chemical and photothermal stability, high molar absorptivity and Electron mobility is a good photoelectric material, showing good application prospects in solar cells, organic light-emitting diodes, fluorescent sensors, and anti-tumor drugs. In recent years, the design and synthesis of fused-ring aromatic imide derivatives with good and unique properties is one of the important research directions in the field of chemical research. [0003] In the prior art, monodentate ligands are usually used. However, such ligands have a single coordination site and a simple coordinat...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D487/06H01L51/54H01L51/42
CPCC07D487/04C07D487/06H10K85/654H10K85/6572Y02E10/549Y02P70/50
Inventor 于澍燕路红琳童金
Owner BEIJING UNIV OF TECH
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