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1, 6-disubstituted perylene diimide compound as well as synthesis method and application thereof

A technology of perylene diimide and synthesis method, which is applied in the field of 1,6-disubstituted perylene diimide compound and its synthesis, can solve problems such as difficulties in the synthesis of a large number of perylene diimide compounds, and achieve good industrial application Prospects, high photoelectric conversion efficiency, and easy-to-obtain raw materials

Active Publication Date: 2022-03-18
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of this, it is necessary to provide a 1,6-disubstituted perylenediimide compound and its synthesis method and application, in order to solve the difficulties in the synthesis of a large number of 1,6-disubstituted perylenediimide compounds in the prior art technical issues

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  • 1, 6-disubstituted perylene diimide compound as well as synthesis method and application thereof
  • 1, 6-disubstituted perylene diimide compound as well as synthesis method and application thereof
  • 1, 6-disubstituted perylene diimide compound as well as synthesis method and application thereof

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preparation example Construction

[0038] The second aspect of the present invention provides a kind of synthetic method of 1,6-disubstituted perylene diimide compound, comprising the following steps:

[0039] S1. React compound 1 with anhydrous methanol under the action of the first base and the first organic solvent to obtain compound 2; wherein, the molar ratio of compound 1 to anhydrous methanol is 1: (10-90), further 1 : (80~90), further being 1:85; the first base is selected from anhydrous potassium carbonate, anhydrous sodium carbonate, anhydrous potassium acetate, anhydrous cesium carbonate, anhydrous sodium acetate, anhydrous potassium phosphate At least one, the molar ratio of compound 1 to the first base is 1: (0.3-4), further 1: (2.5-3) and further 1:3; the first organic solvent is selected from N-methylpyrrolidone (NMP ), toluene, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, the amount ratio of compound 1 to the first organic solvent is 1g: (8~ 15)ml, further 1g: 10mL; the rea...

Embodiment 1

[0053] Synthesis of 1,6-diMeOPDI:

[0054] (1) Add 1.2g of compound 1a and 600mg of anhydrous potassium carbonate into a microwave reaction flask, then add 5mL of anhydrous MeOH and 12mL of anhydrous NMP, heat to 100°C in a microwave reactor, and stop the reaction after 1h. The reactant was poured into 100mL dilute hydrochloric acid, the solid obtained by suction filtration was washed with water, dried and separated by column chromatography to obtain 423.4 mg of compound 2a (40% yield). The hydrogen spectrum and mass spectrum of compound 2a are shown in Figure 1~2 .

[0055] (2) Add compound 2a (320mg), palladium acetate (10mg), n-butyl bis (1-adamantyl) phosphine (32mg), anhydrous potassium carbonate (122mg), 7-tridecylamine in the autoclave (176mg) and toluene (15mL) were assembled into a reaction vessel, deoxygenated with nitrogen, and filled with 1MPa carbon monoxide gas, and the reactants were heated to 110°C for 3h. After the toluene was removed by the rotary evaporat...

Embodiment 2

[0059] Synthesis of 1,6-diHOPDI:

[0060] Add 80mg of 1,6-diMeOPDI to a 100ml two-necked bottle, pump nitrogen for 30min, add 5mL of dichloromethane to remove water and deoxygenate, lower it to 0°C and slowly add 0.3mL of boron tribromide in hexane alkane solution (1M), gradually warmed up to 25°C and stirred for 10 hours, slowly poured into 200mL of water after the reaction, extracted with dichloromethane, separated and purified the organic layer after drying to obtain purple red compound 4a (1,6-diHOPDI) (54 mg, 70%).

[0061] Concrete reaction formula is as follows:

[0062]

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Abstract

The invention relates to a 1, 6-disubstituted perylene diimide compound as well as a synthesis method and application thereof, the compound has the following structural formula: wherein R1 is selected from substituted or unsubstituted C1-C30 alkyl; and R2 is selected from a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted sulfonic acid group, and a substituted or unsubstituted perylene diimide group. The 1, 6-disubstituted perylene diimide compound is directly obtained through a synthesis means for the first time, the synthesis route is simple, raw materials are easy to obtain, and the 1, 6- / 1, 7-isomerization problem of perylene diimide is fundamentally solved; meanwhile, an organic solar device test shows that high photoelectric conversion efficiency can be obtained by using the 1, 6-bit disubstituted perylene diimide molecular material as a semiconductor material, the device is optimized by adjusting a modification group again in the later period, a solar cell with higher photoelectric conversion efficiency can be expected to be obtained, and the 1, 6-bit disubstituted perylene diimide molecular material has a good industrial application prospect.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a 1,6-disubstituted perylene diimide compound and its synthesis method and application. Background technique [0002] Perylene diimides (PDI) material molecules are often used to construct n-type organic semiconductor materials because of their cheap and readily available raw materials, easy functionalization, good photoelectric performance and low LUMO energy level. . With the joint efforts of researchers in the research fields of synthetic chemistry, material chemistry, and device physics, PDI-based organic semiconductor materials have made great progress and have shown good application prospects. On this basis, the design and synthesis of new high-performance PDI material molecular systems can provide strong theoretical guidance and experimental basis for the further development of PDI materials, and this is also a research hotspot and frontier in rela...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C07D519/00H01L51/46
CPCC07D471/06C07D519/00H10K85/6572Y02E10/549
Inventor 夏建龙邵光伟吴迪吴明亮王东雪
Owner WUHAN UNIV OF TECH