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Small molecules containing seven-membered ring diimides and their derivatives, preparation methods and applications

A technology of cyclodiimide and cyclobiphenylimide, which is applied in the field of chemical synthesis of imide conjugated polymers, can solve the problems of difficult expansion of polymer synthesis and application, and many synthesis steps. Good redox properties, increased solubility, and reasonable design of the process route

Active Publication Date: 2022-02-25
CHANGAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this system has many synthetic steps, and it is difficult to extend it to the synthesis and application of corresponding polymers.

Method used

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  • Small molecules containing seven-membered ring diimides and their derivatives, preparation methods and applications
  • Small molecules containing seven-membered ring diimides and their derivatives, preparation methods and applications
  • Small molecules containing seven-membered ring diimides and their derivatives, preparation methods and applications

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preparation example Construction

[0104] 1. Preparation of imide compounds

[0105] 1) Preparation of compound 1

[0106] Dissolve pyrene in dichloromethane, acetonitrile and water, then add solid sodium periodate and ruthenium trichloride catalyst. The molar ratio of pyrene, dichloromethane, acetonitrile, water, sodium periodate and ruthenium trichloride is: 1:200:200:300:(0.01-0.1). React at room temperature for 24 hours, filter, extract the filter cake with acetone, filter, collect the filtrate, remove the orange solid from the solvent, reflux in dichloromethane for 2 hours, remove the solution by filtration while it is hot, dissolve the solid in a small amount of absolute ethanol, and then add a large amount of n-Hexane, white precipitate, colorless transparent crystal recrystallized in hot water. Its reaction equation is as follows:

[0107]

[0108] 2) Preparation of compound 2

[0109] Under argon atmosphere, add 10 mmol of compound 1 into a two-necked flask containing 20 mL of dry acetic anhydri...

Embodiment 1

[0162] The preparation of seven-membered ring diimide small molecules and macromolecules comprises the following steps:

[0163] 1) Synthesis of compound 1

[0164] Dissolve 10g of pyrene in 200mL of dichloromethane, then add 200mL of acetonitrile and 300ml of water, stir and dissolve, then add 100g of solid sodium periodate and 40mg of ruthenium trichloride catalyst. React at room temperature for 24 hours, filter, extract the filter cake with 1000 mL of acetone, filter, collect the filtrate, remove the orange solid from the solvent, reflux in dichloro for 2 hours, remove the solution by filtration while hot, dissolve the solid in a small amount of absolute ethanol, and then add A large amount of n-hexane precipitates a white precipitate and is a colorless transparent crystal recrystallized in hot water. Wherein the molar ratio of pyrene, sodium periodate and ruthenium trichloride is 1:9.4:0.04.

[0165] 2) Synthesis of Compound 2

[0166] Under the protective atmosphere of...

Embodiment 2

[0188] According to the method for synthesizing the target product 1 in Example 1, aniline was replaced by methylamine, and other steps in this step were the same as those in the corresponding Example 1.

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Abstract

The present invention discloses a class of small molecules containing brominated diimides containing seven-membered rings. Based on this type of small molecules with active sites, a series of novel polyimide polymers are synthesized, and their corresponding photoelectric properties are studied. nature. And use this polymer material as the anode material of organic battery to explore its application in lithium ion button battery. The invention designs and synthesizes the small molecules and polymers of conjugated bromoimides containing double seven-membered rings for the first time. This new type of imide compound exhibits unique photoelectric properties and good redox properties due to its unique twisted structure. Therefore, one class of small molecules exhibits the rare phenomenon of aggregation-induced blue shift (AIBSE). The preparation method of the imide compound of the invention is easy to operate and has mild reaction conditions; the prepared lithium ion battery has good rate performance and cycle stability, and is a negative electrode material with excellent performance in organic lithium ion batteries. The invention not only makes up for the deficiency of imide material structure types, but also broadens its application in organic battery materials.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis of imide conjugated polymers, and specifically relates to a class of small molecules containing imides containing seven-membered rings and their derivatives, preparation methods and applications. Background technique [0002] Polyimide is an aromatic heterocyclic polymer material with imide ring repeating units in the main chain. The unique aromatic heterocyclic structure endows imide with excellent properties, such as excellent high temperature resistance and low temperature resistance, good It has excellent comprehensive properties such as excellent electrical insulation properties, outstanding mechanical properties, unique optical properties, aging resistance, radiation resistance, and solvent resistance. Today, polyimide materials are mainly used as materials such as plastics, fibers and films, and are widely used in coatings, adhesives, aerospace, automotive industry, electronic an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/06C08G61/12C08G73/10H01L51/46H01L51/48
CPCC07D487/06C08G61/126C08G73/1007C08G73/1067C08G2261/3223C08G2261/3241C08G2261/124C08G2261/1412C08G2261/18C08G2261/411C08G2261/414C08G2261/3328C07B2200/13H10K71/12H10K85/151
Inventor 晏妮何刚王之君
Owner CHANGAN UNIV
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