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
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[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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