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Method for preparing diketopyrrolopyrrole organic materials with terminals substituted by dye units

A technology of diketopyrrolopyrrole and organic materials, applied in the field of synthesis of organic conjugated small molecules, which can solve problems such as difficult large-scale production, hazards of chloroform solvents, skin irritation, etc., achieve low toxicity, reduce energy consumption, and facilitate operation Effect

Inactive Publication Date: 2018-09-21
YANCHENG TEACHERS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Both chloroform and piperidine are highly toxic chemicals, among which chloroform is also a precursor drug. It may irritate the skin, oral mucosa, respiratory organs and eyes as a solvent, and is oxidized by oxygen in the air to generate highly toxic phosgene. Narcotic and carcinogenic are reagents controlled by the public security department, so the use of chloroform solvents is more harmful
Moreover, similar preparation reactions require the system to be heated to reflux and kept in an inert gas atmosphere, making it difficult to carry out large-scale production

Method used

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  • Method for preparing diketopyrrolopyrrole organic materials with terminals substituted by dye units
  • Method for preparing diketopyrrolopyrrole organic materials with terminals substituted by dye units

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add compound 1 (0.2 mmol, 116 mg) and 3-ethylrhodanine (1.0 mmol, 161 mg) in a molar ratio of 1:5 in a 50 mL round bottom flask, add 20 mL of dichloromethane and 0.02 mmol of tris Ethylamine was kept at room temperature for 10 hours. After the reaction, the system was washed three times with water, and the organic phase was washed with anhydrous MgSO 4 After drying, the solvent was removed, and the crude product was recrystallized from a solution of dichloromethane and methanol at a volume ratio of 20:1 to obtain a purple solid powder product with a yield of 65%.

Embodiment 2

[0019] Add compound 1 (0.2 mmol, 116 mg) and 3-ethylrhodanine (2.0 mmol, 322 mg) in a molar ratio of 1:10 in a 50 mL round bottom flask, add 20 mL of dichloromethane and 0.02 mmol of tris Ethylamine was kept at room temperature for 10 hours. After the reaction, the system was washed three times with water, and the organic phase was washed with anhydrous MgSO 4 After drying, the solvent was removed, and the crude product was recrystallized from a solution of dichloromethane and methanol at a volume ratio of 20:1 to obtain a purple solid powder product with a yield of 87%.

Embodiment 3

[0021] Add compound 1 (0.2 mmol, 116 mg) and 3-ethylrhodanine (4.0 mmol, 644 mg) in a molar ratio of 1:20 in a 50 mL round bottom flask, add 20 mL of dichloromethane and 0.02 mmol of tris Ethylamine was kept at room temperature for 10 hours. After the reaction, the system was washed three times with water, and the organic phase was washed with anhydrous MgSO 4 After drying, the solvent was removed, and the crude product was recrystallized from a solution of dichloromethane and methanol at a volume ratio of 20:1 to obtain a purple solid powder product with a yield of 90%.

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Abstract

The invention provides a method for preparing diketopyrrolopyrrole organic materials with terminals substituted by dye units. The diketopyrrolopyrrole organic materials are made from thienyl diketopyrrolopyrrole dialdehyde and 3-ethyl rhodanine. The method includes adding a certain quantity of solvents into the thienyl diketopyrrolopyrrole dialdehyde and the 3-ethyl rhodanine and then dropwise adding organic amine into the thienyl diketopyrrolopyrrole dialdehyde and the 3-ethyl rhodanine; carrying out reaction at the certain temperatures for a period of time; washing and drying reaction products after the reaction is completely carried out and removing a solvent; re-crystallizing crude products to obtain the diketopyrrolopyrrole organic materials which are target products. The organic amine is used as a catalyst. The method has the advantages that low-toxicity dichloromethane is used as the solvent instead of trichloromethane, and accordingly the problems of controlled pharmaceutical procurement and treatment can be solved; the method can be carried out under room-temperature conditions, energy consumption can be reduced as compared with disclosed heating reflux conditions, accordingly, energy can be saved, environments can be protected, the method has a high safety coefficient, equipment is simple and is convenient to operate, special anhydrous and anaerobic treatment and thelike for reaction systems can be omitted, rigorous reaction conditions can be omitted, and the method is suitable for large-scale production and industrial application.

Description

technical field [0001] The invention relates to the field of synthesis of organic conjugated small molecules, and relates to a preparation method of a diketopyrrolopyrrole organic material substituted with a terminal dye unit. Background technique [0002] Organic optoelectronic materials have a π-conjugated molecular structure and excellent electron delocalization performance, diverse structural composition and performance adjustment space, and can adjust the light absorption performance, optical band gap, and orbital energy level of the material through different combinations of donor and acceptor units. etc., thus being widely used in fields such as organic light emitting diodes, field effect transistors and solar cells. The dye unit diketopyrrolopyrrole (DPP) molecular skeleton has attracted extensive attention due to its bright colors and excellent stability, and the DPP skeleton can adjust the optical absorption properties and orbital energy levels of materials through...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 邢蓉孙世新方东
Owner YANCHENG TEACHERS UNIV
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