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Deuterated carbazole compound, preparation method thereof, photoelectric material and medicine

A technology of deuterated carbazoles and substituted carbazoles, applied in the field of organic chemical synthesis, can solve the problems of high production cost, poor group compatibility, complex synthesis process and the like

Pending Publication Date: 2021-06-01
安徽秀朗新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The object of the present invention is to provide a deuterated carbazole compound and its preparation method, photoelectric material and medicine, to solve the existing technology of complex synthesis process, high production cost and poor group compatibility of deuterated carbazole compound question

Method used

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  • Deuterated carbazole compound, preparation method thereof, photoelectric material and medicine
  • Deuterated carbazole compound, preparation method thereof, photoelectric material and medicine
  • Deuterated carbazole compound, preparation method thereof, photoelectric material and medicine

Examples

Experimental program
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Effect test

Embodiment 1

[0041] This embodiment provides a deuterated carbazole compound, the components of which include a carbazole compound, a hydrofluoric acid catalyst, deuterium water, and 1,4-dioxane solvent; wherein, the carbazole compound: the Hydrofluoric acid catalyst: the deuterium water: the mol ratio of the 1,4-dioxane solvent is 1:(0.05-0.1):(20-40):(5-10)

[0042] Specifically, the molecular structural formula of the carbazole compound is:

[0043]

[0044] Wherein, the R1 is any one of hydrogen, methyl, vinyl, and phenyl; the R2, R3 are ester groups, cyano groups, carbonyl groups, hydroxyl groups, alkoxy groups, alkyl groups, tert-butyl groups, bromo , Chlorine, fluorine, iodine, amide, amine, borate, alkynyl, alkenyl, phenyl, heterocyclic aryl. In this embodiment, the carbazole compound is carbazole.

[0045] The deuterium water is high deuterium water, and the deuterium substitution rate is 99.99%.

[0046] The concentration of the fluoric acid catalyst is anhydrous fluoric acid...

Embodiment 2

[0067] This example provides a deuterated carbazole compound, its preparation method, and photoelectric material, which include most of the technical solutions in Example 1, the difference being that the carbazole compound is 3,6-di-tert-butyl Carbazole.

[0068] The embodiment of the present application also provides a preparation method of deuterated carbazole compounds, including the following steps S21)-S25).

[0069] S21) Obtain each component carbazole compound, hydrofluoric acid catalyst, deuterium water and 1,4-dioxane solvent, wherein, the carbazole compound: the hydrofluoric acid catalyst: the deuterium water: the The molar ratio of 1,4-dioxane solvent is 1:(0.05-0.1):(20-40):(5-10).

[0070] The molecular structural formula of described carbazole compound is:

[0071]

[0072] where the R 1 Is any one of hydrogen, methyl, vinyl, phenyl; said R 2 , R 3 Ester, cyano, carbonyl, hydroxyl, alkoxy, alkyl, tert-butyl, bromine, chlorine, fluorine, iodine, amide, ami...

Embodiment 3

[0084] This embodiment provides a deuterated carbazole compound, its preparation method, and a photoelectric material, which include most of the technical solutions in Example 1, the difference being that the carbazole compound is 9-methylcarbazole.

[0085] The embodiment of the present application also provides a preparation method of deuterated carbazole compounds, including the following steps S31)-S35).

[0086] S31) Obtain each component carbazole compound, hydrofluoric acid catalyst, deuterium water and 1,4-dioxane solvent, wherein, the carbazole compound: the hydrofluoric acid catalyst: the deuterium water: the The molar ratio of 1,4-dioxane solvent is 1:(0.05-0.1):(20-40):(5-10).

[0087] The molecular structural formula of described carbazole compound is:

[0088]

[0089] where the R 1 Is any one of hydrogen, methyl, vinyl, phenyl; said R 2 , R 3 Ester, cyano, carbonyl, hydroxyl, alkoxy, alkyl, tert-butyl, bromine, chlorine, fluorine, iodine, amide, amine, bo...

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Abstract

The invention discloses a deuterated carbazole compound, a preparation method thereof and a photoelectric material. The deuterated carbazole compound takes cheap deuterium water as a deuteration raw material, and hydrogen-deuterium exchange reaction is directly performed on the structure of a carbazole compound. The problems of tedious synthesis process and high cost of the deuterated carbazole compound are solved, and meanwhile, 1, 4-dioxane is used as a solvent, the use of an expensive deuterated reagent as a solvent is avoided, cheap fluorine-containing acid is used as a catalyst, the use of an expensive catalyst is avoided, and the method is low in price, efficient, free of pollution and suitable for industrial production.

Description

technical field [0001] The application relates to the field of organic chemical synthesis, in particular to a deuterated carbazole compound, a preparation method thereof, a photoelectric material and a medicine. Background technique [0002] The replacement of hydrogen atoms in biomolecules or material molecules by deuterium atoms can significantly change the physical, chemical and biological properties of the original molecules. Therefore, deuterated compounds are widely used in the fields of pharmaceutical science, material science, biological science, nuclear science, food science and organic matter identification. [0003] In the field of pharmaceutical design, after the hydrogen in the drug molecule is replaced by deuterium, the metabolic stability of the drug molecule can be improved without changing the targeting of the drug molecule. Therefore, deuterium generation technology is considered as a shortcut to develop new drugs, which is favored by major pharmaceutical ...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D209/88
CPCC07D209/86C07D209/88C07B2200/05
Inventor 李恩赐张宏海税新凤白景文
Owner 安徽秀朗新材料科技有限公司
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