Ulllazine derivatives containing diarylboron and diarylamine and synthesis method thereof

A kind of technology of diarylamine and diarylboron, which is applied to a class of Ullazine derivatives containing diarylboron and diarylamine and its synthesis field, can solve the problem that there is no research report on triarylboron and triarylamine, etc. question

Pending Publication Date: 2021-01-29
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Triarylboron and triarylamine are commonly used synthetic materials in the field of optoelectronics, but there are almost no research reports on triarylboron and triarylamine containing Ullazine structure

Method used

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  • Ulllazine derivatives containing diarylboron and diarylamine and synthesis method thereof
  • Ulllazine derivatives containing diarylboron and diarylamine and synthesis method thereof
  • Ulllazine derivatives containing diarylboron and diarylamine and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: the synthesis of compound 4a

[0040]

[0041] 1) Synthesis of compound 2a: Weigh an appropriate amount of 1-(2,6-diethynylphenyl)-1H-pyrrole, tetrakistriphenylphosphine palladium, cuprous iodide, 1-iodobenzene, nitrogen protection, add Anhydrous triethylamine and tetrahydrofuran were refluxed at 80°C for 24h. After the reaction is complete, filter, spin dry with triethylamine, filter with dichloromethane and water, dry over anhydrous magnesium sulfate, and separate by column chromatography after filtration to obtain the yellow target compound 2a.

[0042] 2) Synthesis of compound 3a: add an appropriate amount of compound 2a to a 50mL test tube, add anhydrous toluene under the protection of anhydrous indium trichloride under nitrogen, and react at 110°C for 24 hours. Extracted with methane and water, the organic phase was dried with anhydrous magnesium sulfate, spin-dried, and purified by column chromatography to obtain compound 3a as a yellow solid. ...

Embodiment 3

[0051] Embodiment 3: the synthesis of compound 4b

[0052] 1) Synthesis of compound 2b: Weigh an appropriate amount of 1-(2,6-diethynylphenyl)-1H-pyrrole, tetrakistriphenylphosphine palladium, cuprous iodide, (4-iodophenyl) 4- Iodine-N,N-bis(4-methoxyphenyl)aniline was pumped and ventilated 3 times, under nitrogen protection, anhydrous triethylamine was added and refluxed at 80°C for 24h. After the reaction is complete, filter, spin dry with triethylamine, filter with dichloromethane and water, dry over anhydrous magnesium sulfate, and separate by column chromatography after filtration to obtain the yellow target compound 2b.

[0053] 2) Synthesis of compound 3b: add an appropriate amount of compound 2b to a 50mL test tube, add anhydrous toluene under the protection of anhydrous indium trichloride under nitrogen, and react at 110°C for 24 hours. Extracted with methane and water, the organic phase was dried with anhydrous magnesium sulfate, spin-dried, and purified by column c...

Embodiment 4

[0055] Embodiment 4: the synthesis of compound 5b

[0056]

[0057] 1) Synthesis of compound 2b: Weigh an appropriate amount of 1-(2,6-diethynylphenyl)-1H-pyrrole, tetrakistriphenylphosphine palladium, cuprous iodide, (4-iodophenyl) 4- Iodine-N,N-bis(4-methoxyphenyl)aniline was pumped and ventilated 3 times, under nitrogen protection, anhydrous triethylamine was added and refluxed at 80°C for 24h. After the reaction is complete, filter, spin dry with triethylamine, filter with dichloromethane and water, dry over anhydrous magnesium sulfate, and separate by column chromatography after filtration to obtain the yellow target compound 2b.

[0058] 2) Synthesis of compound 3b: add an appropriate amount of compound 2b to a 50mL test tube, add anhydrous toluene under the protection of anhydrous indium trichloride under nitrogen, and react at 110°C for 24 hours. Extracted with methane and water, the organic phase was dried with anhydrous magnesium sulfate, spin-dried, and purified...

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Abstract

The invention relates to a plurality of Ulllazine derivatives containing diarylboron and diarylamine and a synthesis method thereof. The photoelectric material quantity properties of the compounds aretested, and the potential application values of the compounds in the aspect of organic photoelectricity are further studied. The structural formulas of the compounds are shown in the description, wherein R1 groups are independent and can be single substituted halogen atoms X: F, Cl, Br and I, or hydrogen, olefin, alkyne, alkyl, aldehyde group or ketone, or substituted or unsubstituted aryl and heteroaryl (benzene ring, thiophene ring, furan ring, pyrrole, pyridine, benzothiophene, benzofuran, benzopyrrole, benzopyridine, naphthalene ring, anthracene ring, phenalene, tetracene, pyrene, chrysene, linear or angled pentacene, hexacene, indene, fluorene and the like), or a diarylboron group or a diarylamine group, Ar1 and Ar2 represent different types of aryl groups (benzene ring, thiophene ring, furan ring, pyrrole, pyridine, benzothiophene, benzofuran, benzopyrrole, benzopyridine, naphthalene ring, anthracene ring, phenadiene, tetracene, pyrene, chrysene, linear or angled pentacene, hexacene, indene, fluorene and the like).

Description

technical field [0001] The synthetic method of a class of Ullazine derivatives containing diaryl boron and diarylamine, the 4 bromo-2,6-diiodoaniline that commercially available p-bromoaniline forms by reaction of iodine monochloride is a raw material, through Paal -Knorr reaction, Sonogashira coupling reaction coupling reaction, ring closure reaction catalyzed by indium trichloride, Ullazine containing diarylboron and diarylamine can be obtained by n-butyllithium bromide extraction or Buchwald-Hartwig coupling reaction derivative. The synthesis method has the characteristics of simple operation, mild reaction conditions, short reaction path, etc., and the compound can be applied in the field of organic photoelectric materials. Background technique [0002] Ullazine is a nitrogen-containing heterocyclic ring system with 16π electrons, which is pyrene and other electrons. The π-electron cycloalkene resonance structure composed of concentrated positive charges when the in-pl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/16
CPCC07D471/16
Inventor 刘旭光叶锦程安长华
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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