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Synthesis method of azafluorene spiro aromatic hydrocarbon

A technology of spiroaromatics and synthesis methods, which is applied in the field of efficient preparation of preparation methods, can solve the problems of long synthetic routes, inability to directly prepare azafluorene spiroaromatics with flexible substituents, limited expansion of substrates, etc., and achieve low cost , easy industrial production, simple operation

Active Publication Date: 2016-09-07
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Yet this method has following shortcoming: (1) synthetic route is longer
(2) The scope of substrate expansion is very limited, and it is impossible to directly prepare azafluorene spiro aromatic hydrocarbons with flexible substituents and phenolic hydroxyl groups

Method used

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  • Synthesis method of azafluorene spiro aromatic hydrocarbon
  • Synthesis method of azafluorene spiro aromatic hydrocarbon
  • Synthesis method of azafluorene spiro aromatic hydrocarbon

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0039] Example 1: Preparation of 3a with azafluorenone and 1-naphthol as raw materials

[0040]

[0041] First add azafluorenone 1a (0.18g, 1mmol), dichlorobenzene 2ml and methanesulfonic acid (0.26ml, 4mmol) to the reaction flask in sequence, keep stirring at 35°C for about 30min, then add 1-naphthol (0.36g, 2.5mmol), the reaction temperature was raised to 150°C for a period of time, and the raw materials were basically reflected by thin-layer chromatography monitoring. Cool and stand, add saturated potassium carbonate solution to the reaction flask to quench the reaction. Pour the mixed solution into potassium carbonate solution or deionized water, extract with dichloromethane, collect the organic phase (dichloromethane extract), dry with anhydrous sodium sulfate, remove the desiccant by suction filtration, and distill off the solvent under reduced pressure, the crude product Azafluorene spiroarene 3a (0.21 g, 50%) with high purity can be obtained by silica gel column ch...

example 2

[0042] Example 2: Preparation of 3b with azafluorenone and p-bromophenol as raw materials

[0043]

[0044]First add azafluorenone 1a (0.18g, 1mmol), dichlorobenzene 2ml and methanesulfonic acid (0.26ml, 4mmol) to the reaction flask in sequence, keep stirring at 35°C for about 30min, then add p-bromophenol ( 0.43g, 2.5mmol), the reaction temperature was increased to 150°C for a period of time, and the raw materials were basically reflected by thin-layer chromatography monitoring. Cool and stand, add saturated potassium carbonate solution to the reaction flask to quench the reaction. Pour the mixed solution into potassium carbonate solution or deionized water, extract with dichloromethane, collect the organic phase (dichloromethane extract), dry with anhydrous sodium sulfate, remove the desiccant by suction filtration, and distill off the solvent under reduced pressure, the crude product Azafluorene spiroarene 3b (0.20 g, 41%) with high purity can be obtained by silica gel ...

example 3

[0045] Example 3: Preparation of 3c with azafluorenone and p-bromophenol as raw materials

[0046]

[0047] First add azafluorenone 1a (0.18g, 1mmol), dichlorobenzene 2ml and methanesulfonic acid (0.26ml, 4mmol) to the reaction flask in sequence, keep stirring at 35°C for about 30min, then add p-bromophenol ( 0.43g, 2.5mmol), the reaction temperature was increased to 150°C for a period of time, and the raw materials were basically reflected by thin-layer chromatography monitoring. Cool and stand, add saturated potassium carbonate solution to the reaction flask to quench the reaction. Pour the mixed solution into potassium carbonate solution or deionized water, extract with dichloromethane, collect the organic phase (dichloromethane extract), dry with anhydrous sodium sulfate, remove the desiccant by suction filtration, and distill off the solvent under reduced pressure, the crude product Azafluorene spiroarene 3c (0.17g, 43%) with high purity can be obtained by silica gel ...

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Abstract

The invention provides a synthesis method of azafluorene spiro aromatic hydrocarbon, and relates to the field of organic semiconductor material synthesis. According to the synthesis method, azafluorenone and a phenolic derivative are adopted as reaction substrates; a reaction is carried out for 12-16h under a temperature of 25-160 DEG C under acid catalysis; through a cationic relay tandem reaction, poly-substituted or poly-functionalized azafluorene spiro aromatic hydrocarbon is synthesized in one step with high efficiency. The acid catalysis is at least one or a combination of: acetic acid, hydrochloric acid, hydrobromic acid, periodic acid, methanesulfonic acid, concentrated sulfuric acid, trifluoromethanesulfonic acid, Eaton reagent, and trifluoroacetic acid hydrofluoric acid-antimony pentafluoride. The dosing molar ratio of the reaction substrate azafluorenone 1 to phenol 2 to the acid catalyst is 1:2-5:3-12. The method has the advantages of easy-to-obtain raw materials, simple operation, high yield, atomic economy and the like. The method is suitable for both laboratory small-scale synthesis and industrialization. The method has a good application prospect.

Description

technical field [0001] The invention belongs to the field of preparation of organic semiconductor materials, and in particular relates to a novel high-efficiency preparation method of azafluorene spiro aromatic hydrocarbons. Background technique [0002] Azafluorene spiroarenes are very important molecular building blocks in the field of organic / plastic electronics. It not only inherits the advantages of electron acceptor, metal coordination, protonation and C-N··H bond of azafluorene, but also retains the basic properties of spiro aromatic hydrocarbons such as conjugation interruption, cross conformation and steric hindrance. . The development of the above-mentioned advantages of azafluorene spiroarenes can be applied to organic electroluminescence, solar cells, organic sensing, supramolecular functional materials, and transition metal catalyzed reactions, so it has attracted extensive attention. [0003] So far, the synthesis method of azafluorene spiro aromatic hydrocar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/20
CPCC07D491/20
Inventor 解令海魏颖林冬青黄浩黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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