4,4'-diamido-4''-ferrocenyl triphenylamine and preparation method thereof

A technology of ferrocenyl aniline and ferrocenyl, which is applied in the field of bisaminoaromatic organic compounds and their preparation, and achieves the effects of simple operation, simple synthesis process and novel structure

Active Publication Date: 2013-02-13
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • 4,4'-diamido-4''-ferrocenyl triphenylamine and preparation method thereof
  • 4,4'-diamido-4''-ferrocenyl triphenylamine and preparation method thereof
  • 4,4'-diamido-4''-ferrocenyl triphenylamine and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0035] a) Preparation of 4,4'-dinitro-4"-ferrocenyltriphenylamine:

[0036] In a 100ml single-necked flask equipped with reflux condensation and a magnet, add 2.21g of 4-ferrocenylaniline, 2.26g of p-nitrofluorobenzene and 4.42g of anhydrous potassium carbonate, and add 30ml of DMSO as a solvent, and start the magnetic stirring and condensed water, and heated to 130°C with a constant temperature oil bath, reacted for 24 hours, cooled to room temperature after the reaction, poured the reaction solution into 800ml deionized water and precipitated for 24 hours, poured off the supernatant, and obtained a dark red viscous Precipitate. Purified by column separation method, the eluent is ethyl acetate and petroleum ether, the ratio is 1:5, after being concentrated by rotary evaporation, it is dried in a vacuum oven at 60°C for 12 hours, and the red solid powder is obtained as the final product 4,4' - Dinitro-4"-ferrocenyltriphenylamine. The mass of product obtained was 2.90 g.

[0...

Embodiment 2

[0042] a) Preparation of 4,4’-dinitro-4”-ferrocenyltriphenylamine

[0043] In a 250ml single-necked flask equipped with reflux condensation and a magnet, add 6.9g of 4-ferrocenylaniline, 10.58g of p-nitrofluorobenzene and 20.7g of anhydrous potassium carbonate, and add 100ml of DMSO as a solvent, and start the magnetic stirring and condensed water, and heated to 150°C with a constant temperature oil bath to react for 48 hours, cooled to room temperature after the reaction, poured the reaction solution into 1600ml deionized water and precipitated for 24 hours, poured off the supernatant, and obtained a dark red viscous precipitation. Purified by column separation method, the eluent is ethyl acetate and petroleum ether, the ratio is 1:5, after being concentrated by rotary evaporation, it is dried in a vacuum oven at 60°C for 12 hours, and the red solid powder is obtained as the final product 4,4' -Dinitro-4 "-ferrocenyl triphenylamine. The product quality obtained is 9.76g;

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Embodiment 3

[0049] a) Preparation of 4,4'-dinitro-4"-ferrocenyltriphenylamine:

[0050] In a 100ml single-necked flask equipped with reflux condensation and a magnet, add 2.21g of 4-ferrocenylaniline, 2.26g of p-nitrofluorobenzene and 3.65g of cesium fluoride, and add 30ml of DMF as a solvent, start magnetic stirring and Condensed water, heated to 130°C with a constant temperature oil bath, reacted for 24 hours, cooled to room temperature after the reaction, poured the reaction solution into 800ml deionized water and precipitated for 24 hours, poured off the supernatant, and obtained a dark red viscous precipitation. Purified by column separation method, the eluent is ethyl acetate and petroleum ether, the ratio is 1:5, after being concentrated by rotary evaporation, it is dried in a vacuum oven at 60°C for 12 hours, and the red solid powder is obtained as the final product 4,4' -Dinitro-4 "-ferrocenyltriphenylamine. The quality of the product obtained is 2.84g;

[0051] Yield 68.4%, me...

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Abstract

The invention provides 4,4'-diamido-4''-ferrocenyl triphenylamine and a preparation method of 4,4'-diamido-4''-ferrocenyl triphenylamine, belonging to the technical field of triphenylamine. The preparation method comprises the steps of taking 4-fluoronitrobenzene and 4-aminophenyl ferrocene as raw materials, adding a certain dose of catalyst, reacting for 12-72h at 110-180 DEG C to obtain 4,4'-binitro-4''-ferrocenyl triphenylamine, and then reducing dinitro-compound to 4,4'-diamido-4''-ferrocenyl triphenylamine by using target carbon as the catalyst and hydrazine hydrate as a reducing agent. 4,4'-diamido-4''-ferrocenyl triphenylamine provided by the invention is simple in synthetic process, low in requirements for the equipment, and high in yield, and the compound is not easy to be oxidized during the preparation process, thereby being suitable for mass production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a bisaminoaromatic organic compound containing both a triphenylamine structure and a ferrocene structure and a preparation method thereof. Background technique [0002] Triphenylamine (TPA) and its derivatives have unique free radical properties. As a stable source of free radicals, they can be used to study the properties of other free radicals and multiple free radicals, and can also be used as catalysts for electrochemical reactions and mild selective oxidation reagents, etc. At the same time, due to the conjugation of the lone pair of electrons on the three benzene rings and the nitrogen atoms connecting them, it presents a typical electron-rich large π electron cloud resonance structure, which makes the organic compound containing triphenylamine structure in the group The process of electronuclear transfer and energy level matching usually exhibits typical electron-donating...

Claims

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Application Information

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IPC IPC(8): C07F17/02
Inventor 齐胜利石蕾田国锋武德珍吴战鹏
Owner BEIJING UNIV OF CHEM TECH
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