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Benzoyl-modified aggregation-induced emission type aniline oligomer and preparation method thereof

A technology of aggregation-induced luminescence and benzoyl group, which is applied in the preparation of carboxylic acid amides, the preparation of organic compounds, luminescent materials, etc., to achieve the effect of easy control, simple synthesis route, and solving the effect of aggregation-induced quenching

Active Publication Date: 2020-05-15
BEIHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention prepares a class of benzoylaniline-containing oligomer derivatives, uses aniline oligomers and acid chloride homologues as initial reactants, and connects benzamide on the aniline oligomers to obtain a novel benzoylaniline-containing oligomer derivative It solves the problem of aggregation-induced quenching of traditional aniline oligomers, making it have the characteristics of aggregation-induced luminescence

Method used

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  • Benzoyl-modified aggregation-induced emission type aniline oligomer and preparation method thereof
  • Benzoyl-modified aggregation-induced emission type aniline oligomer and preparation method thereof
  • Benzoyl-modified aggregation-induced emission type aniline oligomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Aniline dimer derivative C 2 -A 2 preparation of

[0052] Aniline dimer derivative C 2 -A 2 The synthetic route of is as follows:

[0053]

[0054] Specifically include the following steps:

[0055] Step 101: Weigh 1g of N,N'-diphenyl-1,4-p-phenylenediamine and place it in a 100ml three-neck flask, add 3ml of pyridine as an acid-binding agent and 20ml of chloroform as a solvent to fully dissolve to obtain a solution ;

[0056] Step 102: Measure 6ml of benzoyl chloride, dissolve it in 15ml of chloroform and dilute it, slowly add it dropwise to the flask in an ice-water bath and stir evenly. After the dropwise addition, move the device to room temperature for 4 hours of reaction. Spot the plate to monitor the progress of the reaction. After the reaction, a brown-red solution was obtained.

[0057] Step 103: After the reaction is finished, filter the filtrate, dilute the filtrate with chloroform, wash with hydrochloric acid aqueous solution to remove excess p...

Embodiment 2

[0059] Aniline dimer derivative C 2 -B 2 preparation of

[0060] Aniline dimer derivative C 2 -B 2 The synthetic route of is as follows:

[0061]

[0062] Specifically include the following steps:

[0063] Step 201: Weigh 1g of N,N'-diphenyl-1,4-p-phenylenediamine and place it in a 100ml three-neck flask, add 3ml of pyridine as an acid-binding agent and 25ml of chloroform as a solvent to fully dissolve, and obtain a solution ;

[0064] Step 202: Measure 6ml of phenylacetyl chloride, dissolve it in 10ml of chloroform and dilute it, slowly drop it into the flask in an ice-water bath and stir evenly. The board monitors the progress of the reaction;

[0065] Step 203: After the reaction is over, filter the filtrate, extract with excess chloroform and hydrochloric acid aqueous solution, and then repeatedly wash with aqueous solution until the pH is about 7 to remove excess pyridine and pyridine hydrochloride; separate the organic layer and add appropriate amount of Wa...

Embodiment 3

[0067] Aniline dimer derivative C 2 -C 2 preparation of

[0068] Aniline dimer derivative C 2 -C 2 The synthetic route of is as follows:

[0069]

[0070] Specifically include the following steps:

[0071] Step 301: Weigh 1g of N,N'-diphenyl-1,4-p-phenylenediamine and place it in a 100ml three-neck flask, add 3ml of pyridine as an acid-binding agent and 25ml of dichloromethane as a solvent to fully dissolve, and obtain a solution ;

[0072] Step 302: Measure 2.6ml of diphenylacetyl chloride, dissolve it in 10ml of dichloromethane and dilute it, slowly add it dropwise to the flask in an ice-water bath and stir evenly, after the drop is completed, move the device to room temperature for 4 hours to react. During the process, the plate is continuously tapped to monitor the reaction process;

[0073] Step 303: After the reaction is completed, filter the filtrate, extract with excess dichloromethane and hydrochloric acid aqueous solution, and then repeatedly wash with a...

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Abstract

The invention belongs to the field of photo-luminescent materials, and relates to a benzoyl-modified aggregation-induced emission type aniline oligomer and a preparation method thereof. According to the method, aniline oligomers with different chain lengths and acyl chloride substituted by groups are used as initial reactants, the chain length of aniline and the variety, number and position of acyl chloride substituent groups are changed to obtain various aniline oligomer derivatives with carbonyl amine structures, and the problem of fluorescence quenching caused by aggregation of aniline oligomers is efficiently solved. Through various structural representations and performance studies, an expected product is successfully obtained, and the synthesized product shows obvious aggregation-induced emission characteristics. Tunable luminescence of aniline oligomer derivatives modified by different benzoyl groups can be realized through control of side groups.

Description

technical field [0001] The invention belongs to the field of photoluminescent materials, in particular to a benzoyl-modified aggregation-induced light-emitting aniline oligomer and a preparation method thereof. Background technique [0002] During the aggregation process of traditional organic light-emitting materials, non-radiative energy transfer occurs due to π-π stacking, which leads to the quenching of self-luminescence to a large extent. Some aromatic compounds with a special "propeller" structure, in the dissolved state, because the rotation of the "propeller" consumes the energy of the excited state molecules, so the fluorescence is very weak, but in the aggregated state due to the distorted molecular conformation, it is difficult for the fluorescent molecules to form better The flatness of π-π stacking is effectively avoided, the non-radiative energy consumption is greatly reduced, and the fluorescence intensity is significantly enhanced, that is, aggregation-induce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/80C07C233/44C09K11/06
CPCC07C231/02C09K11/06C09K2211/1007C09K2211/1014C07C233/80C07C233/44
Inventor 杨继萍刘蓓蓓阿合波塔.巴合提陆浩王萌
Owner BEIHANG UNIV
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