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A kind of aniline oligomer derivative with Schiff base structure and preparation method thereof

An oligomer and Schiff base technology, applied in the field of Schiff base structure aniline oligomer derivatives and their preparation, can solve the problems of color adjustment and limitation of wide application, etc.

Active Publication Date: 2021-05-07
BEIHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the color adjustment problem of aniline oligomer electrochromic materials limits its wider application

Method used

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  • A kind of aniline oligomer derivative with Schiff base structure and preparation method thereof
  • A kind of aniline oligomer derivative with Schiff base structure and preparation method thereof
  • A kind of aniline oligomer derivative with Schiff base structure and preparation method thereof

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preparation example Construction

[0090] The method for preparing the above-mentioned aniline oligomer derivatives with Schiff base structure of the present invention is prepared under normal pressure reflux conditions, and specifically includes the following steps:

[0091] Raw material preparation:

[0092] The aniline oligomer and substituted aromatic formaldehyde are prepared as raw materials according to the molar ratio of 1:1.05, and the catalyst camphorsulfonic acid is prepared according to 1 to 3% of the total mass of the two reactants;

[0093] Reaction conditions:

[0094] Reaction step 1-1: Disperse aniline oligomer, substituted aromatic formaldehyde, and camphorsulfonic acid in tetrahydrofuran at an ambient temperature of 80°C, the total concentration of the above solids is 5 mg / ml, and the stirring speed is 20-40 rpm to obtain mixture;

[0095] Reaction step 1-2: reacting the mixture at an ambient temperature of 80°C and a stirring speed of 20-40 rpm for 6-8 hours;

[0096] Reaction step 1-3: r...

Embodiment 1

[0101] Add 0.128g 2-hydroxybenzaldehyde, 0.366g aniline tetramer, 0.01g (2wt%) camphorsulfonic acid and 100ml tetrahydrofuran into a 250ml flask, stir at 20-40 rpm, and react for 6-8 minutes at 80°C. Hour. The solvent tetrahydrofuran was removed from the reacted mixture with a rotary evaporator to obtain a solid crude product. The obtained crude product was then fully dissolved in ethyl acetate, and insoluble components were filtered off. Pour the concentrated filtrate into a large amount of petroleum ether for precipitation. Using ethyl acetate and petroleum ether as eluents, the precipitate was purified by thin-layer chromatography (TLC), and then the precipitate was vacuum-dried at 45°C for 24 hours to obtain an aniline oligomer derivative with Schiff base structure TANI-2OH-BA, its structural formula is:

[0102]

[0103] Carry out infrared spectrum analysis to raw material aniline tetramer, such as figure 1 As shown in the picture, 1602cm -1 and 1514cm -1 Nearby ...

Embodiment 2

[0106]In a 250ml flask, add 0.203g 4-(diethylamino) salicylaldehyde, 0.366g aniline tetramer, 0.01g (2wt%) camphorsulfonic acid and 100ml tetrahydrofuran, stirring speed is 20~40 rev / min, 80 ℃ Under the reaction for 6 to 8 hours. The solvent tetrahydrofuran was removed from the reacted mixture with a rotary evaporator to obtain a solid crude product. The obtained crude product was then fully dissolved in ethyl acetate, and insoluble components were filtered off. Pour the concentrated filtrate into a large amount of petroleum ether for precipitation. Using ethyl acetate and petroleum ether as eluents, the precipitate was purified by thin-layer chromatography (TLC), and then the precipitate was vacuum-dried at 45°C for 24 hours to obtain an aniline oligomer derivative with Schiff base structure TANI-4DEA-2OH-BA, the structural formula is:

[0107]

[0108] Carry out infrared spectrum analysis to the TANI-4DEA-2OH-BA Schiff base structure aniline oligomer derivative that em...

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Abstract

The invention belongs to the field of organic electrochromic materials, and in particular relates to a derivative of aniline oligomer with Schiff base structure and a preparation method thereof. According to the type of the ring and the type, number, and position of the substituent group, a variety of aniline oligomer derivatives with a Schiff base structure can be obtained, which solves the color adjustment problem of the aniline oligomer electrochromic material. After various tests and characterizations, the invention successfully obtains the target product and can realize the color adjustment of the aniline oligomer.

Description

technical field [0001] The invention belongs to the field of organic electrochromic materials, in particular to a class of aniline oligomer derivatives with a Schiff base structure and a preparation method thereof. A series of aniline oligomer derivatives with Schiff base structure prepared by the invention have different color changes from aniline oligomers, and can be used as electrochromic materials. Background technique [0002] Electrochromic materials have the property of exhibiting reversible color changes under different electric potentials. Color tuning plays a key role in applications such as camouflage and electrochromic displays. In camouflage, electrochromic materials need to show colors that are close to natural colors, such as khaki, grass green, lake blue, etc. However, in electrochromic display, the requirements of three primary colors need to be met. [0003] Organic electrochromic materials are often used in color design due to their rich color changes ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/24C07C249/02
CPCC07C251/24
Inventor 杨继萍王萌陆浩刘蓓蓓
Owner BEIHANG UNIV
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