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A class of electrochromic materials containing dipyrrolidone acene and its preparation method and application

A dipyrrolidone and color-induced technology, which is applied in the direction of color-changing fluorescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problem of single color, and achieve the effect of simple preparation, low cost and rich colors

Active Publication Date: 2021-02-26
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nowadays, WO 3 It has become one of the most widely researched and industrially applied electrochromic materials, but it has many limitations such as single color

Method used

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  • A class of electrochromic materials containing dipyrrolidone acene and its preparation method and application
  • A class of electrochromic materials containing dipyrrolidone acene and its preparation method and application
  • A class of electrochromic materials containing dipyrrolidone acene and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the synthesis and application of compound 1:

[0044]

[0045] Preparation of Intermediate 1b:

[0046] Under nitrogen protection, 0.2g (0.4mmol) compound a (synthetic method reference H.Zhang, B.Tieke, Polym.Chem.2014,5,6391-6406) and 0.22g (1.6mmol) potassium carbonate were dissolved in 5mL N,N-dimethylformamide, then add 0.22g (1.6mmol) of n-bromobutane, heat to 90°C, and react for 18 hours. After the reaction is complete, pour the reaction system into water and wash with ethyl acetate Ester was extracted, the organic phase was washed three times with water, the solvent was removed after drying, and 141 mg of compound 1b was obtained by column separation and purification, with a yield of 54%.

[0047] Preparation of compound 1:

[0048] Under nitrogen protection, 61mg (0.1mmol) 1b and 44mg (0.3mmol) p-cyanophenylboronic acid were dissolved in 9mL toluene and 9mL tetrahydrofuran, 3mL of saturated potassium carbonate aqueous solution was added, and 2...

Embodiment 2

[0050] Embodiment 2: Synthesis and application of small organic molecule compound 2:

[0051]

[0052] Preparation of Intermediate 2b:

[0053] Under nitrogen protection, 0.3g (0.6mmol) of compound a and 0.27g (2.4mmol) of potassium tert-butoxide were dissolved in 3mL of N,N-dimethylformamide, and then 0.46g (2.4mmol) of 2- Bromooctane was heated to 80°C and reacted for 24 hours. After the reaction was complete, the reaction system was poured into water, extracted with ethyl acetate, and the organic phase was washed with water three times. After drying, the solvent was removed, and 259 mg of compound 2b was obtained by column separation and purification. Rate 60%.

[0054] Preparation of compound 2c:

[0055] Under nitrogen protection, 294mg (0.4mmol) 2b and 37mg (0.3mmol) phenylboronic acid were dissolved in 20mL tetrahydrofuran, and 10mL potassium carbonate aqueous solution (2M) and 35mg (0.03mmol) Pd(PPh 3 ) 4 , heated to 85°C, and reacted for 8 hours. After the reac...

Embodiment 3

[0059] Embodiment 3: Synthesis and application of small organic molecule compound 3:

[0060]

[0061] Preparation of Intermediate 3b

[0062] Under nitrogen protection, dissolve 0.4g (0.8mmol) of compound a and 0.22g (4.0mmol) of potassium hydroxide in 5mL of N,N-dimethylformamide, then add 0.66g (4.0mmol) of n-hexyl bromide alkane, heated to 85°C, and reacted for 20 hours. After the reaction was complete, the reaction system was poured into water, extracted with ethyl acetate, the organic phase was washed with water three times, and the solvent was removed after drying. Column separation and purification gave 345 mg of compound 3b, with a yield of 65 %.

[0063] Preparation of compound 3

[0064] Under nitrogen protection, 199mg (0.3mmol) 3b and 137mg (0.9mmol) p-methoxyphenylboronic acid were dissolved in 25mL tetrahydrofuran, 10mL saturated potassium carbonate aqueous solution was added, and 46mg (0.04mmol) Pd(PPh 3 ) 4 , heated to 88°C, reacted for 6 hours, after t...

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Abstract

The invention belongs to the technical field of organic photoelectric materials, in particular to a class of organic electrochromic materials containing a dipyrroleone-acene structure and a synthesis method and application thereof. The dipyrroleone-acene-based organic electrochromic material in the present invention is a kind of optoelectronic material with dipyrroleone-acene as the core, and their colors can be adjusted by changing the groups connected at both ends, so they are rich and colorful. s color. At the same time, this type of material has a series of redox transition states, so it is a class of electrochromic materials with excellent performance, which can be used to prepare multi-color electrochromic devices. Compared with traditional inorganic non-metallic electrochromic materials, the dipyrrolidone acene-based organic materials in the present invention have the advantages of rich colors, low cost, and diversified processing means.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a class of organic electrochromic materials containing a dipyrroleone-acene structure, a synthesis method thereof and an application in electrochromic devices. Background technique [0002] By applying a current or a voltage difference to a certain chemical substance to trigger its oxidation-reduction reaction, it has different absorption or reflection optical properties in different redox states, and thus the phenomenon of reversible color change is called electrochromism. The term "electrochromic" was first proposed by Platt in 1961. In 1969, Deb demonstrated tungsten trioxide WO 3 The film can undergo reversible discoloration under the action of ultraviolet light or voltage. Nowadays, WO 3 It has become one of the most widely researched and industrially applied electrochromic materials, but it has many limitations such as single color. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C07D519/00C09K9/02G02F1/155G02F1/153
CPCC07D487/04C07D519/00C09K9/02C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092G02F1/153G02F1/155
Inventor 周刚凌苑万皓向春兰
Owner FUDAN UNIV