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A kind of bistable electrochromic fluorane dye and preparation method thereof

An electrochromic device and fluoran dye technology, applied in the field of material science, can solve the problem that the color development state can only be maintained for a few minutes, and achieve the effect of improving the electrochromic response rate and excellent bistable characteristics.

Active Publication Date: 2022-08-02
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Compared with other color-changing materials, fluorane-based leuco dyes have attracted extensive attention due to their advantages such as high molar absorption coefficient, low driving voltage, bright and rich colors, and multiple responses to cycles. However, in the prior art, based on fluorane Dye-like electrochromic display devices can only maintain the color state for a few minutes after the voltage is removed

Method used

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  • A kind of bistable electrochromic fluorane dye and preparation method thereof
  • A kind of bistable electrochromic fluorane dye and preparation method thereof
  • A kind of bistable electrochromic fluorane dye and preparation method thereof

Examples

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Effect test

Embodiment 1

[0042] Preparation of red No. 3 novel fluoran dye: 50mmol 3-(diethylamino)phenol and 25mmol 3-nitrophthalic anhydride were added to a three-necked flask containing 50mL of chlorobenzene, after complete dissolution, 25mmol of trifluoride was added Methanesulfonic acid. Then, the three-necked flask was placed in a 135° C. oil bath to preheat, and the reaction was carried out under nitrogen reflux for 2 days. After the reaction was completed, it was cooled to room temperature, and the solvent was removed by rotary evaporation. Column chromatography was carried out with dichloromethane (DCM) / methanol as the eluent to obtain a purple-red powder, namely the product ph-NO 2 .

[0043] 1mmol ph-NO 2 , 20 mg of Pd / C, 4 mL of ethyl acetate (EtOAc) were placed in a three-necked flask. 1.5mmol H 3 PO 2 and 4.5mmol NaH 2 PO 2 ·H 2 O is homogeneously dissolved in 4 mL of H 2 After O, poured into the above three-necked flask. Then, the three-necked flask was placed in an oil bath a...

Embodiment 2

[0064] Preparation of red No. 4 novel fluoran dye: 50mmol of 3-(diethylamino)phenol and 25mmol of 3-nitrophthalic anhydride were added to a three-necked flask containing 50mL of chlorobenzene, and after completely dissolving, 25mmol of trifluoride was added Methanesulfonic acid. Then, the three-necked flask was placed in a 135° C. oil bath to preheat, and the reaction was carried out under nitrogen reflux for 2 days. After the reaction was completed, it was cooled to room temperature, and the solvent was removed by rotary evaporation. Column chromatography was carried out with dichloromethane (DCM) / methanol as the eluent to obtain a purple-red powder, namely the product ph-NO 2 .

[0065] 1mmol ph-NO 2 , 20 mg of Pd / C, 4 mL of ethyl acetate (EtOAc) were placed in a three-necked flask. 1.5mmol H 3 PO 2 and 4.5mmol NaH 2 PO 2 ·H 2 O is homogeneously dissolved in 4 mL of H 2 After O, poured into the above three-necked flask. Then, the three-necked flask was placed in an...

Embodiment 3

[0074] Preparation of Green No. 3 Novel Fluoran Dye: Dissolve 3-diethylaminophenol (1.65g) and 3-nitrophthalic anhydride (2.89g) in toluene (25ml), put into a three-necked The reaction was carried out in a bath for 4 h, cooled to room temperature, and extracted with a small amount of petroleum ether. The supernatant was removed to obtain a purple-red precipitate. The precipitate was purified by column chromatography using dichloromethane / methanol as the eluent to obtain a golden yellow powder, which was the product 4-diethylaminonitroketo acid.

[0075] 4-Diethylamino nitroketo acid (intermediate M1) (2 g) and concentrated sulfuric acid (15 ml) were put into a three-necked flask, and the powder was dissolved in an ice-water bath. Then 4-methoxydiphenylamine (1.11 g) was put into the above three-necked flask, and the reaction was carried out at room temperature for 24 h. After that, the product was slowly dropped into ice water to obtain a dark green precipitate, which was wa...

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Abstract

The invention belongs to the technical field of material science, and in particular relates to a preparation method of a bistable electrochromic fluorane dye and a device thereof. The invention designs and synthesizes a series of novel fluoran dyes which have bistable performance, bright and rich colors, fast switching rate and the like, and prepare bistable by adding polymethyl methacrylate, propylene carbonate and electrolyte. state electrochromic displays. The electrochromic device obtained based on the novel fluoran dye of the present invention has excellent bistable characteristics, which is embodied as follows: after removing the voltage stimulus, the color development state can still be maintained for more than a week. By adjusting the structure of the novel fluoran dye, red, yellow, green, blue, black and other colorful bistable electrochromic devices can be prepared.

Description

technical field [0001] The invention belongs to the technical field of material science, and particularly relates to a preparation method of a bistable electrochromic fluorane dye and a device thereof. Background technique [0002] Bistable electrochromic materials have attracted more and more attention because they can continuously output pattern signals such as color and text for a long time without consuming electrical energy. Bistable electrochromic materials have been used in products such as smart windows, e-book readers, soft robots, electronic shelf labels, and smart color-changing fiber fabrics. [0003] Many inorganic and organic materials are ideal raw materials for the production of bistable electrochromic devices. Among them, inorganic materials usually achieve discoloration based on the redox reaction between two metals, and achieve bistable performance by stabilizing the oxidized and reduced states. It has been reported that a bistable electrochromic dynamic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10C09B57/00C09K9/02G02F1/1516
CPCC07D493/10C09B57/00C09K9/02G02F1/1516C09K2211/1014C09K2211/1088
Inventor 张丽平付少海王成成李加双
Owner JIANGNAN UNIV
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