Bistable electrochromic fluorane dye and preparation method of bistable electrochromic fluorane dye device

A technology of electrochromic devices and fluorane dyes, which is applied in the field of material science, can solve the problem that the color state can only be maintained for a few minutes, and achieve the effect of improving the response rate of electrochromism and excellent bistable characteristics

Active Publication Date: 2021-09-21
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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  • Bistable electrochromic fluorane dye and preparation method of bistable electrochromic fluorane dye device
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  • Bistable electrochromic fluorane dye and preparation method of bistable electrochromic fluorane dye device

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Embodiment 1

[0042] Preparation of red No. 3 new fluoran dye: 50mmol 3-(diethylamino)phenol and 25mmol 3-nitrophthalic anhydride were added to a three-necked flask containing 50mL chlorobenzene, after they were completely dissolved, 25mmol trifluoro Methanesulfonic acid. Then put the three-neck flask into a 135°C oil bath to preheat, and react under nitrogen reflux for 2 days. After the reaction is completed, cool to room temperature, and remove the solvent by rotary evaporation. Using dichloromethane (DCM) / methanol as eluent for column chromatography, a purple powder was obtained, the product ph-NO 2 .

[0043] 1 mmol ph-NO 2 , 20mg Pd / C, 4mL ethyl acetate (EtOAc), put into a three-necked flask. 1.5 mmol H 3 PO 2 and 4.5 mmol NaH 2 PO 2 ·H 2 O was homogeneously dissolved in 4 mL of H 2 After being in O, it was poured into the above-mentioned three-neck flask. Then the three-neck flask was put into an oil bath at 85°C for 5 hours, cooled to room temperature, and extracted with di...

Embodiment 2

[0064] Preparation of red No. 4 novel fluoran dye: 50mmol 3-(diethylamino)phenol and 25mmol 3-nitrophthalic anhydride were added to a three-necked flask containing 50mL chlorobenzene, after they were completely dissolved, 25mmol trifluoro Methanesulfonic acid. Then put the three-neck flask into a 135°C oil bath to preheat, and react under nitrogen reflux for 2 days. After the reaction is completed, cool to room temperature, and remove the solvent by rotary evaporation. Using dichloromethane (DCM) / methanol as eluent for column chromatography, a purple powder was obtained, the product ph-NO 2 .

[0065] 1 mmol ph-NO 2 , 20mg Pd / C, 4mL ethyl acetate (EtOAc), put into a three-necked flask. 1.5 mmol H 3 PO 2 and 4.5 mmol NaH 2 PO 2 ·H 2 O was homogeneously dissolved in 4 mL of H 2 After being placed in O, it was poured into the above-mentioned three-neck flask. Then the three-neck flask was put into an oil bath at 85°C for 5 hours, cooled to room temperature, and extracte...

Embodiment 3

[0074] Preparation of Green No. 3 novel fluoran dye: 3-diethylaminophenol (1.65g) and 3-nitrophthalic anhydride (2.89g) were dissolved in toluene (25ml), put into a three-necked flask, 110°C oil The reaction was carried out in a bath for 4h, and after cooling to room temperature, it was extracted with a small amount of petroleum ether. The supernatant was removed to obtain a purple-red precipitate. Purify the precipitate by column chromatography using dichloromethane / methanol as the eluent to obtain a golden yellow powder, which is the product 4-diethylaminonitroketoacid.

[0075] Put 4-diethylaminonitroketo acid (intermediate M1) (2g) and concentrated sulfuric acid (15ml) into a three-neck flask, and dissolve the powder in an ice-water bath. Then, 4-methoxydiphenylamine (1.11 g) was put into the above-mentioned three-necked flask, and reacted at room temperature for 24 h. Afterwards, the product was slowly dropped into ice water to obtain a dark green precipitate, which was...

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Abstract

The invention belongs to the technical field of material science, and relates to a bistable electrochromic fluorane dye and a preparation method of a bistable electrochromic fluorane dye device. A series of novel fluorane dyes which have bistable performance and have the characteristics of bright and rich colors, high switching speed and the like are designed and synthesized, and a bistable electrochromic display is prepared by adding polymethyl methacrylate, propylene carbonate and electrolyte. The electrochromic device obtained on the basis of the novel fluorane dyes has excellent bistable characteristics, and specifically, after voltage stimulation is removed, the electrochromic device can still keep the color development state for more than one week. By adjusting the structure of the novel fluorane dyes, colorful bistable electrochromic devices such as red, yellow, green, blue and black bistable electrochromic devices can be prepared.

Description

technical field [0001] The invention belongs to the technical field of material science, and in particular relates to a bistable electrochromic fluoran dye and a preparation method of a device thereof. Background technique [0002] Bistable electrochromic materials are attracting more and more attention because they can continuously output color, text and other pattern signals for a long period of time without consuming electric 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 fabrics. [0003] Many inorganic and organic materials are ideal raw materials for the production of bistable electrochromic devices. Among them, inorganic materials usually realize color change based on the redox reaction between two metals, and achieve bistable performance by stabilizing the oxidation state and reduction state. It has been reported that based on the oxidation-re...

Claims

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Application Information

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Patent Type & Authority Applications(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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