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Triphenylamine derivative based on modification of imidazole ionic liquid and preparation method and application of triphenylamine derivative

An ionic liquid, triphenylamine technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problem of high cost, and achieve the effect of fast response time and high optical contrast

Active Publication Date: 2019-01-18
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method requires more ionic liquids as electrolyte materials, and considering the price of ionic liquids, the cost is higher

Method used

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  • Triphenylamine derivative based on modification of imidazole ionic liquid and preparation method and application of triphenylamine derivative
  • Triphenylamine derivative based on modification of imidazole ionic liquid and preparation method and application of triphenylamine derivative
  • Triphenylamine derivative based on modification of imidazole ionic liquid and preparation method and application of triphenylamine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Synthesis of 4-(Diphenylamino)benzonitrile

[0045] Under the protection of nitrogen, dissolve sodium hydride (1.496 g, 62.3 mmol) in DMF (40 mL) and stir well until no bubbles are generated. Diphenylamine (5.11g, 30.2mmol) was added to the solution, after the temperature rose to 100-120°C to stabilize, p-fluorobenzonitrile (4.49g, 37.1mmol) was slowly added, and the system refluxed for 12-16h. After the reaction is completed, after the reaction solution is cooled to room temperature, saturated brine and dichloromethane are added for extraction, the organic phase is collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and subjected to column chromatography for separation and purification. Use 300-400 mesh silica gel as the stationary phase, and use the dichloromethane / petroleum ether volume ratio 1:1 mixture as the mobile phase for elution, collect the eluent containing the target compound, distill under reduced pressure to remo...

Embodiment 2

[0046] Example 2 Synthesis of 4-(Diphenylamino)benzoic acid

[0047] The intermediate 4-(diphenylamino)benzonitrile compound (2.2g, 8.15mmol) was dissolved in a mixture of absolute ethanol (40mL) and 25% NaOH solution (40mL), and reacted at 70-90℃ for 12- 16h. After the reaction, after the reaction solution was cooled to room temperature, 3M HCl (75mL) was added for acidification, the solution changed from clear and transparent to yellow flocculent suspension, suction filtered and collected the filter cake, rinsed with deionized water and placed at 60℃ Under vacuum drying for 24 hours, 2.23 g of the yellow powdery intermediate product 4-(diphenylamino)benzoic acid compound was obtained, and the yield was 64.8%. 1 H NMR(500MHz, CDCl 3 ): δ 7.91 (t, 2H), 7.34 (t, 4H), 7.17 (d, 6H), 7.01 (d, 2H); MS (EI): m / z (%): 290.2.

Embodiment 3

[0048] Example 3 Synthesis of 4-(Diphenylamino)benzoate

[0049] The intermediate product 4-(diphenylamino) benzoic acid compound (1g, 3.5mmol), 4-DMAP (0.22g, 1.75mmol), EDCI (2.02g, 10.5mmol), 6-bromo-1-hexanol (0.95 g, 5.25mmol) was dissolved in DCM (25mL) solution and reacted at 20-40℃ for 12-16h. After the reaction is completed, after the reaction solution is cooled to room temperature, saturated brine and dichloromethane are added for extraction, the organic phase is collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and subjected to column chromatography for separation and purification. Use 300-400 mesh silica gel as the stationary phase, and use the dichloromethane / petroleum ether volume ratio 1:1 mixture as the mobile phase for elution, collect the eluent containing the target compound, distill under reduced pressure to remove the solvent and dry to obtain a yellow color The viscous intermediate 4-(diphenylamino)benzoate compound was...

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Abstract

The invention discloses a preparation method of a triphenylamine derivative based on the modification of imidazole ionic liquid represented by a formula (I) (shown in the description) and a method forpreparing a copolymer film represented by a formula (VI) (shown in the description) through EDOT electrochemistry copolymerization. The film prepared through the polymerization of a material synthesized by virtue of the method can be applied to the electrochromic field, is high in response time and is an electrochromic material with excellent performance.

Description

(1) Technical field [0001] The invention relates to a triphenylamine derivative modified by an imidazole-type ionic liquid and a preparation method thereof, as well as to polymerize the material to form a film by an electrochemical copolymerization method, and is used as a novel photoelectric functional material in the fields of electrochromism and the like. (2) Background technology [0002] Since the concept of electrochromic was proposed in 1961, electrochromic materials have become a popular research hotspot. After decades of development, a wide variety of electrochromic materials have emerged. Among them, conjugated polymer electrochromic materials have gradually emerged based on their high coloring efficiency, fast response speed, rich color changes and easy adjustment. It has become a hot spot in the research of electrochromic materials. [0003] Response speed is an important performance measure of electrochromic materials. At present, the response time of PEC materials i...

Claims

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Application Information

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IPC IPC(8): C07D233/58C09K9/02
CPCC07D233/58C08G61/122C08G61/126C08G2261/124C08G2261/143C08G2261/148C08G2261/149C08G2261/3162C08G2261/3242C08G2261/3243C08G2261/44C08G2261/5222C08J5/18C08J2365/00C09K9/02C09K2211/1425C09K2211/1433C09K2211/145C09K2211/1458C09K2211/1466
Inventor 吕晓静钱亮张诚黄从惠朱睿
Owner ZHEJIANG UNIV OF TECH
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