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Thermal crosslinking functionalized triphenylamine polymer as well as preparation method and application thereof

A functionalized, thermal cross-linking technology, applied in the preparation of organic compounds, preparation of aminohydroxy compounds, chemical instruments and methods, etc., can solve the lack of purification and solubility, the limitation of colorless and transparent state, film-forming and stability problems such as poor performance, to achieve the effect of short response time, fast response rate and high transmittance

Active Publication Date: 2020-05-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Small molecules and discrete oligomers have excellent photophysical and electrochromic properties, and can be selected through synthetically tuning their structure and properties, but their film formation and stability are poor
Compared with small organic molecules, polymers can form very stable thin films with better stability, but challenges in purification and solubility and lack of a colorless transparent state limit their wide application

Method used

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  • Thermal crosslinking functionalized triphenylamine polymer as well as preparation method and application thereof
  • Thermal crosslinking functionalized triphenylamine polymer as well as preparation method and application thereof
  • Thermal crosslinking functionalized triphenylamine polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 Synthesis of 1-bromo-4-(4-vinylbenzyloxy)benzene

[0043] 4-vinylbenzyl chloride (2.2g, 14.5mmol), 4-bromophenol (2g, 14.5mmol), K 2 CO 3 (3g, 23.4mmol), 18-crown-6-ether (0.78g, 3mmol) and tetrabutylammonium iodide (0.27g, 0.8mmol) were added in 30mL of anhydrous acetone, and heated to reflux for 16h, the reaction was completed Finally, the reaction solution A was obtained. After the reaction, the reaction solution was cooled to room temperature and quenched by adding water. After that, saturated brine and dichloromethane were added for extraction, and the organic phase was collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography. Use 300-400 mesh silica gel as the stationary phase, elute with dichloromethane / petroleum ether mixed solution with a volume ratio of 1:1 as the mobile phase, collect the eluate containing the target compound, distill off the solvent under reduced p...

Embodiment 2

[0044] Example 2 Synthesis of 4-methoxy-N-(4-(4-vinylbenzyloxy)phenylaniline

[0045] 1-Bromo-4-(4-vinylbenzyloxy)benzene (2g, 6.92mmol), p-anisidine (1.92g, 10.41mmol), KO t Bu(2.33g, 20.83mmol), Pd(OAc) 2 (0.233g, 0.67mmol), which was taken into a 100ml two-necked flask equipped with a septum. 30 mL of anhydrous toluene and tri-tert-butylphosphine (0.631 g, 2.08 mmol) were added, and the reaction mixture was refluxed under nitrogen atmosphere for 24 hours. After the reaction solution was cooled to room temperature, water was added to quench it. After that, saturated brine and dichloromethane were added for extraction, and the organic phase was collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography. Using 300-400 mesh silica gel as the stationary phase, eluting with a dichloromethane / petroleum ether mixture with a volume ratio of 2:1 as the mobile phase, collecting the eluate containing th...

Embodiment 3

[0046] The synthesis of embodiment 3MeO-TPDSt

[0047] Dibromobiphenyl (1.43g, 3.02mmol), product (Ⅲ) 4-methoxy-N-(4-(4-vinylbenzyloxy)phenylaniline (2g, 6.04mmol), KO t Bu(1.36g, 12.08mmol), Pd(OAc) 2 (0.233g, 0.67mmol) and P(t-Bu) 3 (0.631g, 2.08mmol) was added into a two-necked flask containing 30mL of anhydrous toluene at room temperature. The reaction mixture was refluxed for 24 hours under nitrogen atmosphere. After the reaction, the reaction solution was cooled to room temperature, and quenched by adding water. After that, saturated brine and dichloromethane were added for extraction, and the organic phase was collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography. Use 300-400 mesh silica gel as the stationary phase, and use dichloromethane / petroleum ether mixed solution with a volume ratio of 1:1 as the mobile phase for elution, collect the eluate containing the target compound, di...

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Abstract

The invention relates to a thermal crosslinking functionalized triphenylamine polymer as well as a preparation method and application thereof. The structure of the polymer is shown as a formula (I), the polymer is characterized in that two styrene groups are introduced into a triphenylamine derivative, a stable cross-linked polymer film is formed on the surface of an electrode through a thermal polymerization reaction, and the preparation method has the characteristics of low polymerization temperature and short reaction time. The polymer film prepared by the invention can realize transparent-orange-blue reversible color change under different voltages, has the advantages of high optical contrast, high response speed, good cycling stability and the like, and can be used as a novel electrochromic material to be applied to the fields of intelligent windows, rearview mirrors, intelligent glasses and the like.

Description

technical field [0001] The invention relates to a heat-crosslinked functionalized triphenylamine polymer, a preparation method thereof, and its application as a novel electrochromic material. Background technique [0002] Electrochromism refers to the phenomenon that under the action of an applied electric field, the optical properties (such as transmittance, reflectivity or absorptivity) of materials in the ultraviolet-visible or near-infrared region produce stable and reversible changes, and the appearance is manifested as color and transparency. reversible changes. Electrochromic materials and their devices have shown great application prospects in the fields of building energy-saving glass, automobile anti-glare rearview mirror, dimming glass for automobiles or aircraft, and static displays. By applying electrochromic materials to windows to control the light and heat entering the building, it can keep cool in summer and keep warm in winter, and at the same time improve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F112/34C07C213/08C07C217/92C09K9/02
CPCC08F112/34C07C213/08C09K9/02C09K2211/1425C09K2211/1433C07C217/92
Inventor 张诚徐丽斌吕晓静杨园园
Owner ZHEJIANG UNIV OF TECH
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