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Viologen compound, and preparation method and application thereof

A technology of compound and alkyl, which is applied in the field of chemical industry and materials, and electrochromic materials, can solve the problems of weak electroactivity, large quality loss in the post-processing process, and high cost.

Inactive Publication Date: 2015-05-13
BEIJING INSTITUTE OF CLOTHING TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The research on viologen compounds mostly focuses on electron transfer sensors, photochromism and electrochromism, but most of the viologen compounds used to study electrochromism in the past are asymmetric viologens, and the synthesis of such viologens is relatively complicated and difficult. The product separation is more complicated, and the quality loss in the post-treatment process is large, which increases the cost (Mei Li.Highly contrasted and stable electrochromic device based on well-matched violence and triphenylamine[J].Organic Electronic,2014,15:428-434)
[0006] There is also the mention of methyl viologen hydrate in the prior art, which is feasible for discoloration reaction on paper, but the discoloration process is slow, and the dimerization is very obvious; Viologen is brown-red and has only weak electrical activity (Paul M.S.Monk, Claire Turner. Electrochemical behavior of methyl viologen in a matrix of Paper[J]. Electrochimica Acta, 1999, 44:4817-4826)

Method used

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  • Viologen compound, and preparation method and application thereof
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  • Viologen compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] Example 1: 1,1'-bis(n-hexadecyl)-4,4'-bipyridinium dibromide (HV) preparation of

[0097]Dissolve 0.0025mol 4,4'-bipyridine in 5mL DMF (N'N dimethylformamide), then add 0.01mol hexadecane bromide solution diluted with 5mL DMF, stir magnetically for 30 minutes, and place Heat the reaction at a constant temperature of 60°C in an oil bath for 72h. Then, excess anhydrous diethyl ether was added to the reacted solution to form a precipitate, filtered by suction, and finally dried in a vacuum oven at 70°C to obtain a yellow powder. The dried powder was recrystallized, and the operation was repeated three times to obtain yellow crystals, that is, 1,1'-bis(n-hexadecyl)-4,4'-bipyridyl dibromide, with a yield of 76%. 1 H NMR (300MHz, MeOD): 0.92(t,6H); 1.25-1.51(m,52H); 2.12(d,4H); 4.78(t,4H); 8.70(d,4H); ).

[0098] The reaction formula is as follows:

[0099]

[0100] Wherein, the steps of recrystallization are as follows:

[0101] Put the dried powder into a 50mL r...

Embodiment 2

[0103] Example 2: 1,1'-bis(n-dodecyl)-4,4'-bipyridylium dibromide (DoV) preparation of

[0104] Dissolve 0.0025mol 4,4'-bipyridine in 5mL DMF, add 0.01mol bromododecane solution diluted with 5mL DMF, stir magnetically for 30 minutes, then place in an oil bath at a constant temperature of 60°C and heat for 72h . Then add excess anhydrous diethyl ether to the reacted solution to form a precipitate, filter it with suction, and finally put it in a vacuum oven at 70°C to dry to obtain a dark yellow powder; dissolve the dried powder into an acetonitrile solution for re- The crystallization operation was performed three times (the specific operation steps of recrystallization are exactly the same as in Example 1), and light yellow crystals were obtained, namely 1,1'-bis(n-dodecyl)-4,4'-bipyridyl dibromide, producing rate of 74%. 1 H NMR (300MHz, MeOD): 0.92(t,6H); 1.25-1.51(m,36H); 2.12(d,4H); 4.75(t,4H); 8.70(d,4H); ).

[0105] The reaction formula is as follows:

[0106] ...

Embodiment 3

[0107] Embodiment 3: Preparation of electrochromic thin film material 1

[0108] Take an appropriate amount of 1,1'-bis(n-hexadecyl)-4,4'-bipyridinium dibromide (HV) prepared in Example 1, and dissolve it in ethanol / water=1 / 1 (volume ratio) In the solvent, the HV solution of 1-10mmol / L is obtained after the dissolution is complete, and an appropriate amount of solution is dropped on the conductive surface of the ITO conductive glass. In order to ensure that the thickness of the prepared film is consistent, the HV solution dropped on the ITO is constant. After uniform scraping, put it into an oven with a temperature of 80°C for rapid drying and prepare it as an HV electrochromic film material coated on ITO conductive glass.

[0109] Thus, the electrochromic thin film material 1 was produced.

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Abstract

The invention relates to the fields of chemical industry and materials, specifically to the field of electrochromic materials, more specifically to a viologen compound, and a preparation method and application thereof. Specifically, the viologen compound is as shown in a formula I which is described in the specification. The invention also relates to a viologen electrochromic material and an electrochromic device. The electrochromic material prepared in the invention has obvious color changes during coloring and fading and has certain cyclic stability and good application prospects.

Description

technical field [0001] The invention belongs to the fields of chemical industry and materials, in particular, relates to the field of electrochromic materials, more specifically, relates to a viologen compound, its preparation method and application. The invention also relates to a viologen electrochromic material and an electrochromic device. Background technique [0002] Electrochromism means that under the action of an applied current or electric field, the optical properties of the material (transmittance, reflectivity, absorptivity and emissivity, etc.) produce stable and reversible changes in the range of visible light wavelengths, and the appearance is expressed as color. and other reversible changes in optical properties. Due to their unique photoelectric properties, electrochromic materials and devices have great application prospects in many fields such as new display devices, information storage devices, adjustable reflectivity automotive rearview mirrors, and sm...

Claims

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Application Information

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IPC IPC(8): C07D213/22C09K9/02G02F1/15
CPCC07D213/22C07D213/127C09K9/02C09K2211/1029G02F1/15
Inventor 李昕袁丽李从举张天骄张德权
Owner BEIJING INSTITUTE OF CLOTHING TECHNOLOGY
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