Viologen derivative electrochromic material and preparation method thereof

A technology of electrochromic materials and derivatives, applied in the direction of color-changing fluorescent materials, chemical instruments and methods, organic chemistry, etc., can solve problems such as liquid electrolyte leakage, and achieve electrolyte leakage, good designability, and high contrast Effect

Active Publication Date: 2020-09-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the electrolyte of the electrochromic device provided by this technology is a liquid electrolyte, and there is a problem of leakage of the liquid electrolyte.

Method used

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  • Viologen derivative electrochromic material and preparation method thereof
  • Viologen derivative electrochromic material and preparation method thereof
  • Viologen derivative electrochromic material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] A preparation method of viologen derivative electrochromic material (A) 1,1'-(4-pyrrolylphenyl)-4,4'-bipyridine, comprising the following steps:

[0057] 1) Add 2.1g of pyrrole, 40mL of DMF, 8.9g of K to a 250mL three-neck flask 2 CO 3 , at 100°C N 2 Stir in the atmosphere for 30min, then add 5.4g of p-fluoronitrobenzene, and heat to reflux for 5h; after the reaction is completed, cool the solution to room temperature, add cold water, precipitate, and filter; wash the precipitate with water for 3 times, and dry; 100mL of diethyl ether was treated to obtain N-(4-nitrophenyl)pyrrole with a yield of 66%;

[0058] MS: m / z=188.1

[0059] 1 H NMR (600MHz, Chloroform-d) δ8.24(d,2H),7.88(d,2H),7.32(d,2H),6.34(t,2H).

[0060] Instruments used: mass spectrometry (MS) liquid chromatography-mass spectrometry, specification Agilent1100, produced by Bruker Company, Germany; hydrogen spectrum (1H NMR) nuclear magnetic resonance spectrometer, specification AVANCE III HD400, produc...

Embodiment 2

[0081] A method for preparing viologen derivative electrochromic material 1,1'-(4-pyrrolylphenyl)-4,4'-bipyridine, comprising the following steps:

[0082] 1) Add 4.2g of pyrrole, 80mL of DMF, 17.9g of K to a 250mL three-necked flask 2 CO 3 , at 100°C N 2 Stir in the atmosphere for 30min, then add 10.8g of p-fluoronitrobenzene, and heat to reflux for 5h; after the reaction is completed, cool the solution to room temperature, add cold water, precipitate, and filter; wash the precipitate with water for 3 times, and dry; 100mL of diethyl ether was treated to obtain N-p-nitrophenylpyrrole with a yield of 68.9%;

[0083] MS: m / z=188.1

[0084] 1 H NMR (600MHz, Chloroform-d) δ8.24(d,2H),7.88(d,2H),7.32(d,2H),6.34(t,2H).

[0085] Instruments used: mass spectrometry (MS) liquid chromatography-mass spectrometry, specification Agilent1100, produced by Bruker, Germany; hydrogen spectrum (1H NMR) nuclear magnetic resonance spectrometer, specification AVANCE III HD400, produced by Bru...

Embodiment 3

[0105] A preparation method of viologen derivative electrochromic material (B) 1,1'-(4-carbazolylphenyl)-4,4'-bipyridine, comprising the steps of:

[0106] 1) Add 4.18g carbazole, 40mL dry DMSO, 5.18g K 2 CO 3 , at N 2 Stir in the atmosphere for 10min, then add 3.6g of p-fluoronitrobenzene, heat up to 110°C, and heat to reflux for 15h; after the reaction is completed, cool the solution to room temperature, add 150mL of methanol to precipitate, and obtain yellow crystal N-p-nitrophenylcarba Azole, yield 75.4%;

[0107] MS: m / z=288.1

[0108] 1 H NMR (600MHz, Chloroform-d) δ8.36(d,2H),8.33(d,2H),8.04(d,2H),7.90(d,2H),7.39(t,2H),7.32(t, 2H).

[0109] Instruments used: mass spectrometry (MS) liquid chromatography-mass spectrometry, specification Agilent1100, produced by Bruker, Germany; hydrogen spectrum (1H NMR) nuclear magnetic resonance spectrometer, specification AVANCE III HD400, produced by Bruker, Germany.

[0110] 2) Add 5.2g of N-p-nitrophenylcarbazole, 0.2g of Pd / ...

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Abstract

The invention discloses a purpurine derivative electrochromic material and a preparation method thereof. The preparation method comprises the steps that 4,4'-dipyridine is adopted as a raw material and undergoes a Menschutkin reaction with 1-chloro-2,4-dinitrobenzene to synthesize a 1,1'-bis(2,4-dinitro)-4,4'-dipyridyl salt; then an N-heterocyclic compound and p-fluoronitrobenzene are subjected toaromatic nucleophilic amination to prepare a 4-nitrocompound, and then the 4-nitrocompound is reduced into a 4-amino compound; finally, the products obtained after the reactions in the two steps undergo a Zincke reaction to obtain a target product. A pyrrole group and carbazole are introduced into a derivative, the electron deficient state of the core group 4,4'-dipyridine of a purpurine compoundis improved, and the electrochromic voltage of the purpurine compound is reduced; moreover,a bipolar electrochromic device can be obtained, a higher contrast ratio is realized, multiple color changesare obtained, and the problem of electrolyte leakage of solution-type electrochromic devices can also be solved.

Description

technical field [0001] The invention relates to an electrochromic material, in particular to a viologen derivative used as an electrochromic material and a preparation method thereof, belonging to the technical field of photoelectric materials. Background technique [0002] Electrochromism refers to the phenomenon of stable and reversible changes between the colored state and the decolorized state of the material by injecting or extracting charges (ions or electrons) under the action of an external electric field. Variety. Since the 21st century, the development and application of electrochromic technology is constantly changing people's lives. Smart anti-glare mirrors for cars make people's driving safer, smart dimming portholes for aircraft make people's travel more comfortable, and smart windows for buildings with dimmable and heat adjustment make people's homes more energy-efficient. Electrochromic technology is an emerging industrial technology, which has huge potenti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C09K9/02G02F1/1516
CPCC07D401/14C09K9/02C09K2211/1007C09K2211/1029G02F1/1516
Inventor 朱咪咪刘平曾金明李辉
Owner SOUTH CHINA UNIV OF TECH
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