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Preparation of novel viologen electrochromic material and application thereof

An electrochromic material and electrochromic technology, applied in the direction of color-changing fluorescent materials, instruments, organic chemistry, etc., can solve the problems of reducing electrochromic voltage, complex synthesis process, single color type, etc., and achieve low color-changing voltage. Good stability and wide range of discoloration

Inactive Publication Date: 2019-12-31
INST OF PROCESS ENG CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention provides a novel viologen electrochromic material in order to overcome the disadvantages of complex synthesis process, high color-changing voltage, small transmittance difference, single color type, and electrolyte leakage of solution-type electrochromic devices in the prior art. The viologen electrochromic compound introduces an aromatic group, which improves the electron-deficient state on the core group 4,4'-bipyridine of the viologen compound, reduces its electrochromic voltage, and has a higher transmittance difference and discoloration. Faster and longer service life, the electrochromic device prepared by using it has outstanding color-changing performance and cost advantages

Method used

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  • Preparation of novel viologen electrochromic material and application thereof
  • Preparation of novel viologen electrochromic material and application thereof
  • Preparation of novel viologen electrochromic material and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0035] The present embodiment provides a kind of viologen electrochromic material formula (1), and its preparation method comprises the following steps:

[0036] (1) Dissolve 1.825g of 4,4-bipyridine in 10ml of ACN, slowly drop into it 2g of 1-bromoheptane solution diluted with 10ml of ACN, stir and react at 50°C for 72h, filter and wash with anhydrous ether, After vacuum drying at 50°C for 24 hours, 1-heptyl-4,4'-bipyridyl bromide (MHVBr) was obtained with a yield of 47%.

[0037] (2) 1.675 g of the solid product obtained in step (1) was dissolved in 10 ml of DMF, and 1.53 g of p-chloromethylstyrene solution diluted with 5 ml of DMF was slowly added dropwise thereto, and the reaction was stirred at 60° C. for 72 h, Filter and wash with anhydrous ether, and dry in vacuum at 50°C for 24 hours to obtain 1-heptyl-1-[4'-(vinyl)benzyl]-4,4'-bipyridyl chloride bromide (HBVBrCl), product The rate is 60%.

[0038] (3) Dissolve 0.5 g of 1-heptyl-1-[4-(vinyl)benzyl]-4,4'-bipyridyl chl...

Embodiment 2

[0043] The present embodiment provides a kind of viologen electrochromic material formula (2), and its preparation method comprises the following steps:

[0044] (1) Dissolve 1.825g of 4,4-bipyridine in 10ml of ACN, slowly drop into it 2g of 1-bromoheptane solution diluted with 10ml of ACN, stir and react at 50°C for 72h, filter and wash with anhydrous ether , dried under vacuum at 50°C for 24 hours to obtain 1-heptyl-4,4'-bipyridyl bromide with a yield of 47%.

[0045] (2) Dissolve 0.9 g of the solid product obtained in step (1) in 10 ml of DMF, slowly drop into it 0.33 g of 1,6-dibromohexane solution diluted with 5 ml of DMF, and stir the reaction at 60° C. for 72 h, Filter and wash with anhydrous ether, and dry at 50°C for 24 hours to obtain 1-heptyl-1-[1-hexyl-1-heptyl-4,4'-bipyridyl]-4,4'-bipyridyl tetrabromide , the yield was 36%.

[0046] (3) 0.3g of 1-heptyl-1-[1-hexyl-1-heptyl-4,4'-bipyridyl]-4,4'-bipyridyl tetrabromide prepared in step (2) Dissolve in 5ml deionize...

Embodiment 3

[0051] The present embodiment provides a kind of viologen electrochromic material formula (3), and its preparation method comprises the following steps:

[0052] (1) Dissolve 1.825g of 4,4-bipyridine in 10ml of ACN, slowly drop into it 2g of 1-bromoheptane solution diluted with 10ml of ACN, stir and react at 50°C for 72h, filter and wash with anhydrous ether, After vacuum drying at 50°C for 24 hours, 1-heptyl-4,4'-bipyridyl bromide (MHVBr) was obtained with a yield of 47%.

[0053] (2) 1.675 g of the solid product obtained in step (1) was dissolved in 10 ml of DMF, and 1.53 g of p-chloromethylstyrene solution diluted with 5 ml of DMF was slowly added dropwise thereto, and the reaction was stirred at 60° C. for 72 h, Filter and wash with anhydrous ether, and dry in vacuum at 50°C for 24 hours to obtain 1-heptyl-1-[4'-(vinyl)benzyl]-4,4'-bipyridyl chloride bromide (HBVBrCl), product The rate is 60%.

[0054] (3) Dissolve 1 g of 1-heptyl-1-[4-(vinyl)benzyl]-4,4'-bipyridyl chlor...

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Abstract

The invention relates to a preparation and application of a novel viologen electrochromic material. The preparation method comprises the steps of taking 4,4'-bipyridyl as a raw material, and performing Menschutkin reaction with halogenated alkane to synthesize monosubstituted 4,4'-bipyridyl salt; then, importing aromatic groups into the monosubstituted 4,4'-bipyridyl salt to increase a conjugatedstructure of molecules, and then increasing the stability of the molecules and improving the radiation resistance and temperature resistance of molecular chains. In addition, along with the growth ofmolecular chains and the importing of the aromatic groups, the electron-deficient state on 4,4'-bipyridyl of the core group of the viologen compound is improved, a proper substituent is selected, different colors can be obtained by adjusting the molecular orbital energy level and the charge transfer capacity, and the possibility is provided for realizing multicolor display. The viologen electrochromic material obtained by the invention is higher in transmittance difference, quicker in color change, lower in color change voltage and longer in service life, and the electrochromic device preparedby using the viologen electrochromic material has outstanding color change performance and cost advantage.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to the preparation and application of a novel viologen electrochromic material. Background technique [0002] Electrochromism refers to the phenomenon that the optical properties (transmittance or reflectance) of materials produce stable and reversible changes in the range of visible light under the action of an external electric field. In appearance, it shows reversible changes in color and transparency. Materials with electrochromic capabilities are called electrochromic materials, and devices made using electrochromic materials are called electrochromic devices. The performance of the electrochromic device is closely related to the performance of the electrochromic material. Selecting the appropriate electrochromic material makes the obtained electrochromic device have the advantages of rich color change, large color change range and low driving voltag...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K9/02C07D213/22C08F112/14G02F1/1503G02F1/1516
CPCC07D213/22C08F112/14C09K9/02C09K2211/1029C09K2211/1466G02F1/1503G02F1/1516G02F1/15165
Inventor 张锁江赵炜珍王秀秀
Owner INST OF PROCESS ENG CHINESE ACAD OF SCI
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