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Conjugated expanded viologen derivative as well as preparation method and application thereof

A derivative, viologen technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of limited application range, difficulty in making electrochromic devices, monotonous display colors, etc., and achieve low cost and good performance. Electrochromic performance, convenient post-processing effect

Inactive Publication Date: 2013-02-27
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the display color of inorganic electrochromic materials is too monotonous, it is difficult to make full-color electrochromic devices, and the application range is limited to a certain extent.

Method used

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  • Conjugated expanded viologen derivative as well as preparation method and application thereof
  • Conjugated expanded viologen derivative as well as preparation method and application thereof
  • Conjugated expanded viologen derivative as well as preparation method and application thereof

Examples

Experimental program
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Effect test

preparation Embodiment 1

[0028]

[0029] Add 18.2g (0.1mol) of 1,2-bis(4-pyridyl)ethylene into 150ml of acetonitrile, then slowly drop into 35.5g (0.25mol) of methyl iodide, stir at 30°C for 72h, add twice the volume of diethyl ether As a precipitating agent, filter, wash the filter cake with anhydrous ether, and dry at 50°C to obtain N,N'-dimethyl-1,2-bis(4-pyridyl)ethylene bis-quaternary ammonium iodide 1( Orange-red solid), the yield is 82%; the structure of the product is identified to be completely consistent with the above structural formula 1.

preparation Embodiment 2

[0031]

[0032] Add 18.2g (0.1mol) of 1,2-bis(4-pyridyl)ethylene into 150ml of acetonitrile, then slowly drop in 27.2g (0.225mol) of allyl bromide, raise the temperature to 50°C and stir for 72h, then cool to At room temperature, add twice the volume of diethyl ether as a precipitant, filter, wash the filter cake with anhydrous diethyl ether, and dry at 50°C to obtain N,N'-diallyl-1,2-bis(4-pyridyl) Ethylene bis-quaternary ammonium bromide 2 (light yellow solid), the yield is 83%; the structure of the product is identified to be completely consistent with the above structural formula 2.

preparation Embodiment 3

[0034]

[0035] Add 18.2g (0.1mol) of 1,2-bis(4-pyridyl)ethylene into 150ml of acetonitrile, then slowly drop into 33.6g (0.225mol) of bromoisoamylene, heat up to 80°C and reflux for 60h, then cool to At room temperature, add twice the volume of diethyl ether as a precipitant, filter, wash the filter cake with anhydrous diethyl ether, and dry at 50°C to obtain N,N'-diprenyl-1,2-bis(4-pyridyl ) Ethylene bisquaternary ammonium bromide 3 (light yellow solid), the yield is 85%; the structure of the product is identified to be completely consistent with the above structural formula 3.

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Abstract

The invention discloses a conjugated expanded viologen derivative shown in a formula I, wherein X1 and X2 are any one of Cl, Br or I, and R1 and R2 are any one of a fat chain alkyl group or a mono aromatic group; and the conjugated expanded viologen derivative is prepared by reacting 1,2-bi(4-pyridyl)ethylene with halohydrocarbon in an organic solvent at a constant temperature of 30-80 DEG C during stirring. The conjugated expanded viologen derivative is similar to viologen, is an excellent cathode electrochromic material, has favorable electrochromism performance, and especially can display rare red, thereby expanding the color selection range of the electrochromic material, providing a novel red electrochromic display material for the colorful electrochromic material field, and having potential and extensive application prospect in the electrochromic field.

Description

technical field [0001] The invention belongs to the field of preparation of functional materials, and relates to a preparation method of a class of conjugated extended viologen derivatives (mainly vinyl bipyridine quaternary ammonium salt compounds and derivatives thereof), and the use of such derivatives as novel electrochromic materials Applications. Background technique [0002] Electrochromism refers to the phenomenon that the optical properties of materials (reflectivity, transmittance, absorptivity, etc.) undergo stable and reversible changes under the action of an external electric field, and the appearance is manifested as reversible changes in color and transparency. Materials with electrochromic properties are called electrochromic materials. Electrochromic devices made of electrochromic materials have some unique characteristics, such as continuously adjustable optical properties of materials in a wide range, light modulation, low operating voltage, low energy co...

Claims

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Application Information

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IPC IPC(8): C07D213/06C07D213/127C09K9/02
Inventor 傅相锴邓君余建超何俊岭秦主源
Owner SOUTHWEST UNIVERSITY
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