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Four-membered ring pyridine multi-color electrochromic material based on different substituent groups

A cyclopyridine and multi-color technology, which is applied in the direction of color-changing fluorescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of long response time and single color change, and achieve convenient post-processing, broad application prospects, and expanded color selection range effect

Inactive Publication Date: 2017-06-13
SOUTHWEST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a multi-color electrochromic material based on four-membered ring pyridines with different substituents, aiming to solve the problem of long response time and single color change of viologen organic compounds

Method used

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  • Four-membered ring pyridine multi-color electrochromic material based on different substituent groups
  • Four-membered ring pyridine multi-color electrochromic material based on different substituent groups
  • Four-membered ring pyridine multi-color electrochromic material based on different substituent groups

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preparation example Construction

[0035] Such as figure 1 As shown, the preparation method of the multi-color changing four-membered ring pyridine derivative provided by the embodiment of the present invention comprises the following steps:

[0036] S101: Add 1,2,3,4-tetra-(4-pyridine)cyclobutane represented by formula II to the organic solvent, and then dropwise add halogenated hydrocarbon represented by formula III, 1,2,3,4-tetra The mol ratio of -(4-pyridine) cyclobutane to halogenated hydrocarbon is 1:4-4.5;

[0037] S102: Then stir the reaction at a constant temperature of 80-90°C. After the reaction is completed, cool to room temperature, add three times the volume of diethyl ether as a precipitant, filter, and dry the filter cake to obtain 1,2,3,4-tetra-( 4-pyridine) cyclobutane tetrapyridinium salt, ie R 1 , R 2 , R 3 and R 4 same and X 1 、X 2 、X 3 and x 4 the same compound of formula I.

[0038] The chemical reaction formula of the preparation method of the four-membered ring pyridine deriva...

preparation Embodiment 1

[0043]

[0044] Add 0.3g (0.82mmol) of 1,2,3,4-tetra-(4-pyridine) cyclobutane into 8ml of dimethylformamide, then slowly drop into 2ml of iodomethane dissolved in 0.58g (4.1mmol) Dimethylformamide, stirred at 80°C for 36 hours, added three times the volume of ether as a precipitant, filtered, washed the filter cake with anhydrous ether, and dried at 60°C to obtain N,N',N",N" '-Tetramethyl-1,2,3,4-tetrakis(4-pyridyl)cyclobutane quaternary ammonium iodide 1 (yellow black solid), yield 86.0%; 1 HNMR (600MHz, DMSO-d 6 ), δ (ppm): 9.02 (d, 8H, J = 6.60Hz), 8.23 ​​(d, 8H, J = 6.60Hz), 4.67 (s, 4H), 4.34 (s, 12H); 13 CNMR (150MHz, DMSO-d 6 ): 156.28, 145.99, 127.19, 48.05, 48.02. The structure of the product is completely consistent with the above structural formula 1 as determined by NMR.

preparation Embodiment 2

[0046]

[0047] Add 0.3g (0.82mmol) of 1,2,3,4-tetra-(4-pyridine) cyclobutane into 8ml of dimethylformamide, then slowly drop into 2ml of 0.79g (4.1mmol) of n-bromo Dimethylformamide of octane, stirred at 80°C for 36 hours, added three times the volume of diethyl ether as a precipitant, filtered, washed the filter cake with anhydrous ether, and dried at 60°C to obtain N,N',N” ,N"'-tetra-n-octyl-1,2,3,4-tetra(4-pyridyl)cyclobutane pyridinium bromide 2 (light brown solid), yield 56.1%; 1 HNMR (600MHz, DMSO-d 6 )δ (ppm) 9.15 (8H, d, J = 66.0), 8.36 (8H, d, J = 66.0), 4.78 (4H, s), 4.59 (8H, t, J = 15), 1.89 (8H, m ,J=6.0),1.24-1.29(40H,m,J=30.6),0.85(12H,t,J=15.2); 13 CNMR (150MHz, DMSO-d 6 ) 156.87, 145.08, 127.71, 60.76, 47.99, 34.85, 31.58, 28.88, 25.93, 22.46, 14.36.

[0048] The structure of the product is completely consistent with the above structural formula 2 as determined by NMR.

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Abstract

The invention discloses a four-membered ring pyridine multi-color electrochromic material based on different substituent groups. 1,2,3,4-4-(4-pyridine) cyclobutane is synthesized by 1,2-bis(4-pyridine) ethylene as a raw material, and a series of N-substituted salts are synthesized through N-alkylation reaction; the structures of different substituent compound salts are detected by using NMR; the electrochemical properties of a compound is tested by using a cyclic voltammetry; the spectrum property is detected through an ultraviolet-visible spectrum; the influences of the electrochromic properties of a manufactured electrochromic device and different substituents are inspected; different voltage is applied; different colors are displayed; the electrochromic colors can be achieved through changing different substituents; the compound has a wide application prospect in the field of electrochromism.

Description

technical field [0001] The invention belongs to the technical category of electrochromic materials in the field of functional material preparation, and in particular relates to a multi-color electrochromic material based on four-membered ring pyridines with different substituents, and the application of such derivatives as new electrochromic materials . Background technique [0002] Electrochromic materials refer to the fact that under the action of alternating positive and negative external electric fields or high and low voltages, by extracting or injecting charges (electrons or ions), the materials can be colored in a low transmittance state and fade in a high transmittance state. It is a special phenomenon of a stable and reversible change between states, which is manifested as a reversible change in transparency and color in appearance. Electrochromic devices made of electrochromic materials have some unique characteristics, such as continuously adjustable optical prop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/06C07D213/127C07D213/04C09K9/02
CPCC07D213/04C07D213/06C07D213/127C09K9/02C09K2211/1007C09K2211/1029
Inventor 龚成斌马康唐倩
Owner SOUTHWEST UNIV
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