Purpurine derivative electrochromic and electrofluorescent color-changing material as well as preparation method and application thereof

An electrochromic and derivative technology, used in color-changing fluorescent materials, chemical instruments and methods, optics, etc., can solve the problems of reducing the electrochromic voltage, unable to give viologen derivatives electrofluorescence color performance, etc. Optical contrast, excellent discoloration performance, effect of reducing discoloration voltage

Active Publication Date: 2022-03-04
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The invention introduces pyrrole and carbazole groups, which improves the electron-deficient state on the core group 4,4'bipyridine of the viologen compound, reduces its electrochromic voltage; and can obtain a bipolar electrochromic device, realizing Higher contrast, with multiple color changes; however, the electrochromic materials provided by this technology have a high driving voltage (>1.4V), and at the same time, since pyrrole and carbazole are not fluorescent groups, they cannot impart viologen derivatives. Electroluminescence color change properties

Method used

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  • Purpurine derivative electrochromic and electrofluorescent color-changing material as well as preparation method and application thereof
  • Purpurine derivative electrochromic and electrofluorescent color-changing material as well as preparation method and application thereof
  • Purpurine derivative electrochromic and electrofluorescent color-changing material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Preparation of Viologen Derivative Electrochromic and Electrofluorochromic Bifunctional Material (A) 1,1'-(4-Benzimidazolylphenyl)-4,4'-Bipyridyl Dihexafluorophosphate method, comprising the steps of:

[0045] 1) Add 2.5g benzimidazole, 3.3g p-fluoronitrobenzene, 3.3g potassium carbonate, 60mlDMF in a 100ml three-necked flask, 2 Stir at room temperature for 30 minutes under an atmosphere, then rise to 110°C, heat to reflux for 24 hours; after the reaction is completed, cool the solution to room temperature, add cold water, precipitate, filter, and obtain a precipitate; wash with deionized water and petroleum ether successively Precipitate 3 times; cross silica gel chromatography column with ethyl acetate-petroleum ether (1:2, v / v) eluent, obtain yellow powder product N-(4-nitrophenyl) benzimidazole, yield 96%;

[0046] MS: m / z=240.1

[0047] 1 H NMR (DMSO-d 6 ,600MHz,ppm)δ8.75(s,1H),8.47(d,2H),8.04(d,2H),7.80(dd,2H),7.39(dt,2H).

[0048] 2) Add 3.0g N-(4-nitrophen...

Embodiment 2

[0066] Preparation of Viologen Derivative Electrochromic and Electrofluorochromic Bifunctional Material (A) 1,1'-(4-Benzimidazolylphenyl)-4,4'-Bipyridyl Dihexafluorophosphate method, comprising the steps of:

[0067] 1) Add 2.0g benzimidazole, 3.0g p-fluoronitrobenzene, 3.0g potassium carbonate, 60mlDMF in a 100ml three-necked flask, 2 Stir at room temperature for 30 minutes under an atmosphere, then rise to 110°C, heat to reflux for 24 hours; after the reaction is completed, cool the solution to room temperature, add cold water, precipitate, filter, and obtain a precipitate; wash with deionized water and petroleum ether successively Precipitate 3 times; cross silica gel chromatography column with ethyl acetate-petroleum ether (1:2, v / v) eluent, obtain yellow powder product N-(4-nitrophenyl) benzimidazole, yield 90%;

[0068] MS: m / z=240.1

[0069] 1 H NMR (DMSO-d 6 ,600MHz,ppm)δ8.75(s,1H),8.47(d,2H),8.04(d,2H),7.80(dd,2H),7.39(dt,2H).

[0070] 2) Add 1.5g N-(4-nitrophen...

Embodiment 3

[0087] Preparation of Viologen Derivative Electrochromic and Electrofluorochromic Bifunctional Material (A) 1,1'-(4-Benzimidazolylphenyl)-4,4'-Bipyridyl Dihexafluorophosphate method, including the following steps:

[0088] 1) Add 4.0g benzimidazole, 6.0g p-fluoronitrobenzene, 6.0g potassium carbonate, 80mlDMSO in a 100ml three-necked flask, 2 Stir at room temperature for 30 minutes under an atmosphere, then rise to 110°C, heat to reflux for 24 hours; after the reaction is completed, cool the solution to room temperature, add cold water, precipitate, filter, and obtain a precipitate; wash with deionized water and petroleum ether successively Precipitate 3 times; cross silica gel chromatography column with ethyl acetate-petroleum ether (1:5, v / v) eluent, obtain yellow powder product N-(4-nitrophenyl) benzimidazole, yield 85%;

[0089] MS: m / z=240.1

[0090] 1 H NMR (DMSO-d 6 ,600MHz,ppm)δ8.75(s,1H),8.47(d,2H),8.04(d,2H),7.80(dd,2H),7.39(dt,2H).

[0091] 2) Add 2.0g N-(4-ni...

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Abstract

The invention discloses a viologen derivative electrochromic and electrofluorescent discoloration bifunctional material as well as a preparation method and application thereof. The preparation method comprises the following steps: by taking 4, 4 '-dipyridyl as a raw material, carrying out nucleophilic substitution reaction on the 4, 4'-dipyridyl and 1-chloro-2, 4-dinitrobenzene to generate Zincke salt; carrying out nucleophilic substitution reaction on p-fluoronitrobenzene and a nitrogen-containing aromatic heterocyclic ring to generate a nitro compound, and reducing the nitro compound into an amino compound by using hydrazine hydrate as a reducing agent; and performing Zincke reaction on products of the two-step reaction to generate a target product. According to the invention, a benzimidazole group with an electron donating effect is introduced into a viologen derivative, and forms an electron donating-electron withdrawing effect with an electron-deficient bipyridine group, so that the color change voltage is reduced, and the optical contrast is improved; meanwhile, an electrofluorescence discoloration function is introduced into the viologen derivative.

Description

technical field [0001] The invention relates to an electrochromic and electroluminescent material, in particular to a viologen derivative as a dual-functional material of electrochromic and electroluminescent and a preparation method thereof, which belongs to the technical field of photoelectric materials. Background technique [0002] Electrochromic materials can achieve their optical properties, including reversible changes in transparency, reflectivity and color, under the drive of several volts, making them useful in the fields of microelectronics, energy-saving buildings, automobile industry, national defense and aerospace, etc. Broad application prospects. As an emerging industrialization technology, the potential market of electrochromic technology is huge, and it will definitely have a non-negligible and far-reaching impact on industrial upgrading, industry development, and even the national economy. The electroluminescent discoloration refers to the reversible chan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C09K9/02G02F1/1516
CPCC07D401/14C09K9/02G02F1/1516C09K2211/1029C09K2211/1044
Inventor 叶炜杰刘平张雪健郭旭
Owner SOUTH CHINA UNIV OF TECH
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