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Triphenylamine derivative with mechanochromic characteristic and preparation method and application thereof

A technology of triphenylamine and its derivatives, which is applied in the field of triphenylamine derivatives and its preparation, to achieve the effect of good circulation and high contrast

Active Publication Date: 2022-02-18
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, materials with reversible switching, stimuli-responsive color-changing properties based on molecular packing structures are very limited

Method used

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  • Triphenylamine derivative with mechanochromic characteristic and preparation method and application thereof
  • Triphenylamine derivative with mechanochromic characteristic and preparation method and application thereof
  • Triphenylamine derivative with mechanochromic characteristic and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0035] A kind of triphenylamine derivative with mechanochromic property, the name of this triphenylamine derivative is 1,4-bis{[4-4-diphenylamino]1,3,4-oxadiazole}benzene (denoted as DPAOXDBEN), has the structure shown in formula (I):

[0036]

[0037] The preparation method of above-mentioned triphenylamine derivative, comprises the steps:

[0038] 1) Synthesis of 4-dianilinobenzoic acid

[0039] Weigh 5g of 4-dianilinobenzaldehyde and pour it into an Erlenmeyer flask; add 50mL of acetone and water (volume ratio=4:1) mixed solution; slowly add 7.23g of potassium permanganate powder under stirring , and then heated and stirred to reflux for 8 hours. After the reaction is complete, first cool the solution to room temperature, spin the solvent dry with a vacuum rotary evaporator; then add an appropriate amount of distilled water to it, and filter; then add a few drops of 10% hydrochloric acid to the obtained filtrate, stir, and white flocs A precipitate was formed and filt...

Embodiment 2

[0047] To study the molecular mechanofluorescence properties, the solid DPAOXDBEN was ground for about 20 minutes. Such as figure 2 As shown, the fluorescence spectrum of DPAOXDBEN solid has an emission peak at 486nm, and the fluorescence color is cyan. After grinding, the emission peak red shifts to 518nm, and the fluorescence color changes to green. After grinding, the powder is annealed at 150°C for 15 minutes, The fluorescence emission returns to the initial state. It can be used in smart windows, security dyes, optical records, sensors, trademark anti-counterfeiting, memory storage and display fields and other fields.

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PUM

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Abstract

The invention belongs to the technical field of mechanochromic materials, and particularly relates to a triphenylamine derivative with mechanochromic characteristics and a preparation method and application thereof. The triphenylamine derivative is named as 1,4-bis{[4-4-diphenylamino]1,3,4-oxadiazole}benzene, and has a structure shown as a formula (I). The triphenylamine derivative provided by the invention has the characteristics of high contrast ratio, self-recovery and good cyclicity, solves the problem of few stimuli-responsive discoloration materials in the prior art, is used as a novel force-induced discoloration material, changes color under pressure, can realize rapid color recovery under heating adjustment, and can be applied to the fields of intelligent windows, safety dyes, optical recording, sensors, trademark anti-counterfeiting, memory storage, display and the like.

Description

technical field [0001] The invention belongs to the technical field of mechanochromic materials, and in particular relates to a triphenylamine derivative with mechanochromic properties, a preparation method and application thereof. Background technique [0002] Organic small molecule luminescent materials have attracted widespread attention from scientists due to their advantages such as flexible structure changes, adjustable luminescent colors, high luminous efficiency, simple raw materials, good biocompatibility, and thermodynamic stability. As a new type of smart responsive material, its fluorescent color or fluorescent intensity can be adjusted by changing external stimuli such as light, force, pH, heat, ions, etc., so that they can be used in smart windows, safe dyes, optical records, sensors, It has potential applications in the fields of trademark anti-counterfeiting, memory storage and display. Among them, force is a common physical vector, which is clean and pollut...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/107C09K9/02C09K11/06
CPCC07D271/107C09K9/02C09K11/06C09K2211/1014C09K2211/1007C09K2211/1048
Inventor 王海涛徐修楠陈方艺张天任李敏白炳莲
Owner JILIN UNIV
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