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Bile acid-salicylaldehyde aniline conjugate, preparation method and application thereof, and solid-state photoluminescent color-changing anti-counterfeiting method based on it

A technology of salicylaldehyde aniline and conjugates, which is applied in the fields of cholic acid-salicylaldehyde aniline conjugates, solid-state photofluorescence color change anti-counterfeiting, and can solve the problems that the molecular conformation has a great influence and limits practical applications.

Active Publication Date: 2021-01-19
XI AN JIAOTONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some of these compound solids are thermochromic and some are photochromic, which are greatly affected by molecular conformation.
Planar close-packed molecules generally have thermochromic properties, and intramolecular proton transfer occurs in the ground state, changing from enol to cis-ketone configuration, but the extremely low experimental temperature (about 77K) greatly limits its practical application

Method used

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  • Bile acid-salicylaldehyde aniline conjugate, preparation method and application thereof, and solid-state photoluminescent color-changing anti-counterfeiting method based on it
  • Bile acid-salicylaldehyde aniline conjugate, preparation method and application thereof, and solid-state photoluminescent color-changing anti-counterfeiting method based on it
  • Bile acid-salicylaldehyde aniline conjugate, preparation method and application thereof, and solid-state photoluminescent color-changing anti-counterfeiting method based on it

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] The preparation method of cholic acid-salicylaldehyde aniline conjugate of the present invention comprises the following steps:

[0112] 1) Weigh cholic acid, 2,4-dihydroxybenzaldehyde, 4-dimethylaminopyridine, dicyclohexylcarbodiimide and dichloromethane, and mix cholic acid, 2,4-dihydroxybenzaldehyde, 4 -Dimethylaminopyridine and dicyclohexylcarbodiimide are dispersed in dichloromethane to obtain reaction mixture a, in which, cholic acid, 2,4-dihydroxybenzaldehyde, 4-dimethylaminopyridine, dicyclohexylcarbodiimide The ratio of diimine and dichloromethane is 2.0g: 1.0g: 61mg: 1.5g: 10mL;

[0113] 2) The reaction mixture a obtained in step 1) was stirred and reacted at room temperature. After the reaction was completed, it was filtered and the solvent was removed, and the cholic acid-salicylaldehyde conjugate was obtained as a white powder solid after elution by column chromatography;

[0114] 3) Weigh the cholic acid-salicylaldehyde conjugate, 4,4'-diaminobiphenyl and...

Embodiment 2

[0123] The preparation method of cholic acid-salicylaldehyde aniline conjugate of the present invention comprises the following steps:

[0124] 1) Weigh cholic acid, 2,4-dihydroxybenzaldehyde, 4-dimethylaminopyridine, dicyclohexylcarbodiimide and dichloromethane, and mix cholic acid, 2,4-dihydroxybenzaldehyde, 4 -Dimethylaminopyridine and dicyclohexylcarbodiimide are dispersed in dichloromethane to obtain reaction mixture a, wherein, cholic acid, 2,4-dihydroxybenzaldehyde, 4-dimethylaminopyridine, dicyclohexylcarbodiimide The ratio of diimine and dichloromethane is 2.0g:0.7g:183mg:1.0g:50mL;

[0125] 2) The reaction mixture a obtained in step 1) was stirred and reacted at room temperature. After the reaction was completed, it was filtered and the solvent was removed, and the cholic acid-salicylaldehyde conjugate was obtained as a white powder solid after elution by column chromatography;

[0126] 3) Weigh the cholic acid-salicylaldehyde conjugate, 4,4'-diaminobiphenyl and eth...

Embodiment 3

[0135] The preparation method of cholic acid-salicylaldehyde aniline conjugate of the present invention comprises the following steps:

[0136] 1) Weigh cholic acid, 2,4-dihydroxybenzaldehyde, 4-dimethylaminopyridine, dicyclohexylcarbodiimide and dichloromethane, and mix cholic acid, 2,4-dihydroxybenzaldehyde, 4 -Dimethylaminopyridine and dicyclohexylcarbodiimide are dispersed in dichloromethane to obtain reaction mixture a, in which, cholic acid, 2,4-dihydroxybenzaldehyde, 4-dimethylaminopyridine, dicyclohexylcarbodiimide The ratio of diimine and dichloromethane is 2.0g: 0.85g: 100mg: 1.3g: 30mL;

[0137] 2) The reaction mixture a obtained in step 1) was stirred and reacted at room temperature. After the reaction was completed, it was filtered and the solvent was removed, and the cholic acid-salicylaldehyde conjugate was obtained as a white powder solid after elution by column chromatography;

[0138] 3) Weigh the cholic acid-salicylaldehyde conjugate, 4,4'-diaminobiphenyl a...

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Abstract

The invention discloses a cholic acid-salicylaldehyde anil conjugate, a preparation method and application thereof and a solid-state photochromic color-variable anti-counterfeiting method based on thecholic acid-salicylaldehyde anil conjugate. When the conjugate is excited by 395nm ultraviolet light, the conjugate solid emits yellow-green fluorescence; after the conjugate is irradiated for 10minby a 365nm ultraviolet lamp, the fluorescence emitted by the conjugate solid is changed into orange red from yellow green; after the conjugate is irradiated by 532nm laser for 10min, the fluorescenceemitted by the conjugate solid is recovered from orange red to yellow green; under natural light, the solid color of the conjugate is yellow, and the original color is kept in the whole illumination process. The conjugate and the anti-counterfeiting method based on the conjugate can realize generation, color change and transformation of anti-counterfeiting patterns, the preparation method is simple and efficient, synthesis cost is low, and color change of photoinduced fluorescence at a solid state is sensitive, rapid and reversible and has good fatigue resistance.

Description

technical field [0001] The present invention relates to a conjugate, its preparation method and application, and an anti-counterfeiting method based on it, in particular to a cholic acid-salicylaldehyde aniline conjugate, its preparation method and application, and solid-state photoluminescence based on it Discoloration anti-counterfeiting method. Background technique [0002] Photochromic materials refer to materials whose color or fluorescence properties change under the action of light. At present, photochromic materials have been widely concerned by researchers at home and abroad because of their potential huge application prospects in the fields of anti-counterfeiting technology, security ink, optical information storage, light-regulated switches, and biological imaging. The structure of spiropyran, azobenzene, and heterocyclic diarylethene is an earlier and more widely studied system in organic photochromic materials (Chem. Rev. 2018, 118, 10710; Chem. Soc. Rev. 2018,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J43/00C09K11/06C09K9/02C09D5/22C09D5/30B41M3/14
CPCB41M3/142C07J43/003C09D5/22C09D5/30C09K9/02C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014
Inventor 张祯邵利平金励铭郭晓强
Owner XI AN JIAOTONG UNIV
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