Unlock instant, AI-driven research and patent intelligence for your innovation.

Aggregation-induced emission and mechanochromic dye compound and preparation method thereof

A technology of aggregation-induced luminescence and dye compounds, applied in the field of fluorescent dyes, can solve problems such as concentration quenching and discounting of luminous effects

Active Publication Date: 2022-04-26
CHINA THREE GORGES UNIV
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional fluorescent materials will face a concentration quenching (ACQ) problem. When they are made into thin films or solids, the luminous effect will be greatly reduced.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Aggregation-induced emission and mechanochromic dye compound and preparation method thereof
  • Aggregation-induced emission and mechanochromic dye compound and preparation method thereof
  • Aggregation-induced emission and mechanochromic dye compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of L2 Dye Compounds

[0032] 4-(1,2,2Triphenylethenyl)benzaldehyde (1.4g, 4mmol) and thiooxalyl (319mg, 2.7mmol) amine in N,N-dimethylformamide solution, ultrasonic treatment Allow the solid to dissolve completely, heat and stir the reaction in an oil bath at 120°C for 9.5 hours, add a small amount of dichloromethane to the reaction flask after the reaction is complete, filter the reaction solution, dry the solid, and pass through silica gel column chromatography (petroleum ether: two Chloromethane=2:1) ​​separated and spin-dried until solids were precipitated, then the solids were filtered and dried to obtain 430 mg of a yellow-green fluorescent dye with a yield of 26.8%. The H NMR spectrum of the L2 fluorescent dye molecule is as follows figure 1 , The carbon nuclear magnetic resonance spectrum of the L2 fluorescent dye molecule is shown in the figure, and the high-resolution mass spectrum of the L2 fluorescent dye molecule is shown in the figure...

Embodiment 2

[0033] Example 2: Synthesis of L2 Dye Compounds

[0034] 4-(1,2,2Triphenylvinyl)benzaldehyde (1.4g, 4mmol) and thiooxalyl (350mg, 2.9mmol) amine in N,N-dimethylformamide solution, ultrasonic treatment Let the solid dissolve completely, heat and stir the reaction in an oil bath at 120°C for 9.5 hours, add a small amount of dichloromethane into the reaction bottle after the reaction, filter the reaction solution, dry the solid, and pass through silica gel column chromatography (petroleum ether: two Chloromethane=2:1) ​​was separated and spin-dried until a solid was precipitated, then the solid was filtered and dried to obtain 530 mg of a yellow-green fluorescent dye with a yield of 33%. The H NMR spectrum of the L2 fluorescent dye molecule is as follows figure 1 , The carbon nuclear magnetic resonance spectra of L2 fluorescent dye molecules are as follows figure 2 , The high-resolution mass spectrum of L2 fluorescent dye molecule is as follows Figure 5 shown.

Embodiment 3

[0035] Example 3: Synthesis of L2 Dye Compounds

[0036] 4-(1,2,2Triphenylethenyl)benzaldehyde (1.4g, 4mmol) and thiooxalyl (319mg, 2.7mmol) amine in N,N-dimethylformamide solution, ultrasonic treatment Allow the solid to dissolve completely, heat and stir the reaction in an oil bath at 110°C for 9.5 hours, add a small amount of dichloromethane to the reaction flask after the reaction, filter the reaction solution, dry the solid and pass through silica gel column chromatography (petroleum ether: two Chloromethane=2:1) ​​separated and spin-dried until solids were precipitated, then the solids were filtered and dried to obtain 410 mg of a yellow-green fluorescent dye with a yield of 25.5%. The H NMR spectrum of the L2 fluorescent dye molecule is as follows figure 1 , The carbon nuclear magnetic resonance spectra of L2 fluorescent dye molecules are as follows figure 2 , The high-resolution mass spectrum of L2 fluorescent dye molecule is as follows Figure 5 shown.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to an aggregation-induced emission and mechanochromic dye compound and application thereof. The preparation method comprises the following steps: adding 4-(1, 2, 2 triphenylvinyl) benzaldehyde and thiooxamide into an N, N-dimethylformamide solution, stirring and reacting for 9.5 hours at the heating temperature of 120 DEG C, and separating and purifying after the reaction is finished to obtain a fluorescent compound L2; the preparation method comprises the following steps: adding 4-(1, 2, 2 triphenylvinyl) benzaldehyde, thiooxamide and 4-pyridylaldehyde into an N, N-dimethylformamide solution, stirring and reacting for 9 hours at the heating temperature of 120 DEG C, and separating and purifying after the reaction is finished to obtain a fluorescent compound L5; the two synthesized compounds almost have no fluorescence in an organic solvent tetrahydrofuran, have stronger fluorescence in a mixed solvent of the organic solvent tetrahydrofuran and water, have the properties of aggregation-induced emission effect and AIE effect, and can solve the problem of fluorescent material application limitation caused by ACQ effect; the method is of great significance to construction and application of solid fluorescent materials.

Description

technical field [0001] The invention belongs to the field of fluorescent dyes, in particular to an easy-to-synthesize fluorescent dye with remarkable AIE effect and mechanochromic properties. Background technique [0002] In modern life, people's demand for fluorescent materials is increasing, and fluorescent materials have been widely used in photochemical sensors, DNA diagnostics, photochemical sensors, dyes, fluorescent whitening agents, organic electroluminescent devices (OLEDs), etc. Traditional fluorescent materials will face a concentration quenching (ACQ) problem. When they are made into thin films or solids, the luminous effect will be greatly reduced. The emergence of aggregation-induced emission (AIE) materials has perfectly solved this problem. Among them, tetraphenylethylene (TPE), as an AIE "star molecule", is simple to synthesize, easy to realize functionalization, and can be easily combined with other fluorophores. Fluorescent compounds with excellent proper...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D513/04C09B23/14C09K11/06C09K9/02
CPCC07D513/04C09B23/148C09K11/06C09K9/02C09K2211/1007C09K2211/1051C09K2211/1029Y02E10/542
Inventor 郑开波李鋆余威肖宇峰王丽红
Owner CHINA THREE GORGES UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com