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Diphenylethylene type co-crystallization materials with multi-stimulus fluorescence response property and preparation method thereof

A fluorescent response, stilbene technology, applied in the direction of color-changing fluorescent materials, luminescent materials, halogenated hydrocarbon preparation, etc., can solve the problems of unpredictability of luminescent color, complex spatial structure, etc., and achieve the effect of broadening the application space and the scope of preparation

Inactive Publication Date: 2014-03-19
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the complexity of the spatial structure of molecules when they form solids, the solid-state emission colors of stilbene compounds are often unpredictable.

Method used

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  • Diphenylethylene type co-crystallization materials with multi-stimulus fluorescence response property and preparation method thereof
  • Diphenylethylene type co-crystallization materials with multi-stimulus fluorescence response property and preparation method thereof
  • Diphenylethylene type co-crystallization materials with multi-stimulus fluorescence response property and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1) Weigh 0.0332g of (1,4’-bis[2-(o-cyanophenyl)vinyl]benzene) and 0.0544g of 4-bromo-2,3,5,6-tetrachlorobenzoic acid respectively;

[0026] 2) Mix the two evenly, put them into a ball mill (MM200 from Laich Company, Germany), add 30 μL of chloroform, and grind for 30 minutes at 20 r / s;

[0027] 3) Dissolve the ground powder in 20mL of chloroform, place it at room temperature, and wait for the solvent to evaporate to obtain a single crystal product.

[0028] 4) Characterize the product:

[0029] Carry out powder XRD test to the powder of product, and diffraction pattern shows that new substance is produced; Carry out single crystal X-ray diffraction analysis to single crystal product and know, (1,4'-bis[2-(o-cyanophenyl)vinyl ]benzene) and 4-bromo-2,3,5,6-tetrachlorobenzoic acid are bound together by intermolecular hydrogen bonds to form a new crystal structure;

[0030] Analyzing and measuring the fluorescence spectra of product powders exposed to different solvents s...

Embodiment 2

[0033] 1) Weigh 0.0664g of (1,4-bis-p-(cyanostyrene)-benzene) and 0.1088g of octafluoronaphthalene;

[0034] 2) Mix the two evenly, put them into a ball mill (Leicher MM200, Germany), add 30 μL of chloroform, and grind for 30 minutes at 30 r / s;

[0035] 3) Dissolve the ground powder in 10mL of chloroform, place it at room temperature, and wait for the solvent to evaporate to obtain a single crystal product.

[0036] 4) Characterize the product:

[0037] The powder of the product was tested by PXRD, and the diffraction pattern showed that new substances were produced; the single crystal X-ray diffraction analysis of the single crystal product showed that (1,4-bis-p-(cyanostyrene)-benzene) Combined with octafluoronaphthalene through intermolecular halogen bonds to form a new crystal structure;

[0038] Different solvents are added dropwise to the product powder for fluorescence spectrum measurement, and different products have specific responses to different solvents. ( ima...

Embodiment 3

[0040] 1) Weigh 0.0664g (1-o-cyano-styryl, 4-p-cyano-styryl) benzene and 0.1088g octafluoronaphthalene;

[0041] 2) Mix the two evenly, put them into a ball mill, add 3 drops of chloroform, and grind at 20r / s for 30min;

[0042] 3) Take about 0.1 g of the ground powder and dissolve it in 10 mL of chloroform, place it at room temperature, and wait for the solvent to evaporate to obtain a single crystal product.

[0043] 4) Characterize the product:

[0044] The XRD test was carried out on the powder of the product, and the diffraction pattern showed that new substances were produced; the single crystal X-ray diffraction analysis of the single crystal product showed that (1-o-cyano styryl, 4-p-cyano styryl) Benzene and octafluoronaphthalene produced co-crystals through intermolecular interactions, forming a new crystal structure;

[0045]The product single crystal was placed under full-spectrum light conditions (light source: Zhongjiao Jinyuan CEL-HXB300 / UV300; 20mA), illumina...

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Abstract

The invention discloses a series of cyano-substituted diphenylethylene type co-crystallization compounds with multi-stimulus fluorescence response property and a preparation method thereof, belonging to the field of crystalline materials with subject and object structures. The novel crystalline compounds are obtained by selecting a cyano-substituted diphenylethylene compound as a subject, taking a series of organic small molecular compounds with hydroxyl, carboxyl and other groups or halogenated benzene and the like as objects, and performing co-crystallization by subject and object identification and intermolecular interaction. The compounds disclosed by the invention are characterized in that the selected cyano-substituted diphenylethylene compound has excellent optical property, the co-crystallization materials can be obtained by the action of frictional force, the ultrasonic action, solvent volatilization and other methods, and the precise crystal structures can be determined; and simultaneously, the series of the co-crystallization materials have reversible fluorescence response against a variety of external stimuli (such as light, pressure, organic solvents and the like). The compounds have application prospects in the fields of manufacturing of optical anti-counterfeiting materials, fluorescent sensors and optoelectronic devices, and the like.

Description

technical field [0001] The invention belongs to the field of molecular solid fluorescent materials, and provides a new design idea and feasible scheme for the preparation of novel multi-stimulus fluorescence response multi-element molecular crystal materials, especially the preparation of a series of cyano-substituted stilbene-type multi-crystal compounds method. Background technique [0002] Organic fluorescent materials with stimuli-response functions have gradually attracted extensive attention from industry and academia due to their sensitive and fast response signals. Such materials have important application value in the fields of sensors and optical anti-counterfeiting. In recent years, adjusting the arrangement mode of molecules by changing external conditions has gradually become the main strategy for designing and preparing such stimuli-responsive functional materials. For example, in 2005, Mutai et al. reported that molecular solids can change their fluorescence ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K9/02C09K11/06C07C253/34C07C255/51C07C255/50C07C51/43C07C63/70C07C17/392C07C25/22
Inventor 闫东鹏范国凌林禾阳唐彦群陈莘楷马骏
Owner BEIJING UNIV OF CHEM TECH
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