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Cyanostilbene fluorescence epoxy compound, and preparation method and application thereof

A cyanostilbene, oxygen compound technology, applied in chemical instruments and methods, epoxy resin glue, epoxy resin coating and other directions, can solve problems such as single type

Active Publication Date: 2019-11-05
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the currently reported fluorescent epoxy resins with AIE properties use tetraphenylethylene as the fluorescent light-emitting group, and the species is single. Therefore, it is of great significance to prepare new fluorescent epoxy resins with aggregation-induced luminescence or aggregation-induced fluorescence enhancement properties.

Method used

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  • Cyanostilbene fluorescence epoxy compound, and preparation method and application thereof
  • Cyanostilbene fluorescence epoxy compound, and preparation method and application thereof
  • Cyanostilbene fluorescence epoxy compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] One-pot Preparation of Cyanostilbene Fluorescent Epoxy Compound C-1

[0063] Add p-hydroxybenzaldehyde (0.01mol, 1.22g), p-hydroxybenzonitrile (0.01mol, 1.33g) and epichlorohydrin (0.10mol, 9.25g) into a 100mL single-necked bottle in turn, and heat up to 68°C. After the raw materials are dissolved, add tetrabutylammonium bromide (0.001mol, 0.322g), react for 4 to 6 hours, add 100mL of ethanol, stir for 10 minutes, then add potassium tert-butoxide (0.01mol, 1.12g), continue The reaction was stopped for 4 hours. After the temperature of the reaction system dropped to room temperature, the solid product was collected by suction filtration to obtain a crude product, which was recrystallized with 80 mL of ethanol to obtain 2.23 g of a pure product with a yield of 64%.

Embodiment 2

[0065] The Step-by-Step Preparation of Cyanostilbene Fluorescent Epoxy Compound C-1

[0066] (1) Preparation of 4-(2-oxirane methoxy) benzaldehyde

[0067] Add p-hydroxybenzaldehyde (0.01mol, 1.22g) and epichlorohydrin (0.10mol, 9.25g) into a 100mL single-necked bottle with a magnet, raise the temperature to 68°C, and add tetrabutyl bromide after the raw materials are dissolved Ammonium chloride (0.001mol, 0.322g), reacted for 6 hours, and then added 15% aqueous sodium hydroxide solution (0.02mol, 0.80g), and continued to react for 3 hours, then stopped the reaction. Add 60 mL of toluene and stir for 10 minutes, release the lower water layer with a separatory funnel, wash the organic phase twice with water, collect the organic phase layer and spin dry the solvent to obtain the crude product, which is separated by column with dichloromethane as the eluent, 1.6 g of pure product was obtained, yield 89%.

[0068] (2) Preparation of 4-(2-oxirane methoxy) benzyl nitrile

[0069]...

Embodiment 3

[0073] One-pot Preparation of Cyanostilbene Fluorescent Epoxy Compound C-2

[0074]Add p-hydroxybenzaldehyde (0.01mol, 1.22g) and epichlorohydrin (0.10mol, 9.25g) into a 250mL single-necked bottle with a magnet, heat up to 68°C, and add tetrabutyl Ammonium bromide (0.001mol, 0.322g), after reacting for 8 hours, add terephthalonitrile (0.0045mol, 0.7000g) and 150mL of ethanol, after stirring for 10 minutes, add solid sodium hydroxide (0.03mol, 1.20g) , Stop the reaction after continuing to react for 4 to 6 hours. After the temperature of the reaction system dropped to room temperature, the solid product was collected by suction filtration, washed with water, and dried to obtain the crude product, which was recrystallized with a mixed solvent of DMF and ethanol (V:V=3:1) to obtain the yellow pure product 1.95 g, yield 93%.

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Abstract

The invention discloses a cyanostilbene fluorescence epoxy compound having AIEE properties, and a preparation method and an application thereof. The compound is prepared by a step-by-step process, that is, a benzaldehyde or phenylacetonitrile compound containing an epoxy group is prepared by a substitution reaction and a ring closure reaction, and then a Knoevenagel condensation reaction is carried out to prepare the cyanostilbene fluorescence epoxy compound; or the compound is prepared by a one-pot process, that is, all the raw materials are mixed, and then the obtained mixture undergoes thesubstitution reaction, the ring closure reaction and the Knoevenagel condensation reaction to prepare the compound. The cyanostilbene fluorescence epoxy compound of the invention has the advantages ofsimple synthesis route, easiness in purification, high yield and low preparation cost, also has the AIEE properties, can emit strong fluorescence when in the aggregate state, and has wide applicationprospects in the fields of fluorescent coatings, fluorescent casting materials, fluorescent adhesives and fluorescent laminates.

Description

technical field [0001] The invention relates to the preparation of luminescent materials, in particular to a cyano-stilbene fluorescent epoxy compound and its preparation method and application. [0002] technical background [0003] Fluorescent epoxy resin has both the properties of epoxy resin and the excellent luminescent properties of fluorescent luminescent substances, and fluorescent epoxy resin can emit fluorescence at a certain excitation wavelength. The traditional fluorescent epoxy resin achieves its luminous performance by doping fluorescent light-emitting substances in ordinary resins. Generally, the fluorescent light-emitting substances mixed are divided into two categories: inorganic and organic. Inorganic fluorescent light-emitting substances have high luminous efficiency and good thermal stability, but have poor compatibility with epoxy resin, are difficult to process and shape, and the fluorescent powder is easy to fall off. . Organic light-emitting substan...

Claims

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Application Information

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IPC IPC(8): C07D303/27C09K11/06C09D163/00C09D5/22C09J163/00C08L63/00
CPCC07D303/27C09K11/06C09D163/00C09D5/22C09J163/00C08L63/00C09K2211/1007C09K2211/1088
Inventor 张海良谭会平袁勇杰杨博豪
Owner XIANGTAN UNIV
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