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A kind of triphenylamine derivative and its preparation method and application

A derivative, triphenylamine technology, applied in the field of triphenylamine derivatives and its preparation and application, can solve the problems of limited material application, and achieve the effects of good cycle, high contrast, and convenient device preparation

Active Publication Date: 2017-04-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the reversible piezochromic phenomenon reported so far is mainly the fluorescent color change of materials under the action of external force, and there are few pressure-controllable changes in fluorescent color and intensity; in addition, the reversible temperature is generally greater than 100°C,( J.Am.Chem.Soc.2010,132,13675–13683) will greatly limit the application of such materials

Method used

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  • A kind of triphenylamine derivative and its preparation method and application
  • A kind of triphenylamine derivative and its preparation method and application
  • A kind of triphenylamine derivative and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Dissolve 0.92g (5mmol) of p-bromobenzaldehyde (II), 2.17g (7.5mmol) of triphenylamine 4-boronate, and 0.1122g (0.5mmol) of palladium acetate in 10mL of deionized water / 20mL of isopropanol, and add phosphoric acid Tripotassium 1g (4.7mmol). In an air environment, react at room temperature for 11 minutes. After the reaction was quenched with saturated brine, it was extracted three times with ethyl acetate, the organic phases were combined, washed with saturated brine, and finally dried over anhydrous magnesium sulfate. Filtration, the filtrate was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography, eluted with a mixed solvent with a volume ratio of petroleum ether / ethyl acetate of 30:1, and the eluent containing the product was collected, and the eluent was decompressed After evaporating the solvent, 1.57 g of product (I) was obtained as a yellow powder, with a yield of 90%. The structural confirmation of the substance...

Embodiment 2

[0043]Dissolve 0.92 g (5 mmol) of p-bromobenzaldehyde (II), 1.156 g (4 mmol) of triphenylamine 4-boronate, and 0.11 g (0.5 mmol) of palladium palladium acetate in 6.5 mL of deionized water / 13.5 mL of isopropanol, 1 g (4.7 mmol) of tripotassium phosphate was added. In an air environment, react at room temperature for 11 minutes. After the reaction was quenched with saturated brine, it was extracted three times with ethyl acetate, the organic phases were combined, washed with saturated brine, and finally dried over anhydrous magnesium sulfate. Filtration, the filtrate was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography, eluted with a mixed solvent with a volume ratio of petroleum ether / ethyl acetate of 30:1, and the eluent containing the product was collected, and the eluent was evaporated under reduced pressure After solvent removal, 1.4 g of yellow powder product (I) was obtained with a yield of 75%.

Embodiment 3

[0045] The triphenylamine derivatives solid powder (I) 0.1g that the embodiment of the present invention makes is spread on the quartz plate or is placed in the mortar, shows sky-blue fluorescence under the ultraviolet lamp, when subjected to molybdenum scraping shear force or pestle After the action, the fluorescent color under the ultraviolet lamp changes to grass green, remove the external force, and the stressed part still maintains grass green fluorescence. The photographs under UV light before and after normal pressure grinding and the solid-state fluorescence spectrum are as follows: figure 1 shown.

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Abstract

The invention discloses a triphenylamine derivative and a preparation method thereof. The triphenylamine derivative (I) has the inverse-force fluorescence conversion stimulation performance and can serve as an inverse-force fluorescence conversion stimulation material.

Description

[0001] (1) Technical field [0002] The invention relates to a triphenylamine derivative, a preparation method thereof and an application as a reversible force-stimulated fluorescent conversion material, which is suitable for sensors, anti-counterfeiting, storage and displays. [0003] (2) Background technology [0004] When an external force is applied to the material, the phenomenon that the fluorescent color of the material changes is called piezochromism. Substances with piezochromism have at least two stable or metastable accumulation modes affected by pressure. When stimulated by a force, the conformation of the molecule changes, resulting in a change in the molecular packing method, or the material changes from one ordered structure to another ordered or partially ordered or disordered structure, and the photophysical properties of the material change with time. changes. Then, after being treated with heating and solvents, the accumulation mode of the molecules will ret...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C221/00C07C223/06C09K9/02
Inventor 张诚占玲玲欧阳密孙璟玮吕晓静
Owner ZHEJIANG UNIV OF TECH
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