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Tristyrene nitrile derivative as well as preparation method and application thereof

A technology for tristyryl nitrile and derivatives, which is applied to tristyryl nitrile derivatives and the fields of preparation and application thereof, can solve the problems of low reversible temperature, limited application, harmful to health, etc., and achieves simple preparation process, convenient preparation of devices, high contrast effect

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

AI Technical Summary

Problems solved by technology

[0005] But so far, the reported materials with reversible piezochromic properties based on molecular packing structure are very limited. Although a small amount of triphenylene nitriles have been reported to achieve reversible color adjustment of materials under force, heat, and solvent stimulation, but Most of the solvents used are toxic solvents, such as tetrahydrofuran, dichloromethane, methanol, etc., which are harmful to the body and are rarely used in family life.
In addition, the reversible temperature must be greater than 100°C, which greatly limits the application of such materials in real life.
There are few reports on small organic molecules with low reversible temperature, non-toxic solvents, good reversibility, rapid reversal, and easy preparation

Method used

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  • Tristyrene nitrile derivative as well as preparation method and application thereof
  • Tristyrene nitrile derivative as well as preparation method and application thereof
  • Tristyrene nitrile derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 2-(4-bromophenyl)-3,3-diphenylacrylonitrile 1.2g (6mmol), tetrakistriphenylphosphine palladium 0.03g (0.03mmol), p-methoxyphenylboronic acid 1.47g (12mmol), carbonic acid Sodium aqueous solution (2.0M, 1.8mL) was dissolved in 50mL of toluene, reacted at 90°C for 24h under the protection of high-purity nitrogen, after the reaction was completed, cooled, separated the organic phase, extracted with dichloromethane, combined the organic phase, and washed three times with saturated brine , dried over anhydrous sodium sulfate, left standing overnight, filtered, and the concentrated crude product was separated by column chromatography [V (petroleum ether) / V (ethyl acetate)=50 / 1] to obtain the target product 1.08g, the yield was 65.7%. 1 H NMR (500MHz, CDCl 3 )δ7.53(d,J=8.8Hz,2H),7.51-7.47(m,2H),7.48-7.42(m,5H),7.34(d,J=8.4Hz,2H),7.30(t,J =7.3Hz,1H),7.24(t,J=7.4Hz,2H),7.09(d,J=7.2Hz,2H),6.99(d,J=8.8Hz,2H),3.87(s,3H). 13 C NMR (125MHz, CDCl 3 )δ159.47,157.33,140.54,140.52,13...

Embodiment 2

[0037] 2-(4-bromophenyl)-3,3-diphenylacrylonitrile 2.0g (10mmol), tetrakistriphenylphosphine palladium 0.05g (0.05mmol), p-methoxyphenylboronic acid 3.05g (25mmol), carbonic acid Sodium aqueous solution (2.0M, 3.0mL) was dissolved in 60mL of toluene, reacted at 90°C for 24h under the protection of high-purity nitrogen, after the reaction was completed, cooled, separated the organic phase, extracted with dichloromethane, combined the organic phase, and washed three times with saturated brine , dried over anhydrous sodium sulfate, left to stand overnight, filtered, and the concentrated crude product was separated by column chromatography [V (petroleum ether) / V (ethyl acetate)=50 / 1] to obtain 1.92 g of the target product, the yield 70%.

Embodiment 3

[0039] 2-(4-bromophenyl)-3,3-diphenylacrylonitrile 3.0g (15mmol), tetrakistriphenylphosphine palladium 0.075g (0.075mmol), p-methoxyphenylboronic acid 4.5g (37mmol), carbonic acid Sodium aqueous solution (2.0M, 4.0mL) was dissolved in 80mL of toluene, and reacted at 90°C for 24h under the protection of high-purity nitrogen. After the reaction was completed, cooled, separated the organic phase, extracted with dichloromethane, combined the organic phase, and washed three times with saturated brine , dried over anhydrous sodium sulfate, left to stand overnight, filtered, and the concentrated crude product was separated by column chromatography [V (petroleum ether) / V (ethyl acetate)=50 / 1] to obtain 2.79 g of the target product, the yield 68%.

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Abstract

The invention discloses a tristyrene nitrile derivative as well as a preparation method and application thereof. The structure of the tristyrene nitrile derivative is as shown in a formula (I). The preparation method comprises a step that the tristyrene nitrile derivative as shown in the formula (I) is generated from 2-(4-bromobenzene)-3,3-diacrylonitrile as shown in a formula (II) and p-methoxy phenylboronic acid as shown in a formular (III) in the presence of tetrakispalladium and sodium carbonate through Suzuki coupling reaction. The invention further provides the application of the tristyrene nitrile derivative as a reversible piezallochromy material. The synthesized tristyrene nitrile derivative not only has the reversible piezallochromy property between blue-green and light orange-yellow, but also can be rapidly reverted in heating or organic solvent atmosphere, the preparation process is simple and convenient, components can be conveniently prepared, and the tristyrene nitrile derivative is widely applied to the fields of sensors, fake prevention, storage, display and the like.

Description

(1) Technical field [0001] The invention relates to a tristyrene nitrile derivative, its preparation method and its application as a reversible piezochromic material. (2) Background technology [0002] When pressure is applied, the color changes, and this unique phenomenon makes piezochromic substances present great commercial prospects in the fields of sensing, anti-counterfeiting, storage and display. [0003] When pressure is applied to the piezochromic substance, the interaction force between molecules changes, which causes the transformation of the accumulation mode of the solid substance and changes the emission spectrum. When a crystalline solid undergoes a transition from one crystalline structure to another crystalline structure or an amorphous structure, a discontinuous change in color occurs, and when heated or placed in an organic solvent atmosphere, it returns to its original packing mode and achieves Reversible piezochromism. Pressure can also affect the coor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/37C07C253/30C09K9/02
Inventor 张诚吴启超占玲玲欧阳密孙璟玮
Owner ZHEJIANG UNIV OF TECH
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