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Stilbene nitrile derivatives, and preparation method and application thereof

A stilbene nitrile and derivative technology, which is applied in the preparation of carboxylic acid nitrile, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of low reversible temperature, limited application, harmful to the body, etc., and achieves a simple and convenient preparation process. The effect of convenient device preparation and easy color

Active Publication Date: 2012-07-25
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, materials with reversible stimuli-responsive color-changing properties based on molecular packing structures are very limited. Although a small amount of stilbene nitriles have been reported to achieve reversible color adjustment of substances under force, heat, and solvent stimuli, but its 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, (J.Am.Chem.Soc.2010, 132, 13675-13683), which will greatly limit the application of such materials in real life
There are few reports on organic small molecules with low reversible temperature, non-toxic solvents, good reversibility, rapid reversal, and easy preparation.

Method used

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  • Stilbene nitrile derivatives, and preparation method and application thereof
  • Stilbene nitrile derivatives, and preparation method and application thereof
  • Stilbene nitrile derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 4 g (20 mmol) of p-bromonitrile, 3.26 g (12 mmol) of p-methoxybenzaldehyde and sodium methoxide (0.12 g, 2 mmol) were dissolved in 30 ml of chromatographically pure ethanol. Stir the reaction at room temperature and terminate the reaction when there are a large number of solid particles. Then put it into the refrigerator overnight and filter, and the filter cake was washed three times with ethanol to obtain 5.66 g of white powder brominated stilbene nitrile intermediate (IV), with a yield of 90%. Results of substance structure tests: 1 H NMR (500MHz, CDCl 3 ) δ (ppm) 7.78(s, 1H), 7.48(d, J=7.5Hz, 2H), 7.39(d, J=7.5, 2H), 7.34(d, J=7.5, 2H), 6.91(d, J=7.5, 2H), 3.82(s, 1H), ; 13 C NMR (500MHz, CDCl 3 ); δ161.3, 141.2, 132.7, 131.8, 131.0, 126.1, 119.7, 114.5, 106.6, 56.0; MS (EI): m / e 313.0 (M + ).

Embodiment 2

[0044] 1.96 g (10 mmol) of p-bromonitrile benzyl, 1.09 g (8 mmol) of p-methoxybenzaldehyde and sodium methoxide (0.03 g, 0.5 mmol) were dissolved in 30 ml of chromatographically pure ethanol. The reaction was stirred at room temperature until a large number of solid particles terminated the reaction. Then put it in the refrigerator overnight and filter, and rinse the filter cake with ethanol three times to obtain 2.20 g of white powder brominated stilbene nitrile intermediate (IV), with a yield of 70%.

Embodiment 3

[0046] 1.96 g (10 mmol) of p-bromonitrile benzyl, 2.72 g (20 mmol) of p-methoxybenzaldehyde and sodium methoxide (0.03 g, 0.5 mmol) were dissolved in 30 ml of chromatographically pure ethanol. The reaction was stirred at room temperature until a large number of solid particles terminated the reaction. Then put it into the refrigerator overnight and filter, and the filter cake was washed three times with ethanol to obtain 2.98 g of white powder brominated stilbene nitrile intermediate (IV), with a yield of 95%.

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Abstract

The invention relates to a new compound-stilbene nitrile derivatives (I) with reversible stimulus-response discoloring performance, a preparation method thereof, and application as a reversible stimulus-response discoloring material. The compound synthesis method is simple, and can be used for conveniently preparing devices; the pressure-sensitive devices prepared from organic micromolecules discolor under pressure, and can recover easily; and thus, the invention is applicable to the fields of sensors, anti-counterfeiting, storage, display and the like. The invention has blue-green reversible piezallochromy performance, and can implement quick reversion in a heating or organic solvent atmosphere. The preparation process is simple and convenient; and the invention can be widely used in the fields of sensors, anti-counterfeiting, storage, display and the like.

Description

(1) Technical field [0001] The invention relates to a small organic molecule with reversible piezochromic performance, its synthesis method, and its application in pressure-sensitive materials. The color change of the reversible piezochromic organic small molecule of the invention has high contrast, rapid reversal, simple preparation and convenient application, and is suitable for sensors, anti-counterfeiting, storage and displays. (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 a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/43C07C253/30C09K9/02
Inventor 张诚张玉建孙璟玮欧阳密胡彬
Owner ZHEJIANG UNIV OF TECH
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