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Toluylene nitrile derivative with D-A structure and synthesis method and application thereof

A stilbene nitrile and synthesis method technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve the effects of convenient preparation of devices, simple synthesis method, and good recyclability

Active Publication Date: 2014-11-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the fluorescent materials with reversible piezochromic phenomenon reported from the molecular structure are very limited. In this paper, a class of stilbene nitrile derivatives with a D-A structure is designed, which show red light in solvents of different polarities- The change of yellow light (polar to non-polar), and the substance precipitated from the corresponding solvent shows the same color change; at the same time, the substance realizes the opening of fluorescence under external stimulation and can recover by itself under certain conditions. In real life There is a wide range of application value in

Method used

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  • Toluylene nitrile derivative with D-A structure and synthesis method and application thereof
  • Toluylene nitrile derivative with D-A structure and synthesis method and application thereof
  • Toluylene nitrile derivative with D-A structure and synthesis method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0039] Dissolve 4 g (20 mmol) of p-bromonitrile (20 mmol), 1.57 g (12 mmol) of 4-cyanobenzaldehyde and 0.12 g (2 mmol) of sodium methoxide in 30 mL of chromatography-grade ethanol. Stir the reaction at room temperature and terminate the reaction when there are a large number of solid particles. The reaction solution was directly filtered, and the filter cake was recrystallized with absolute ethanol to obtain 3.34 g of brominated stilbene nitrile intermediate represented by formula (V), with a yield of 90%. Results of substance structure tests: 1 H NMR (500 MHz, CDCl 3 ) δ 7.98 (d, J = 8.5 Hz, 2H), 7.77 (d, J = 8.5 Hz, 2H), 7.62 (d, J = 9.0 Hz, 2H), 7.58 (d, J = 9.0 Hz, 2H), 7.54 (s, 1H); 13 C NMR (125 MHz, CDCl 3 ) δ 139.7, 137.5, 132.7, 132.5, 132.4, 129.6, 127.7, 124.5, 118.1, 116.8, 114.3, 113.8; MS(EI): m / z 308.0[M + ].

Embodiment 2

[0041] Dissolve 1.96 g (10 mmol) of p-bromonitrile (10 mmol), 1.05 g (8 mmol) of 4-cyanobenzaldehyde and 0.03 g (0.5 mmol) of sodium methoxide in 30 mL of chromatography-grade ethanol. The reaction was stirred at room temperature until a large number of solid particles terminated the reaction. The reaction solution was directly filtered, and the filter cake was recrystallized with absolute ethanol to obtain 2.22 g of brominated stilbene nitrile intermediate represented by formula (V), with a yield of 90%.

Embodiment 3

[0043] Weigh 1.55 g (5 mmol) of the brominated stilbene nitrile intermediate (V) synthesized in Example 1, 1.18 g (6 mmol) of 4,4'-dimethyldiphenylamine, and 2 g of cesium carbonate ( 10 mmol) was dissolved in 25 mL of toluene. Under an inert gas atmosphere, 0.033 g (0.2 mmol) of palladium acetate and 1 mL of tri-tert-butylphosphine were added, and the mixture was heated at 110 °C for 24 h. After the reaction was complete, the reaction solution was extracted with dichloromethane, the organic phase was washed 3 times with saturated brine, dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated under reduced pressure to obtain a crude product, the residue was dissolved in dichloromethane, and the Column separation [dichloromethane: petroleum ether = 1:1~200 (volume ratio)], collecting the dichloromethane-petroleum ether eluate containing the product (I), distilling off the solvent to obtain the yellow solid product (I) 1.49 g, the yield is 70%. Its stru...

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Abstract

The invention discloses a toluylene nitrile derivative with a D-A structure and a synthesis method and application thereof. A structural formula of the toluylene nitrile derivative with the D-A structure is represented by the formula (I) or (II). The toluylene nitrile derivative with the D-A structure can be taken as reversible force to stimulate a fluorescence switch material, and the force stimulation has the characteristics of high contract, automatic recovery and good circulation in response to fluorescence switch performance. The synthesis method is simple; and the toluylene nitrile derivative can be taken as the reversible force to conveniently stimulate devices made of the fluorescence switch material, and can be applied to the fields of fluorescence switches, sensors, storage, display and the like.

Description

(1) Technical field [0001] The present invention relates to a stilbene nitrile derivative with a D-A structure represented by formula (I) or formula (II) and its synthesis method and application, especially the application as a pressure-sensitive material. (2) Background technology [0002] The phenomenon in which the fluorescent color of a material changes when a mechanical force is applied is called piezochromism, and this unique phenomenon makes it a great commercial prospect in the fields of sensing, anti-counterfeiting, storage and display. [0003] After being stimulated by a force, the molecular-molecule interaction force changes, resulting in a change in the packing mode of the molecules, making the molecules change from one ordered structure to another ordered or partially ordered or disordered structure, thus causing The spectrum of the material changes. When it is heated or placed in an organic solvent atmosphere, it returns to the original stacking mode, realizi...

Claims

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Application Information

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IPC IPC(8): C07C255/58C07C253/30C09K9/02
Inventor 欧阳密张诚俞春辉孙璟玮张玉建胡彬
Owner ZHEJIANG UNIV OF TECH
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