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Cyanostilbene derivative, preparation method and application thereof

A technology of stilbene nitrile and derivatives, which is applied in the fields of storage, display, sensor, and anti-counterfeiting, can solve problems such as limiting the application of materials, and achieve the effects of good cycleability, high contrast, and simple synthesis method.

Active Publication Date: 2015-12-02
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] 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), which greatly limits the application of such materials

Method used

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  • Cyanostilbene derivative, preparation method and application thereof
  • Cyanostilbene derivative, preparation method and application thereof
  • Cyanostilbene derivative, preparation method and application thereof

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Effect test

Embodiment 1

[0040] Dissolve 0.92g (5mmol) of p-bromobenzaldehyde (II), 1.73g (6mmol) of triphenylamine (III) 4-boronate, 0.11g (0.1mmol) of tetrakis(triphenylphosphine) palladium in 50mL of toluene / 30mL of tetrahydrofuran and mix To the solution, aqueous sodium carbonate solution (2.0 M, 3 mL) was added. Under a nitrogen atmosphere, the temperature was raised to 90° C. for 36 h. The reaction solution was cooled, and the solvent was evaporated under reduced pressure, then extracted with chloroform (50 mL×3) times, the organic phases were combined, washed with saturated aqueous sodium carbonate solution and 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. The eluent was a mixed solvent with a volume ratio of petroleum ether / chloroform of 150 / 1. The eluate containing the target compound was collected, and the solvent was evaporated under red...

Embodiment 2

[0042] Dissolve 0.92g (5mmol) of p-bromobenzaldehyde (II), 1.56g (4mmol) of triphenylamine (III) 4-boronate, 0.16g (0.15mmol) of tetrakis(triphenylphosphine) palladium in 40mL of toluene / 25mL of tetrahydrofuran and mix To the solution, aqueous sodium carbonate solution (2.0 M, 3 mL) was added. Under a nitrogen atmosphere, the temperature was raised to 90° C. for 24 h. The reaction solution was cooled, and the solvent was evaporated under reduced pressure, then extracted with chloroform solution (30mL×3), the organic phases were combined, washed with saturated aqueous sodium carbonate solution and 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. The eluent was a mixed solvent with a volume ratio of chloroform / petroleum ether of 150 / 1. The eluate containing the target compound was collected, and the solvent was evaporated under ...

Embodiment 3

[0044] Weigh 4.19g (12mmol) of the above-synthesized triphenylamine intermediate (IV), 1.33g (10mmol) of 4-methoxybenzonitrile (V) and 0.06g (1mmol) of sodium methoxide and dissolve them in 30ml of chromatographic ethanol. The reaction was stirred at room temperature for 4 h, and the reaction was terminated when a large amount of solid particles were precipitated. Then the reaction system was put into -20 DEG C refrigerator overnight, then filtered, and the filter cake was rinsed with ethanol (50mL * 3), and after natural drying, an orange powder was obtained, i.e. the target product stilbene nitrile derivative (I) 3.82g, The yield was 80%. The structural confirmation of the substance is characterized as follows: 1 HNMR (500MHz, CDCl3): δ7.93 (d, J = 8.3Hz, 2H); 7.68 (t, J = 16.2Hz, 2H); 7.64-7.61 (m, 2H); 7.52 (d, J = 8.3Hz ,2H); 7.44(s,1H); 7.29(t,J=7.6Hz,4H); 7.10(dd,J=47.4,5.5Hz,8H);6.99-6.95(m,2H);3.86(s, 3H).MSm / z:478.4

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Abstract

The invention provides a cyanostilbene derivative shown as formula (I). The preparation method includes: reacting 4-bromobenzaldehyde shown as formula (II) with 4-(diphenylamino)phenylboronic acid shown as formula (III) to generate a triphenylamine intermediate shown as formula (IV); and then subjecting the triphenylamine intermediate shown as formula (IV) and 4-methoxybenzonitrile shown as formula (V) to Knoevenagel condensation reaction so as to generate the cyanostilbene derivative. The force stimulation responsive fluorescence switch performance of the cyanostilbene derivative has the characteristics of high contrast, self restorability and good cyclicity, the synthesis method is simple, and the cyanostilbene derivative can be applied as a reversible force stimulation fluorescence switch material in fluorescent switch, sensor, storage, display and other fields. (formula (I), formula (II), formula (III), formula (IV) and formula (V)).

Description

(1) Technical field [0001] The invention relates to a stilbene nitrile derivative, a preparation method thereof and an application as a reversible force stimulating fluorescent switch material, which is suitable for sensors, anti-counterfeiting, storage and displays. (2) Background technology [0002] The phenomenon that the fluorescence color changes when the material is subjected to mechanical force is called piezochromism, and substances with piezochromism have at least two stable or metastable accumulation modes affected by pressure. After being stimulated by a force, the internal force of the molecule changes, resulting in a change in the molecular packing method, which makes the material change from one ordered structure to another ordered or partially ordered or disordered structure, and the photophysical properties of the material change with time. change. Then, after being treated with heating and solvents, the accumulation mode of the molecules will return to the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/43C07C253/30C09K9/02
Inventor 张诚占玲玲欧阳密孙璟玮吕晓静
Owner ZHEJIANG UNIV OF TECH
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