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Diazosulfide benzyl cyanide derivative and preparation method and application thereof

A technology of benzothiadiazole phenylacetonitrile and its derivatives, which is applied in the field of benzothiadiazole phenylacetonitrile derivatives and their preparation, achieving the effect of high contrast and obvious color change

Active Publication Date: 2019-04-19
HUZHOU TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, dyes that induce fluorescence enhancement under low pressure conditions (MPa level) are still rare.

Method used

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  • Diazosulfide benzyl cyanide derivative and preparation method and application thereof
  • Diazosulfide benzyl cyanide derivative and preparation method and application thereof
  • Diazosulfide benzyl cyanide derivative and preparation method and application thereof

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preparation example Construction

[0025] The invention discloses a preparation method of a force-induced fluorescence enhancement material, which comprises the following steps:

[0026] Step 1, the synthesis of intermediate (Ⅱ):

[0027] Its synthetic route is as follows:

[0028]

[0029] Weigh 7-bromobenzene-1,2,5-thiadiazole-4-carbaldehyde (Ⅲ), triphenylamine boric acid (Ⅳ), tetrakistriphenylphosphopalladium and potassium carbonate solution and dissolve them in chromatographic toluene and tetrahydrofuran, wherein , The molar ratio of 7-bromobenzene-1,2,5-thiadiazole-4-carbaldehyde (Ⅲ) to triphenylamine boric acid (Ⅳ) is 1:1-1:1.5; 7-bromobenzene-1,2, 5-thiadiazole-4-carboxaldehyde: potassium carbonate: chromatographic toluene: chromatographic tetrahydrofuran is 10mmol: 0.8-1.2mmol: 50-60ml: 30-40ml; under the protection of nitrogen atmosphere, the reaction time is 12-24h under reflux and stirring. The temperature is 80-100°C, and when a large amount of red solid particles are precipitated, the reaction...

Embodiment 1

[0037] Synthesis of intermediate (Ⅱ): Weigh 1.3g (6mmol) of 7-bromobenzene-1,2,5-thiadiazole-4-carbaldehyde (Ⅲ), 1.8g (6.2mmol) of triphenylamine boric acid (Ⅳ), 0.25g (0.22mmol) tetraphenylphosphopalladium and potassium carbonate solution (3M) were dissolved in chromatographic toluene (50ml) and tetrahydrofuran (30ml). When the solid particles are separated out, click on the plate to determine the reaction progress and terminate the reaction. After the reaction, all the crude products were dissolved with dichloromethane, transferred, washed with water, and the organic phase was taken, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation, and the powdered product and the coarse silica gel powder were mixed and loaded into the column 1.8 g of the product intermediate (II) was obtained with a yield of 75%.

[0038] The characterization data are as follows: 1 H NMR (400MHz, CDCl 3 )δ10.62(s,1H),9.32(d,J=7.2Hz,1H),9.04-9.02(m,3H),7.39(t,J=8H...

Embodiment 2

[0042] Synthesis of intermediate (Ⅱ): Weigh 2.11g (10mmol) of 7-bromobenzene-1,2,5-thiadiazole-4-carbaldehyde (Ⅲ), 2.92g (10.1mmol) of triphenylamine boric acid (Ⅳ) ), tetrakistriphenylphosphopalladium 0.25g (0.22mmol) and potassium carbonate solution (3M) were dissolved in chromatographic toluene (50ml) and tetrahydrofuran (30ml), under nitrogen atmosphere protection, reflux stirring reaction time is 20h, wait for When a large amount of red solid particles precipitated, spot the plate to determine the reaction progress and terminate the reaction. After the reaction, all the crude products were dissolved with dichloromethane, transferred, washed with water, and the organic phase was taken, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation, and the powdered product and the coarse silica gel powder were mixed and loaded into the column , using dichloromethane and petroleum ether at a ratio of 1:2 as the eluent for column chromatography to ...

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Abstract

The invention discloses a diazosulfide benzyl cyanide derivative and a preparation method and application thereof. The preparation method for the derivative comprises the following steps that triphenylamine boric acid, diazosulfide and a benzyl cyanide derivative are taken as raw materials and are subjected to Suzuki coupling and Knoevenagel condensation reactions successively to synthesize the target product diazosulfide benzyl cyanide derivative, namely a force-induced fluorescence enhancement material. The color of the material changes under stimulation of lower pressure (the Mpa level), and the material has the advantages that the contrast ratio is high, and fluorescence intensity is improved significantly (the quantum efficiency is improved to 19.3% from 9%), and can be applied to a pressure sensing system.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a benzothiadiazole phenylacetonitrile derivative and a preparation method and application thereof. Background technique [0002] Stimuli-responsive materials are materials whose physical or chemical properties will change correspondingly under the stimulation of external environmental factors (such as light, force, temperature, pH, ionic strength, electric field and magnetic field, etc.). one of the materials. Among them, organic small molecular piezofluorochromic materials can not only be used as sensors, but also widely used in many emerging fields, such as confidential letter paper. Therefore, it is of great significance to develop new fluorescent organic small molecule functional materials. [0003] As a fluorescent sensor, organic small molecule fluorescent materials have the advantages of high sensitivity, good selectivity, short response time, and ...

Claims

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Application Information

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IPC IPC(8): C07D285/14C09K11/06C09K9/02
CPCC09K9/02C09K11/06C07D285/14C09K2211/1051C09K2211/1007Y02E10/549
Inventor 吕春燕曹枫张玉建杨圣晨
Owner HUZHOU TEACHERS COLLEGE
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