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Fluorescent probe containing tetrasthenylvinyl group and synthesis method and application thereof

A technology of fluorescent probes and tetraphenylethylene, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and the preparation of organic compounds. The method is simple, easy to modify, and the effect of mild reaction conditions

Inactive Publication Date: 2017-03-15
JIANGSU POLICE INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, one of the latest latent fingerprint visualization methods is to use substances with aggregation-induced luminescence to visualize latent fingerprints. The four probes reported above for latent fingerprint visualization are all compounds that have been publicly reported before and have no substitutions. The base tetraphenylethylene is not easy to modify, so it cannot further improve the display effect of latent fingerprints

Method used

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  • Fluorescent probe containing tetrasthenylvinyl group and synthesis method and application thereof
  • Fluorescent probe containing tetrasthenylvinyl group and synthesis method and application thereof
  • Fluorescent probe containing tetrasthenylvinyl group and synthesis method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0034] as attached figure 1 And attached figure 2 A fluorescent probe containing a tetraphenylethylene group as shown has a carbon-carbon double bond at the molecular end of the fluorescent probe, and the fluorescent probe comprises the following preparation steps:

[0035] (1) Under the conditions of nitrogen atmosphere and 0°C, 22 mmol of TiCl 4 Add dropwise to the tetrahydrofuran suspension solution containing 44 mmol of zinc powder, and stir at room temperature for 0.5 h; after refluxing for 2.5 h, cool down to 0°C to obtain a mixed solution;

[0036] (2) Dissolve 12mmol of benzophenone and 10mmol of 4'-hydroxyl-benzophenone in dry tetrahydrofuran, and add dropwise to the mixed solution prepared in step (1); reflux, TLC tracking reaction process;

[0037] (3) until the reaction in step (2) is completed, add water to quench the reaction, and the water layer is washed with CH 2 Cl 2 Extracted three times; the organic layer was taken and dried with anhydrous sodium sulf...

Embodiment 2

[0041] as attached figure 1 And attached figure 2 A fluorescent probe containing a tetraphenylethylene group as shown has a carbon-carbon double bond at the molecular end of the fluorescent probe, and the fluorescent probe comprises the following preparation steps:

[0042] (1) Under the conditions of nitrogen atmosphere and 0°C, 11 mmol of TiCl 4 Add dropwise to the tetrahydrofuran suspension solution containing 22mmol of zinc powder, and stir at room temperature for 0.5h; after refluxing for 2.5h, cool down to 0°C to obtain a mixed solution;

[0043] (2) Dissolve 6 mmol of benzophenone and 5 mmol of 4'-hydroxy-benzophenone in dry tetrahydrofuran, and add dropwise to the mixed solution prepared in step (1); reflux, TLC tracking reaction process;

[0044] (3) until the reaction in step (2) is completed, add water to quench the reaction, and the water layer is washed with CH 2 Cl 2 Extracted three times; the organic layer was taken and dried with anhydrous sodium sulfate,...

Embodiment 3

[0048] as attached figure 1 And attached figure 2 A fluorescent probe containing a tetraphenylethylene group as shown has a carbon-carbon double bond at the molecular end of the fluorescent probe, and the fluorescent probe comprises the following preparation steps:

[0049] (1) Under the conditions of nitrogen atmosphere and 0°C, 44 mmol of TiCl 4 Add dropwise to the tetrahydrofuran suspension solution containing 88 mmol of zinc powder, and stir at room temperature for 0.5 h; after refluxing for 2.5 h, cool down to 0°C to obtain a mixed solution;

[0050] (2) Dissolve 24mmol of benzophenone and 20mmol of 4'-hydroxyl-benzophenone in dry tetrahydrofuran, and add dropwise to the mixed solution prepared in step (1); reflux, TLC tracking reaction process;

[0051] (3) until the reaction in step (2) is completed, add water to quench the reaction, and the water layer is washed with CH 2 Cl 2 Extracted three times; the organic layer was taken and dried with anhydrous sodium sulf...

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Abstract

The invention discloses a fluorescent probe containing tetrasthenylvinyl group and a synthesis method thereof, belonging to the technical field of fluorescent probe synthesis. The preparation method comprises the following steps: (1) adding TiCl4 to tetrahydrofuran suspension containing zinc powder, stirring, refluxing and cooling to obtain mixed solution; (2) dissolving benzophenone and 4-hydroxy-benzophenone in tetrahydrofuran and adding dropwise to the mixed solution prepared in step (1); refluxing; until the reaction is complete, quenching with water and extracting the aqueous layer with CH2Cl2; drying the organic layer, drying with anhydrous sodium sulfate, and obtaining white solid by column chromatography; (3) dissolving the white solid synthesized in step (2), 4-chloromethylstyrene and potassium carbonate in acetonitrile solvent, heating and stirring; after completion of the reaction, filtering to obtain filtrate, drying and obtaining the white solid by column chromatography. The fluorescent probe is mild in reaction conditions of the synthesis method and easy to be purified, and high in synthesis yield. In addition the fluorescent probe contains carbon-carbon double bond at the molecular tail, and is easy to modify afterwards.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probe synthesis, and in particular relates to a fluorescent probe containing a tetraphenylethylene group and a synthesis method thereof. Background technique [0002] Fingerprints are widely used as the first piece of evidence in modern forensic science, and they are a tool to identify people who will never make mistakes in the detection of criminal cases. Their unique properties constitute the uniqueness of fingerprints. Conventional methods such as 502 fumigation, iodine fumigation, gold powder and silver powder brushing are sometimes difficult to obtain satisfactory results, and these traditional methods have a great negative impact on the health and environment of professional technicians, and the cost of use is also high . [0003] Since the French doctor Aubert created the fingerprint display technology in 1877, the latent fingerprint display has made great progress. It is not only rely...

Claims

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Application Information

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IPC IPC(8): C07C43/215C07C41/16C07C39/205C07C37/20C09K11/06G01N21/64
CPCC07C43/215C07C37/20C07C41/16C09K11/06C09K2211/1007C09K2211/1014G01N21/6428C07C39/205
Inventor 徐同祥刘景宁金晓东
Owner JIANGSU POLICE INST
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