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Room temperature phosphorescence molecule based on phenothiazine derivative, preparation method and application thereof

A phenothiazine derivative and room temperature phosphorescence technology, which is applied in the application of anti-counterfeiting materials, room temperature phosphorescence molecules and their preparation fields, can solve the problems of scarcity and few types of pure organic room temperature phosphorescence materials, and achieves high yield and mild reaction conditions. Effect

Active Publication Date: 2019-01-15
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are very few types of pure organic phosphorescent materials reported so far, especially long-lived pure organic room-temperature phosphorescent materials are very scarce. Therefore, how to develop long-lived pure organic room-temperature phosphorescent materials has become the focus and difficulty of research in this field.

Method used

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  • Room temperature phosphorescence molecule based on phenothiazine derivative, preparation method and application thereof
  • Room temperature phosphorescence molecule based on phenothiazine derivative, preparation method and application thereof
  • Room temperature phosphorescence molecule based on phenothiazine derivative, preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0029] Example 1: Compound CS-CH 3 Synthesis of O

[0030] Under nitrogen protection, in a reaction flask, phenothiazine (1.99g, 10mmol), 4-methoxyiodobenzene (2.34g, 12mol), potassium tert-butoxide (1.68g, 15mmol) and palladium acetate (0.11 g, 0.5mmol), tri-tert-butylphosphine (0.5mL, 0.25mmol) were dissolved in a sufficient amount of toluene solution, stirred and refluxed at 110-120°C for 12h, after the reaction was completed, the reaction solution was cooled to room temperature, and then used Extract with chloroform, collect the organic phase, and then use anhydrous Na 2 SO 4 Dried and spin-dried to obtain a crude product. Using petroleum ether as eluent, the crude product was separated and purified by silica gel column chromatography, and then the obtained product was dissolved in a mixed solution of dichloromethane (90 mL), acetic acid (45 mL) and hydrogen peroxide (2 mL), and dissolved at 70 ℃ for 12 h, the reaction solution was extracted with chloroform, the organi...

Embodiment 2

[0033] Example 2: Compound CS-CH 3 Synthesis

[0034] Under nitrogen protection, in a reaction flask, phenothiazine (1.99g, 10mmol), 4-methyliodobenzene (2.62g, 12mol), potassium tert-butoxide (1.68g, 15mmol) and palladium acetate (0.11g , 0.5mmol), tri-tert-butylphosphine (0.5mL, 0.25mmol) were dissolved in a sufficient amount of toluene solution, stirred and refluxed at 110-120°C for 15h, after the reaction was completed, the reaction solution was cooled to room temperature, and then used three Extract with methyl chloride, collect the organic phase, and then use anhydrous Na 2 SO 4 Dried and spin-dried to obtain a crude product. Using petroleum ether as eluent, the crude product was separated and purified by silica gel column chromatography, and then the obtained product was dissolved in a mixed solution of dichloromethane (90 mL), acetic acid (45 mL) and hydrogen peroxide (2 mL), and dissolved at 70 ℃ for 16 h, the reaction solution was extracted with chloroform, the o...

Embodiment 3

[0037] Embodiment 3: the synthesis of compound CS-H

[0038] Under nitrogen protection, in a reaction flask, phenothiazine (1.99g, 10mmol), iodobenzene (2.45g, 12mol), potassium tert-butoxide (1.68g, 15mmol) and palladium acetate (0.11g, 0.5mmol) , Tri-tert-butylphosphine (0.5mL, 0.25mmol) was dissolved in a sufficient amount of toluene solution, stirred and refluxed at 110-120°C for 20h, after the reaction was completed, the reaction solution was cooled to room temperature, and then extracted with chloroform, The organic phase was collected and washed with anhydrous Na 2 SO 4 Dried and spin-dried to obtain a crude product. Using petroleum ether as eluent, the crude product was separated and purified by silica gel column chromatography, and then the obtained product was dissolved in a mixed solution of dichloromethane (90 mL), acetic acid (45 mL) and hydrogen peroxide (2 mL), and dissolved at 70 ℃ for 18 h, the reaction solution was extracted with chloroform, the organic ph...

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Abstract

The invention discloses a room temperature phosphorescence molecule based on a phenothiazine derivative, a preparation method and application thereof. The room temperature phosphorescence molecule based on the phenothiazine derivative has a structure shown as formula (I), wherein R is -OCH3, -CH3, -H, -Br, -Cl, -F or -CF3. According to the invention, mainly phenothiazine is adopted as the core, and C-N coupling reaction is carried out to connect phenothiazine with a benzene ring derivative, and then oxidation is carried out to obtain the target product. The solid powder of the compounds all have room temperature phosphorescence phenomenon, and have a longest life up to 398ms, thus being applicable as anti-counterfeit materials. And the preparation method provided by the invention has the advantages of mild reaction conditions and high yield.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and specifically relates to a class of room-temperature phosphorescent molecules based on phenothiazine derivatives, a preparation method thereof and an application as an anti-counterfeit material. Background technique [0002] Phosphorescent materials have broad application prospects in many high-tech fields such as anti-counterfeiting, biological imaging, molecular sensing, photocatalytic reactions, and photovoltaic devices. Traditional room-temperature phosphorescent materials are mostly inorganic compounds and organic metals, but inorganic compounds and organic metals have many disadvantages, such as limited varieties, high material costs, easy damage, unsuitable for large-scale preparation, and poor stability. Pure organic molecular phosphorescent materials are relatively cheap, easy to adjust the structure, relatively safe to the environment and have good processability, which makes them mo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/34C09K11/06
CPCB42D25/36C07D279/34C09K11/06C09K2211/1007C09K2211/1037
Inventor 李振杨杰
Owner WUHAN UNIV
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