A phenothiazine-containing benzophenone-based luminescent material and its synthesis method and application

A phenothiazine benzophenone, luminescent material technology, applied in luminescent materials, material analysis by optical means, material analysis and other directions, can solve the problems of poor sensitivity, high detection limit, rough detection means, etc., to achieve accurate detection, Easy purification, high fluorescence quantum efficiency effect

Active Publication Date: 2021-02-26
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This kind of detection method is relatively rough, the detection limit is high, and the sensitivity is poor, so it needs to be further improved.

Method used

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  • A phenothiazine-containing benzophenone-based luminescent material and its synthesis method and application
  • A phenothiazine-containing benzophenone-based luminescent material and its synthesis method and application
  • A phenothiazine-containing benzophenone-based luminescent material and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (1) Synthesis of intermediate [4,4-difluorobenzophenone]

[0043]

[0044] Add 4-fluorobenzoyl chloride (5.00g, 31.5mmol) into a 250mL dry three-necked flask, then add fluorobenzene (7.58g, 78.8mmol), stir, add anhydrous aluminum chloride (12.6g, 94.1mmol), Raise the temperature to 40-50°C and react for 5-6 hours. After the reaction, add 50ml of dichloromethane into the three-neck flask to dissolve, slowly add dilute hydrochloric acid, and stir until there is no precipitation. Then the reaction solution was poured into a separatory funnel, extracted 3 times with dichloromethane, and washed 2-3 times with dilute hydrochloric acid until the aqueous layer became colorless. The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was spin-dried in a rotary evaporator to obtain 5.73 g of a white solid. Yield 83.3%.

[0045] (2) Synthesis of intermediate [4-fluoro-4'-phenothiazinylbenzophenone]

[0046]

[0047] Add phenothiazine (1.03 g, ...

Embodiment 2

[0055] (1) synthesis of target product embodiment 2

[0056]

[0057] Referring to step (2) of Example 1, 4-carbazolyl-4'-phenothiazinyl benzophenone was used instead of 4,4-difluorobenzophenone to synthesize 4-carbazolyl-4'-phenothiazinyl diphenone benzophenone. (52.5% yield) 1 H NMR (300MHz, CDCl 3 )δ8.16-8.14(d,2H),8.05-8.03(d,2H),7.92-7.90(d,2H),7.72-7.70(d,2H),7.53-7.26(m,11H),7.25, 7.21-7.10(t,5H).

Embodiment 3

[0059] (1) Synthesis of intermediate [1-bromo-4-phenothiazinylbenzene]

[0060]

[0061] Add phenothiazine (3.00g, 15.1mmol) and 1-bromo-4-iodobenzene (4.68g, 16.6mmol) into a 250mL three-neck flask, add an appropriate amount of DMF to dissolve, add a teaspoon of iodine under stirring with argon gas Cuprous chloride, 18-crown-6 and o-phenanthroline were stirred evenly, and then potassium carbonate (6.51g, 45.3mmol) was added, heated to reflux and stirred for 12h. Cool to room temperature, pour into cold water, extract 3 times with dichloromethane, wash 2 times with water, dry the organic layer with anhydrous sodium sulfate, and spin dry in a rotary evaporator. Then it was purified by silica gel column chromatography, and the eluent was a mixed solution of dichloromethane and n-hexane with a volume ratio of 1:3. 2.54 g of white solid was obtained, with a yield of 47.6%.

[0062] (2) Synthesis of intermediate [4-phenothiazinyl phenyl borate]

[0063]

[0064] Add 1-brom...

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Abstract

The invention discloses a phenothiazine-containing benzophenone-based luminescent material and its synthesis method and application. The sulfur atom on the phenothiazine group contained in the luminescent material itself is easily oxidized by peroxyl radicals or singlet oxygen The formation of sulfoxide or sulfone will lead to a great change in the luminescent properties of the entire molecule, which can be easily recognized by the naked eye. The concentration of peroxide can also be determined through the change of fluorescence spectrum to achieve more accurate detection. The synthesis method of the present invention has simple process and is easy to purify. The synthesized luminescent material has high fluorescence quantum efficiency and has specific response to peroxide free radicals, and phenothiazine groups are easily oxidized and changed by active oxygen free radicals and singlet oxygen. Its luminescent properties are suitable for chemical and biological detection, biological imaging and anti-counterfeiting fields.

Description

technical field [0001] The invention relates to the field of new materials, in particular to a novel organic luminescent material containing phenothiazine groups, a synthesis method thereof, and an application in the field of chemical peroxide detection. Background technique [0002] Organic peroxides refer to liquid or solid organic substances with a divalent -O-O- structure in their chemical structure, including mixtures of organic peroxides. Organic peroxides have high chemical activity, are sensitive to heat, impact or friction, can undergo exothermic self-accelerating explosive decomposition, and are prone to dangerous reactions with other substances. Many organic compounds will produce peroxides during storage. Peroxides contain peroxide radicals (-O-O-), and the bonding force of peroxide bonds is weak, and only a small amount of energy can be broken. Peroxyl is an extremely unstable structure, which is extremely sensitive to external stimuli such as heat, shock, vibr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D279/26C09K11/06C07D417/10C07D279/22G01N21/64
CPCC07D279/22C07D279/26C07D417/10C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1037G01N21/643G01N21/6486
Inventor 于涛谢宗良王乐宇苏彤彤邓皇俊郑挺池振国张艺刘四委许家瑞
Owner SUN YAT SEN UNIV
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