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Photoluminescence material, and preparation method and applications thereof

A technology of reaction solution and compound, applied in the field of photoluminescent materials and their preparation, can solve the problems of difficulty and cost of increasing oxygen content, and achieve the effects of superior performance, low material cost and high sensitivity

Inactive Publication Date: 2019-07-26
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the current fluorescent oxygen sensors change their luminous intensity with the change of oxygen content. This change often requires the help of instruments and cannot be directly distinguished by human eyes, which increases the difficulty and cost of detecting oxygen content.

Method used

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  • Photoluminescence material, and preparation method and applications thereof
  • Photoluminescence material, and preparation method and applications thereof
  • Photoluminescence material, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The synthesis of embodiment 1 intermediate 1a

[0031] Under nitrogen protection, aniline (931mg, 10mmol), benzil (420mg, 2mmol), 4-bromobenzaldehyde (370mg, 2mmol), and ammonium acetate (617mg, 8mmol) were dissolved in acetic acid (20mL) solvent, and the system Reflux for 14 hours. After the system is cooled, add deionized water, a large amount of white solid is precipitated, filter, extract the obtained white solid with dichloromethane and deionized water, combine the organic phase, and add anhydrous MgSO to the obtained organic phase 4 After drying, it was concentrated under reduced pressure, and then separated and purified by column chromatography. The stationary phase was 300-400 mesh silica gel, and the mobile phase was dichloromethane. Finally, 765 mg of the target product was obtained as a white solid with a yield of 85%. 1 H NMR (500MHz, DMSO) δ7.50 (t, J = 7.4Hz, 4H), 7.37–7.22 (m, 14H), 7.19 (t, J = 7.3Hz, 1H). MS (ESI) theoretical value m / z: 451.4, measur...

Embodiment 2

[0032] The synthesis of embodiment 2 compound 1

[0033] Under nitrogen protection, 1a (225mg, 0.5mmol), triphenylamine boronic acid (200mg, 0.54mmol), sodium carbonate (424mg, 4mmol), tetrakistriphenylphosphine palladium (30mg), dissolved in distilled water (2ml) and toluene (3ml) in a mixed solvent, the system was refluxed for 48 hours. After the system was cooled, a small amount of distilled water was added to quench the reaction, the obtained mixed solution was extracted with dichloromethane and deionized water, the organic phases were combined, and anhydrous MgSO was added 4 After drying, it was concentrated under reduced pressure, and then separated and purified by column chromatography. The stationary phase was 300-400 mesh silica gel, and the mobile phase was dichloromethane: petroleum ether = 3:1 mixed solvent. Finally, 369 mg of the target product was obtained as a white solid. The yield was 60%. 1 H NMR (500MHz, DMSO) δ7.58(dd, J=16.2, 8.7Hz, 4H), 7.50(d, J=7.2Hz,...

Embodiment 3

[0034] Embodiment 3 Preparation of compound 1 solid film

[0035] Compound 1 described in Example 1 was configured into a dichloromethane solution, the solution concentration was 5mg / ml, N 2 Under the atmosphere, place a quartz plate on the spin coater, drop 1-3ml of the above solution on the quartz plate, set the spin coating time to 10 seconds, and the speed to 1000 rpm, turn on the switch, and spin coat to form a film.

[0036] Such as figure 2 As shown, under the condition of pure nitrogen, the blue light emission peak of the film material itself is at about 410nm, without changing other test conditions, as the oxygen content in the test environment increases, a new yellow fluorescence peak at 520nm appears and It increases with the increase of oxygen content, which means that we can quantitatively judge the oxygen content of the test environment through the intensity of the yellow fluorescent peak in the test, and, as figure 2It is shown that until the oxygen content ...

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Abstract

The invention discloses a photoluminescence material represented by formula 1, and a preparation method and applications thereof. The preparation method of the photoluminescence material comprises following steps: under nitrogen protection, aniline, benzil, 4- bromobenzaldehyde, and amine acetate are dissolved in acetic acid solvent, reflux reaction is carried out for 14 to 18h so as to obtain a reaction solution A, and then post-treatment is carried out so as to obtain an intermediate represented by formula 1-a; under nitrogen protection, the intermediate represented by formula 1-a, triphenylamine boric acid, sodium carbonate, and tetrakistriphenylphosphine palladium are dissolved in a mixed solvent, reflux reaction is carried out for 36 to 48h so as to obtain a reaction solution B, and post-treatment is carried out to obtain target compound DPA-PIM represented by formula 1. The raw material cost is low; the synthesis method is simple; the novel material high in sensitivity and excellent in performance is provided for preparation of oxygen sensors; under certain conditions, it is possible to determine existing of oxygen only based on observation of fluorescence color change with naked eyes; and the precision is as high as 0.2% (by volume).

Description

[0001] (1) Technical field [0002] The invention relates to the technical field of an oxygen fluorescence detection material, in particular to a photoluminescent material sensitive to oxygen under illumination, a preparation method thereof and an application in oxygen sensing. [0003] (2) Background technology [0004] In recent years, sensors have been used more and more widely in production and life, and the demand for applications has made them develop extremely rapidly. Space exploration, ocean development, national defense construction, industrial and agricultural production, environmental protection, and life sciences are all inseparable from sensors and sensors. sense technology. At present, with the development of information technology, the importance of sensing technology has been paid more and more attention. [0005] Luminescent chemical sensing has attracted much attention due to its high sensitivity and high selectivity. Luminescent chemical sensing refers to ...

Claims

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Application Information

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IPC IPC(8): C07D233/58C09K11/06G01N21/64
CPCC07D233/58C09K11/06C09K2211/1007C09K2211/1044G01N21/643G01N2021/6432
Inventor 张诚俞越李维军王士昭陈见爱
Owner ZHEJIANG UNIV OF TECH
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