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Dianthranide-based compounds as well as preparation method and application thereof as high-pressure transducer

A compound and aryl technology, which is applied in the field of fluorescent compounds and their preparation, can solve problems such as poor measurement, expensive detection instruments, and inconvenient convenience, and achieve the effects of wide detection range, wide practical range, and convenient use

Active Publication Date: 2017-12-15
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its luminous intensity decreases significantly with pressure, and it is difficult to measure at higher pressures; and the luminous band is very narrow, which requires a high-resolution fluorescence instrument to measure
The second category is the luminescence wavelength or luminescence lifetime of some doped metal salts, such as Sm 2+ : MFCl (M = Ba, Sr), Eu 3 + : YAG, Eu 3+ : YAG, etc. However, due to various reasons, they are not as widely used as ruby ​​in terms of calibration pressure
The disadvantage is that the detection instrument is too expensive and not convenient enough

Method used

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  • Dianthranide-based compounds as well as preparation method and application thereof as high-pressure transducer
  • Dianthranide-based compounds as well as preparation method and application thereof as high-pressure transducer
  • Dianthranide-based compounds as well as preparation method and application thereof as high-pressure transducer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Preparation of compound 1, its reaction scheme is as follows:

[0053]

[0054] First add 9-anthrone (5g, 26mmol), zinc powder (8.5g, 129mmol), zinc chloride (7g, 56mmol) into the three-necked flask, then add a certain proportion of tetrahydrofuran and water mixed solvent 100ml, add magnetic After stirring at room temperature for more than 8 hours, extract with dichloromethane, dry with anhydrous magnesium sulfate, filter, spin dry, and obtain 4.8 g of a yellow solid after drying, then add the yellow solid into a three-necked flask, and add a small amount of p-toluenesulfonic acid ( PTS), use toluene as a solvent, reflux until the solvent becomes clear, extract with solvent dichloromethane and dry with desiccant anhydrous magnesium sulfate, filter, spin dry, and obtain 4.3g of white crystalline solid by silica gel column purification , yield 93%.

[0055] Preparation of compound 2, its reaction scheme is as follows:

[0056]

[0057] Dissolve 3g of compound 1 (8...

Embodiment 2

[0062] Compound PAAP is prepared, wherein the reaction scheme is as follows:

[0063]

[0064] Wherein the synthetic method of compound 1 sees embodiment 1

[0065] Preparation of Compound 3: Compound 1 (1g, 2.8mmoL) was added to a three-neck flask, dissolved in 100mL of chloroform solvent, slowly added dropwise to 50mL of a solution containing N-bromosuccinimide (1.2g, 6.8mmoL), and stirred at room temperature 3-8h. It was extracted with dichloromethane as a solvent, dried with anhydrous magnesium sulfate as a desiccant, filtered, spin-dried, and purified with petroleum ether through a silica gel column to obtain 1.35 g of a solid with a yield of 95%.

[0066] Preparation of compound PAAP: Compound 3 (1g, 1.96mmoL) was added to a three-necked flask, vacuumed and replaced with nitrogen three times, dissolved in 100mL of dry and refluxed tetrahydrofuran, bathed in acetone on dry ice, and 3mL of n-butyllithium was slowly added dropwise after about half an hour. After low-te...

Embodiment 3

[0068] Preparation contains the macromolecular film of compound DAAD among the embodiment 1, and preparation method is that compound DAAD and macromolecular material polymethyl methacrylate are dissolved in methylene chloride solution, wherein the mass ratio of compound DAAD and macromolecular material is 1: 200, pour it into a clean petri dish after fully stirring, and put it in a 45°C oven to dry.

[0069] figure 1 For the fluorescence spectrum of the polymer film containing compound DAAD prepared in Example 3 under different pressures, it can be seen from the figure that as the pressure increases, the wavelength of fluorescence emission has been red-shifted from about 572nm to about 677nm, The corresponding fluorescent color changes gradually from green to yellow to orange and finally to deep red.

[0070] figure 2 The linear curve between the maximum fluorescence wavelength and each pressure of the polymer film containing compound DAAD prepared in embodiment 3 under dif...

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Abstract

The invention relates to dianthranide-based compounds as well as a preparation method and an application thereof as a high-pressure transducer. The compounds have molecular inner conformation continuously changing under pressure, have a broad pressure sensing range and can be used for pressure detection in different environments. The detection results of the compounds can be recognized in two modes including a spectral recognition mode and a chromatic recognition mode, and the dianthranide-based compounds can be used for detection by a spectrometer and by naked eyes.

Description

technical field [0001] The invention relates to a fluorescent compound that can be used for pressure sensing and a preparation method thereof, which has a large detection range and can recognize the detection result with the naked eye. Background technique [0002] The bianthracene compound has the characteristics of non-conjugation in molecular structure, this non-conjugated π structure makes it have high research value, when it is connected with the adjacent strong electron-donating system or electron-deficient system , produces a strong delocalization effect, which gives it some remarkable properties, such as intramolecular charge transfer, high luminescence efficiency in solution and solid state. This kind of property makes the dianthracene compounds have optical and electrical properties, and has broad application prospects in the field of optoelectronics, such as being used as photochemical sensors and light-emitting layer materials of organic light-emitting diodes. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/51C07C253/30C07C317/14C07C315/02C07D417/12G01L1/24C09K11/06
CPCC07C255/51C07C317/14C07D417/12C09K11/06C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1037G01L1/24
Inventor 杨国强钱妍檀康明苏磊王双青
Owner INST OF CHEM CHINESE ACAD OF SCI
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