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Carborane-based hydrostatic pressure fluorescence sensing material as well as preparation method and application of hydrostatic pressure fluorescent sensing material

A fluorescence sensing and hydrostatic pressure technology, applied in the chemical field, can solve the problems of molecular luminescence intensity reduction, pressure sensor sensitivity reduction, fluorescence quenching, etc., achieve huge application potential, and overcome the effect of mechanofluorescence quenching

Pending Publication Date: 2021-11-12
HUZHOU TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional organic light-emitting materials, under the action of static pressure, the intermolecular interaction force increases, and the π-π interaction is enhanced, which eventually leads to fluorescence quenching
In other words, under the action of hydrostatic pressure, the intensity of molecular luminescence decreases continuously, which reduces the sensitivity of pressure sensing devices.

Method used

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  • Carborane-based hydrostatic pressure fluorescence sensing material as well as preparation method and application of hydrostatic pressure fluorescent sensing material
  • Carborane-based hydrostatic pressure fluorescence sensing material as well as preparation method and application of hydrostatic pressure fluorescent sensing material
  • Carborane-based hydrostatic pressure fluorescence sensing material as well as preparation method and application of hydrostatic pressure fluorescent sensing material

Examples

Experimental program
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Effect test

Embodiment 1

[0028] A method for preparing a pressure fluorescent sensing material based on carborane, comprising the following steps:

[0029] Weigh 0.299g (1mmol) of 4-carborane bromobenzene (I), 0.222g (1mmol) of phenanthrene boric acid (II), 0.091g (0.08mmol) of tetrakistriphenylphosphine palladium and 0.084g (0.8mmol) of sodium carbonate dissolved in 30mL tetrahydrofuran; under the protection of nitrogen atmosphere, heated and stirred at 90°C for 18h; at the same time, combined with thin layer chromatography (TLC) to determine the reaction process, after the reaction was terminated, the reaction system was extracted three times with water and dichloromethane, and then used The eluent of petroleum ether and dichloromethane in a volume ratio of 8:1 was purified by column chromatography to obtain 0.273 g of white powder with a yield of 35%, which was the target product carborane derivative (III).

[0030] The characterization data are as follows: 1H NMR (400MHz, Chloroform-d) δ8.84(d, J=...

Embodiment 2

[0033] A method for preparing a carborane-based pressure fluorescent sensing material, comprising the following steps:

[0034] Weigh 0.299g (1mmol) of 4-carborane bromobenzene (I), 0.267g (1.2mmol) of phenanthrene boric acid (II), 0.091g (0.08mmol) of tetrakistriphenylphosphine palladium and 0.084g (0.8mmol) of sodium carbonate ) was dissolved in 30mL tetrahydrofuran; under the protection of nitrogen atmosphere, heated and stirred at 90°C for 18h; at the same time, combined with thin layer chromatography (TLC) to determine the reaction process, after the reaction was terminated, the reaction system was extracted three times with water and dichloromethane, and then Purified by column chromatography with an eluent of petroleum ether and dichloromethane at 8:1 to obtain 0.288 g of a white powder with a yield of 37%, which is the target product carborane derivative (III).

Embodiment 3

[0036] A method for preparing a carborane-based pressure fluorescent sensing material, comprising the following steps:

[0037] Weigh 0.299g (1mmol) of 4-carborane bromobenzene (I), 0.244g (1.1mmol) of phenanthrene boric acid (II), 0.091g (0.8mmol) of tetrakistriphenylphosphine palladium and 0.084g (0.8mmol) of sodium carbonate ) was dissolved in 40mL of tetrahydrofuran; under the protection of nitrogen atmosphere, heated and stirred at 100°C for 18h; at the same time, combined with thin layer chromatography (TLC) to determine the reaction process, after the reaction was terminated, the reaction system was extracted three times with water and dichloromethane, and then Purified by column chromatography with petroleum ether and dichloromethane 8:1 eluent to obtain 0.280 g of white powder with a yield of 36%, which is the target product carborane derivative (III).

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Abstract

The invention discloses a carborane-based hydrostatic pressure fluorescence sensing material and a preparation method and an application thereof, the molecular formula of the material is C22H24B10, and the material is prepared through Suzuki coupling reaction by taking phenanthroline boric acid and 4-o-carborane bromobenzene as raw materials. The material can be used as a force-induced fluorescence discoloration pressure sensing probe, overcomes the problem of force-induced fluorescence quenching of a traditional material, shows a force-induced fluorescence enhancement property under low pressure, and has huge application potential in a pressure sensing system.

Description

technical field [0001] The invention belongs to the technical field of chemistry, and in particular relates to a carborane-based hydrostatic pressure fluorescence sensing material and a preparation method and application thereof. Background technique [0002] Pressure (force)-induced chromism refers to the phenomenon that the fluorescent color or / and intensity changes reversibly under the action of external mechanical force (friction, shearing, etc.) or hydrostatic pressure. Piezochromic fluorescence (PCF) materials, because their fluorescence can change continuously under pressure, are used in pressure sensing systems (such as deep-sea submersibles and aircraft wind tunnel tests, etc.), optical records, anti-counterfeiting, information display and storage, etc. field has great application potential. [0003] For traditional organic light-emitting materials, the intermolecular interaction force increases under the static pressure, and the π-π interaction is enhanced, which ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/05C09K11/06G01N21/64
CPCC07F5/05C09K11/06G01N21/643C09K2211/1096C09K2211/1007C09K2211/1011G01N2021/6417
Inventor 吕春燕张玉建杨圣晨孙璟玮曹枫
Owner HUZHOU TEACHERS COLLEGE
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