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Triarylphosphine oxide, preparation method thereof and application

A technology of triaryl phosphorus and oxygen compounds, which is applied in the field of triaryl phosphorus oxides and their preparation, can solve the problems of low fluorescence quantum yield, small detection range, and high production cost, and achieve simple synthesis, good stability, and high decomposition The effect of temperature

Active Publication Date: 2017-06-30
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

[0005] Aiming at the problems of small detection range, high production cost, poor stability, and low fluorescence quantum yield at high temperature in current fluorescent temperature probes, the present invention provides a new organic fluorescent material, namely triarylphosphorus oxide, And its preparation method and application

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  • Triarylphosphine oxide, preparation method thereof and application
  • Triarylphosphine oxide, preparation method thereof and application
  • Triarylphosphine oxide, preparation method thereof and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of diphenyl(1'-pyrene)phosphorus oxide

[0038] Experimental steps:

[0039] (1) Under the protection of nitrogen, 1-bromopyrene (2g, 7.6mmol, 1equiv) was dissolved in dry ether, cooled in a dry ice acetone bath (-78°C), and n-butyllithium (5ml, 7.6mmol, 1equiv), after stirring for 2 hours, remove the dry ice acetone bath and heat up to normal temperature and react for 1 hour.

[0040] (2) After the reaction was completed, diphenylphosphorous chloride (1.71 g, 7.6 mmol, 1 equiv) was added dropwise to the reaction system, and the reaction was continued for 8 hours under nitrogen protection. After the reaction, the organic phase was extracted, combined and concentrated to dryness to obtain a solid.

[0041] (3) The obtained solid was dissolved in dichloromethane, and hydrogen peroxide (H 2 o 2 ) (0.17g, 15.2mmol, 2equiv), stirred for 3 hours. After the reaction, the organic phase was extracted, combined and concentrated, and separated and purified by a ch...

Embodiment 2

[0043] Preparation of diphenyl(1'-pyrene)phosphorus oxide

[0044] Experimental steps:

[0045] (1) Under the protection of nitrogen, 1-bromopyrene (2g, 7.6mmol, 1equiv) was dissolved in dry ether, cooled in a dry ice acetone bath (-78°C), and n-butyllithium (6ml, 9.1mmol, 1.2equiv), after stirring for 2 hours, the dry ice acetone bath was removed and the temperature was raised to normal temperature for reaction for 1 hour.

[0046] (2) After the reaction, diphenylphosphorus chloride (1.14 g, 5.1 mmol, 0.67 equiv) was added dropwise to the reaction system, and the reaction was continued for 6 hours under nitrogen protection. After the reaction, the organic phase was extracted, combined and concentrated to dryness to obtain a solid.

[0047] (3) The obtained solid was dissolved in dichloromethane, and hydrogen peroxide (H 2 o 2 ) (0.17g, 15.2mmol, 2equiv), stirred for 3 hours. After the reaction, the organic phase was extracted, combined and concentrated, and separated and...

Embodiment 3

[0049] Preparation of phenylbis(1'-pyrene)phosphorus oxide

[0050] Experimental steps:

[0051] (1) Under the protection of nitrogen, 1-bromopyrene (1g, 3.8mmol, 2equiv) was dissolved in dry ether, cooled in a dry ice acetone bath (-78°C), and n-butyllithium (2.5ml , 3.8mmol, 2equiv), after stirring for 2 hours, the dry ice acetone bath was removed and the temperature was raised to normal temperature to react for 1 hour.

[0052] (2) After the reaction was completed, phenylphosphorus dichloride (0.34 g, 1.9 mmol, 1 equiv) was added dropwise to the reaction system, and the reaction was continued for 8 hours under nitrogen protection. After the reaction, the organic phase was extracted, combined and concentrated to dryness to obtain a solid.

[0053] (3) The obtained solid was dissolved in dichloromethane, and hydrogen peroxide (H 2 o 2 ) (0.043g, 3.8mmol, 2equiv), stirred for 5 hours. After the reaction, the organic phase was extracted, combined and concentrated, and sepa...

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Abstract

The invention relates to a phosphoric-oxygenic compound with a three coordination group and a preparation method thereof. The phosphoric-oxygenic compound is applied to organic fluorescent probes and photoelectric display field. The structure general formula of the phosphoric-oxygenic compound is Ph3-nRnPo, wherein R is an electron-donating group containing an aromatic hydrocarbon conjugated unit. The preparation method is simple in separation and purification operation and high in yield. The formed compound has high decomposition temperature and good heat stability, and can be properly applied to organic fluorescent temperature probes and photoelectric display field.

Description

technical field [0001] The invention belongs to the field of organic fluorescent probes, in particular to a triaryl phosphorus oxy compound and a preparation method thereof, which are applied in the fields of organic fluorescent probes and photoelectric displays. Background technique [0002] Temperature is one of the most basic physical parameters, and temperature sensors are widely used in daily life and scientific research, such as: gas mechanics, climate and ocean research, chemical process, medicine and biology, etc. The application limitations of traditional mechanical or electronic temperature sensors have prompted the development of optical temperature sensors, which can be measured in large areas or in fluid samples or even cells. Among the existing optical methods, the infrared temperature sensor using the principle of black body radiation is characterized by flexibility and ease of use, but it can only measure the temperature of the object surface, thus limiting i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/53C09K11/06G01N21/64H01L51/00H10K99/00
CPCG01N21/6428C09K11/06C07F9/5325C09K2211/1011C09K2211/1007H10K85/622
Inventor 杨国强钱妍方启运
Owner INST OF CHEM CHINESE ACAD OF SCI