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Tri-dookie boron compound as well as preparation method and application thereof

A compound and heterocyclic group technology, applied in the field of temperature-fluorescence devices, can solve the problems of low spatial resolution, cumbersome data reading, unsuitable miniaturization, etc., achieve high sensitivity, wide response temperature range, and avoid uneven concentration distribution. The effect of even interference

Active Publication Date: 2015-04-29
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are defects such as not suitable for miniaturization, cumbersome data reading, and low spatial resolution.

Method used

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  • Tri-dookie boron compound as well as preparation method and application thereof
  • Tri-dookie boron compound as well as preparation method and application thereof
  • Tri-dookie boron compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation of tris(2,3,5,6-tetramethyl-4-morpholinophenyl)borane (MPB)

[0049] a) Dissolve 13.4 g of durene (compound 1) in 25 ml of chloroform, add 2 equivalents of bromine, react for 2 hours, and wash with water; obtain white solid compound 2 (26.0 g, 90%).

[0050] b) Dissolve 10g of p-dibromotetramethylbenzene (compound 2) in 300ml of degassed ether, protect with argon, cool down to -78°C, add 1.2 equivalents of n-butyllithium and stir, gradually raise the temperature to 0°C, then cool down again to -78°C. Add 0.3 equivalent of boron trifluoride diethyl ether, return to normal temperature and continue to react for 2 hours. After the reaction, it was washed with water, and purified by silica gel column using petroleum ether as developing solvent. Compound 3 (3.3 g, 45%) was obtained as a white solid.

[0051] c) 4.5 equivalents of sodium tert-butoxide (NaOtBu), 50 ml of toluene, 0.09 equivalents of 2,2'-bisdiphenylphosphino-1,1'-binaphthyl (BINAP) and 0.045 eq...

Embodiment 2

[0053] Preparation of 4,4'-(((4-bromo-2,3,5,6-tetramethylphenyl)boron)bis(2,3,5,6-tetramethyl-4,1-benzene))bis Morpholine (BrMPB)

[0054]

[0055] a) Dissolve 13.4 g of durene (compound 1) in 25 ml of chloroform, add 2 equivalents of bromine, react for 2 hours, and wash with water; obtain white solid compound 2 (26.0 g, 90%).

[0056] b) Dissolve 10g of p-dibromotetramethylbenzene (compound 2) in 300ml of degassed ether, protect with argon, cool down to -78°C, add 1.2 equivalents of n-butyllithium and stir, gradually raise the temperature to 0°C, then cool down again to -78°C. Add 0.3 equivalent of boron trifluoride diethyl ether, return to normal temperature and continue to react for 2 hours. After the reaction, it was washed with water, and purified by silica gel column using petroleum ether as developing solvent. Compound 3 (3.3 g, 45%) was obtained as a white solid.

[0057] c) 3 equivalents of sodium tert-butoxide (NaOtBu) in 50 ml of toluene, 0.06 equivalents of ...

Embodiment 3

[0059] Fabrication of MPB's PEG-4000 solid-state polymer temperature-fluorescent device

[0060] Polymer solid-state polymer temperature-fluorescent device with an action range of -20°C to 40°C, the compound used is the tris(2,3,5,6-tetramethyl-4-morpholine benzene) boron (MPB ). The temperature-fluorescence device is obtained through the response of its two fluorescent excited states to the viscosity of the environment, and the viscosity of the PEG4000 polymer changes with the change of the environment temperature.

[0061] (1) The preparation concentration is 1×10 -3 mol / liter carbon dichloride solution of MPB compound;

[0062] (2) Take 1ml of the solution and drop it into 12.7g (room temperature 10cm 3 ) The melted PEG4000 macromolecule is mixed evenly, and the dichloromethane is removed in a vacuum oven, and the temperature is kept above the melting point of PEG4000;

[0063] (3) At this time, the concentration of MPB in PEG4000 polymer is 1×10 -4 mol / cubic decimeter...

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PUM

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Abstract

The invention discloses a tri-dookie boron compound as well as a preparation method and application thereof. The tri-dookie boron compound is as shown in the specification and can be used as a temperature fluorescence device with liquid and solid self-reference in a liquid organic solvent and solid macromolecules. After the compound is mono-dispersed in the liquid organic solvent or specific solid macromolecules, the lighting color and intensity of the system are changed along with temperature, and the total fluorescence sub-efficiency is always relatively high. The fluorescence device is low in cost, high in shape plasticity, high in sensitivity and good in self-reference property.

Description

technical field [0001] The invention belongs to fluorescent devices in the field of analytical chemistry, in particular to temperature-fluorescent devices in liquid phase and solid state. Background technique [0002] Temperature is one of the most important physical parameters. Due to the development of technology and science, irregular, high spatial resolution, and ultra-small thermometers are becoming more and more important. It is useful for studying biological processes in organisms, especially intracellular biological processes; various chemical reaction processes; or large-scale temperature distribution with high spatial resolution. and other studies can provide key data. Traditional temperature measurement is mainly through thermometers that expand with heat and contract with cold, thermocouples and infrared thermometers. But there are defects such as not suitable for miniaturization, cumbersome data reading, and low spatial resolution. Therefore, there is a great...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K9/02G01K11/32
Inventor 杨国强刘玄王双青李沙瑜
Owner INST OF CHEM CHINESE ACAD OF SCI
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