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Silole derivative, preparation method and applications thereof, and photoluminescence lubricating grease

A technology of derivatives and lubricating grease, applied in the field of silole derivatives with luminescent properties

Active Publication Date: 2020-04-28
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few reports about luminescent grease

Method used

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  • Silole derivative, preparation method and applications thereof, and photoluminescence lubricating grease
  • Silole derivative, preparation method and applications thereof, and photoluminescence lubricating grease
  • Silole derivative, preparation method and applications thereof, and photoluminescence lubricating grease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Add 487mg (1mmol) 1-alkynyl-1,2,3,4,5-pentaphenylsilole, 264mg (1.2mmol) p-iodophenol, 19mg (0.1mmol) cuprous iodide in 100mL Schlenk reaction bottle, 26mg (0.1mmol) triphenylphosphine, 23mg (0.02mmol) tetrakistriphenylphosphine palladium was added under nitrogen protection, 30mL tetrahydrofuran / triethylamine (2 / 1, v / v), reacted at room temperature for 48 hours. After the reaction, filter and spin the filtrate to dryness, use dichloromethane / petroleum ether (1 / 1, v / v) mixed solvent as eluent to separate and purify the product by column chromatography to obtain 430 mg of yellow solid product, The yield was 74%. The NMR results of the product are: 1 HNMR (400MHz, CDCl 3 ), δ(TMS,ppm):7.74(m,2H),7.36(m,3H),7.15–6.85(m,24H); MS(MALDI-TOF):m / zcalcd:578.2[M] + , found: 578.2.

[0054] The reaction formula of embodiment 1 is as follows:

[0055]

Embodiment 2

[0057] Add 1158mg (2mmol) 1-(4-hydroxyphenynyl)-1,2,3,4,5-pentaphenylsilole, 178mg (1mmol) thiodipropionic acid, 630mg (2.4 mmol) triphenylphosphine, 30 mL tetrahydrofuran, 418 mg (2.4 mmol) diethyl azodicarboxylate was slowly added dropwise at 0° C., and then reacted at room temperature for 18 hours. After the reaction, filter and spin the filtrate to dryness, use dichloromethane / petroleum ether (1 / 2, v / v) mixed solvent as eluent to separate and purify the product by column chromatography to obtain 960 mg of yellow solid product, The yield was 78%. The NMR results of the product are: 1 H NMR (400MHz, CDCl 3 ), δ(TMS,ppm):7.72(m,4H),7.35(m,6H),7.13–6.85(m,48H),2.92(m,4H),2.78(m,4H); MS(MALDI- TOF):m / zcalcd:1298.4[M] + , found: 1298.4.

[0058] The reaction formula of embodiment 2 is as follows:

[0059]

Embodiment 3

[0061]In a 100mL Schlenk reaction flask, add 425mg (1mmol) 1-methyl-1-ynyl-2,3,4,5-tetraphenylsilole, 264mg (1.2mmol) p-iodophenol, 19mg (0.1mmol) iodide Cuprous, 26mg (0.1mmol) triphenylphosphine, under nitrogen protection, add 23mg (0.02mmol) tetrakistriphenylphosphine palladium, 30mL tetrahydrofuran / triethylamine (2 / 1, v / v), react at room temperature for 48 Hour. After the reaction, filter and spin the filtrate to dryness, use dichloromethane / petroleum ether (1 / 1, v / v) mixed solvent as eluent to separate and purify the product by column chromatography to obtain 400 mg of yellow solid product, The yield was 78%. The NMR results of the product are: 1 H NMR (400MHz, CDCl 3 ), δ(TMS,ppm):7.15–6.85(m,24H),0.22(s,3H); MS(MALDI-TOF):m / z calcd:516.2[M] + , found: 516.2.

[0062] The reaction formula of embodiment 3 is as follows:

[0063]

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PUM

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Abstract

The invention provides a silole derivative, a preparation method and applications thereof, and photoluminescence lubricating grease containing the silole derivative, wherein the silole derivative disclosed by the invention has a structure represented by a general formula (I), and each group in the general formula (I) is defined in the specification. The lubricating grease disclosed by the invention has excellent photoluminescence property and excellent oxidation resistance, and can be applied to related mechanical equipment in the electric appliance industry, the metallurgical industry, the food industry, the papermaking industry, the automobile industry and the airplane industry.

Description

technical field [0001] The present invention relates to a silole derivative, in particular to a silole derivative with light-emitting properties. Background technique [0002] Traditional organic chromophores usually have strong luminescence at low concentrations, but weak or even no luminescence at high concentrations or in the solid state, showing an aggregation fluorescence quenching effect. This is due to the fact that in the aggregated state, the strong interaction between molecules leads to an enhanced non-radiative decay process of the excited state, and a significant decrease in the fluorescence quantum yield. In the actual application process, the aggregation fluorescence quenching effect largely limits the practical application of organic light-emitting materials. Studies in recent years have found that some compounds show opposite properties to traditional organic light-emitting compounds, not only have no aggregation fluorescence quenching effect, but show aggre...

Claims

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Application Information

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IPC IPC(8): C07F7/08C09K11/06C10M169/00C10M177/00C10N50/10C10N30/10
CPCC09K11/06C10M169/00C10M177/00C09K2211/1007C10M2205/0206C10M2217/0456C10M2227/04Y02E60/10
Inventor 刘欣阳庄敏阳刘显秋魏克成孙洪伟何懿峰李茂森郑会刘伟李朝宇
Owner CHINA PETROLEUM & CHEM CORP
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