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

A technology of derivatives and grease, applied in the field of silole derivatives with luminescent properties, to achieve the effect of excellent photoluminescence 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

[0047] Add 487mg (1mmol) 1-alkynyl-1,2,3,4,5-pentaphenylsilole, 268mg (1.2mmol) 8-bromooctanoic acid, 19mg (0.1mmol) cuprous iodide to a 100mL Schlenk reaction flask , 26mg (0.1mmol) triphenylphosphine, under the protection of nitrogen, add 23mg (0.02mmol) tetrakistriphenylphosphine palladium, 30mL tetrahydrofuran / triethylamine (2 / 1, v / v), react at room temperature for 48 hours. After the reaction was finished, filter and spin the filtrate to dryness, use dichloromethane / methanol (20 / 1, v / v) mixed solvent as eluent to separate and purify the product by column chromatography to obtain 450 mg of yellow solid product. The rate is 72%. The NMR results of the product are: 1 HNMR (400MHz, CDCl 3 ),δ(TMS,ppm):7.78(m,2H),7.34(m,3H),7.13–6.87(m,20H),2.55(m,2H),2.18(m,2H),1.54(m, 2H),1.42(m,2H),1.32–1.26(m,6H); MS(MALDI-TOF):m / z calcd:628.3[M] + , found: 628.3.

[0048] The reaction formula of embodiment 1 is as follows:

[0049]

Embodiment 2

[0051] Add 425 mg (1 mmol) 1-methyl-1-ynyl-2,3,4,5-tetraphenylsilole, 268 mg (1.2 mmol) 8-bromooctanoic acid, 19 mg (0.1 mmol) iodine to a 100 mL Schlenk reaction flask Cuprous chloride, 26mg (0.1mmol) triphenylphosphine, under nitrogen protection, add 23mg (0.02mmol) tetrakistriphenylphosphine palladium, 30mL tetrahydrofuran / triethylamine (2 / 1, v / v), react at room temperature 48 hours. After the reaction, filter and spin the filtrate to dryness, use dichloromethane / methanol (20 / 1, v / v) mixed solvent as eluent to separate and purify the product by column chromatography to obtain 390 mg of yellow solid product, product The rate is 69%. The NMR results of the product are: 1 H NMR (400MHz, CDCl 3 ), δ(TMS,ppm):7.14–6.85(m,20H),2.56(m,2H),2.22(m,2H),1.55(m,2H),1.38(m,2H),1.33–1.26( m,6H),0.22(s,3H); MS(MALDI-TOF):m / z calcd:566.3[M] + , found: 566.3.

[0052] The reaction formula of embodiment 2 is as follows:

[0053]

Embodiment 3

[0055] 145 grams of PAO10 base oil and 44.39 grams of octadecylamine were mixed and heated to 60°C in a reactor, and 2.5 grams of 1-methyl-1-(9-carboxynonynyl)-2 prepared in Example 2 , Dissolve 3,4,5-tetraphenylsilole in 25 grams of toluene and add to the reaction kettle, mix 145 grams of PAO10 base oil and 20.61 grams of MDI and heat to 60°C, and add it to the reaction kettle after the MDI is completely dissolved , heat up to 80°C for 30 minutes, continue to heat up to 210°C, then add 145 grams of PAO10 base oil and cool to about 100°C, add 10g of molybdenum dibutyldithiocarbamate to grind into fat.

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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 structure of the silole derivative is represented by a general formula (I), and each group in the general formula (I) is defined in the specification. The lubricating grease provided by the invention has excellent photoluminescence property and excellent antirust property, 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. In recent years, studies have found that some compounds show opposite properties to traditional organic light-emitting compounds. Not only do they have no aggregation fluorescence quenching effect, but i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C09K11/06C10M169/00C10M177/00C10N50/10
CPCC09K11/06C10M169/00C10M177/00C09K2211/1007C09K2211/1096C10M2205/0206C10M2217/0456C10M2227/04C10M2219/068
Inventor 刘欣阳何懿峰魏克成李茂森刘显秋郑会孙洪伟庄敏阳刘伟李朝宇
Owner CHINA PETROLEUM & CHEM CORP
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