Fluorescent compound for detecting automobile brake fluid as well as preparation method and application of fluorescent compound

A technology for fluorescent compounds and automobile braking, applied in the field of fluorescent probe detection, can solve problems such as detection application limitations, and achieve the effects of good visibility, mild conditions, and simple and reliable detection methods.

Pending Publication Date: 2022-07-12
ZHEJIANG UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The fluorescence of traditional fluorescent probe molecules is quenched in the aggregated state, which limits their detection applications at high viscosity.

Method used

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  • Fluorescent compound for detecting automobile brake fluid as well as preparation method and application of fluorescent compound
  • Fluorescent compound for detecting automobile brake fluid as well as preparation method and application of fluorescent compound
  • Fluorescent compound for detecting automobile brake fluid as well as preparation method and application of fluorescent compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Combine 4-(di-p-tolylamino)benzaldehyde (6.02 g, 20 mmol) with (E)-4-(((4'-(cyanomethyl)-[1,1'-diphenyl]-4-yl )methylene)amino)benzonitrile (7.16 g, 26 mmol) was dissolved in 100 mL of acetonitrile, and 3 drops of piperidine were added dropwise. After the feeding was completed, the reaction mixture was stirred at 80°C for 6 hours. After the heating was stopped, the reaction solution was filtered under reduced pressure, and the filter cake was washed with acetonitrile at 0-10°C. The filter cake was collected and recrystallized from acetonitrile. The recrystallized product was filtered, the obtained solid was collected and dried in vacuo to obtain a total of 9.78 g of the product DBPT-3 with a yield of 81%.

[0051] The structural characterization data related to compound DBPT-3 are as follows: 1 H NMR (400MHz, DMSO-d 6 ,δ):8.29(s,1H),8.05-7.98(m,7H),7.91(d,J=8.8,2H),7.87-7.84(m,6H),7.21(d,J=8.4,4H) , 7.06(d, J=8.4, 4H), 6.89(d, J=9.2, 2H), 2.31(s, 6H). H NMR spectru...

Embodiment 2

[0053] Combine (Z)-2-(4-bromophenyl)-3-(4-(di-p-tolylamino)phenyl)acrylonitrile (4.78 g, 10 mmol) with (E)-(4-((((4- Cyanophenyl)imino)methyl)phenyl)boronic acid (2.76g, 11mmol) was dissolved in 100mL of tetrahydrofuran / water mixed (volume ratio 4:1) solution, and 0.067g of palladium acetate was added. After the feeding was completed, the reaction system was deoxygenated, and then the reaction mixture was stirred at 100° C. for 12 hours under a nitrogen atmosphere. After the heating was stopped, the reaction solution was cooled to room temperature and the insolubles were filtered, then an equal volume of water was added and the aqueous phase was extracted with dichloromethane. Combine the organic phases, spin dry, and then perform silica gel column chromatography with dichloromethane:petroleum ether:ethyl acetate=1:6:0.5 to 1:4:1 (volume ratio) as the fluidity, after gradient elution A total of 4.53 g of the product DBPT-3 was obtained with a yield of 75%. The structural cha...

Embodiment 3

[0055] (Z)-3-(4-(Di-p-tolylamino)phenyl)-2-(4'-formyl-[1,1'-diphenyl]-4-yl)acrylonitrile (0.50 g, 1 mmol) and 4-aminobenzonitrile (0.18 g, 1.5 mmol) were dissolved in 50 mL of ethanol, and 3 drops of glacial acetic acid were added dropwise. After the feeding was completed, the reaction mixture was stirred at room temperature for 10 hours. After the reaction is heated, the reaction solution is filtered under reduced pressure, and the filter cake is washed with ethanol at 0-10° C. (the solvent is less volatile at low temperature, and the solubility of the reactant and the product is quite different). The filter cake was collected and recrystallized from ethanol. The recrystallized product was filtered, and the obtained solid was collected and dried in vacuo to obtain a total of 0.54 g of the product DBPT-3, with a yield of 90%. The structural characterization results of the compound DBPT-3 synthesized by this method are the same as those in method 1.

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Abstract

The invention discloses a fluorescent compound for detecting automobile brake fluid, the relative molecular mass of the fluorescent compound is 604.75, the chemical name of the fluorescent compound is 4-(((E)-(4 '-((Z)-1-cyano-2-(4-(di-p-toluene amino) phenyl) vinyl)-[1, 1'-diphenyl]-4-yl) methylene) amino) benzonitrile, and the fluorescent compound can be used for detecting the change of moisture and temperature in the automobile brake fluid. And further detecting the viscosity of the automobile brake fluid. The invention also provides a preparation method of the fluorescent compound. The synthesis process is diversified and can be suitable for different raw material supply conditions; the molecular preparation method is simple, efficient, short in period, mild in condition, small in pollution and high in yield, and the yield is 75-90%. The invention also provides application of the fluorescent compound in detection of automobile brake fluid.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probe detection, and in particular relates to a fluorescent compound for detecting automobile brake fluid and a preparation method and application thereof. Background technique [0002] Brake fluid is the medium that transmits pressure in the hydraulic braking system of motor vehicles, and is an indispensable part of the braking system. The performance of brake fluid directly affects the driving safety of motor vehicles. The water content and viscosity of brake fluid are directly related to the performance of brake fluid. Taking HZY4 type (corresponding to the brake fluid type DOT4 of the US Department of Transportation) as an example, the Chinese standard "Brake Fluid for Motor Vehicles" (GB 12981-2012) stipulates that its kinematic viscosity should not be greater than 1500mm at -40 °C 2 / s, not less than 1.5mm at 100°C 2 / s; Equilibrium reflux boiling point and wet equilibrium reflux boil...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/61C07C253/30C09K11/06G01N21/64
CPCC07C255/61C09K11/06G01N21/643
Inventor 孙海亚陈水鑫陈孟溢曹诺翁晨阳刘志飞杨佳豪金嘉杰牛俊峰路胜利
Owner ZHEJIANG UNIVERSITY OF SCIENCE AND TECHNOLOGY
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