Triarylamine derivative fluorescent probe as well as preparation method and application thereof

A technology of fluorescent probe and triarylamine, which is applied in the field of triarylamine derivative fluorescent probe and its synthesis, and achieves the effects of obvious detection effect, specificity and high yield.

Active Publication Date: 2021-02-09
HARBIN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the application of triarylamine compounds in the molecular design of fluorescent probes.

Method used

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  • Triarylamine derivative fluorescent probe as well as preparation method and application thereof
  • Triarylamine derivative fluorescent probe as well as preparation method and application thereof
  • Triarylamine derivative fluorescent probe as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

specific Embodiment approach 1

[0040] Specific embodiment one: The structural formula of the triarylamine derivative fluorescent probe in this embodiment is as follows:

[0041]

specific Embodiment approach 2

[0042] Specific embodiment two: the synthesis method of triarylamine derivative fluorescent probe is as follows:

[0043] (1): N 2 protection, anhydrous toluene as solvent, under reflux conditions, cesium carbonate, tri-tert-butylphosphine, Pd 2 DBA 3 Under catalysis, N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluorene-2-amine and p-chlorobenzaldehyde undergo a coupling reaction, the organic phase is washed with water, dried, concentrated, and the column Chromatography (PE:EA=10:1) separation gave triarylamine intermediate. The molar ratio of N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine to p-chlorobenzaldehyde is 1:1.

[0044] (2): Under the action of dichloromethane as a solvent and boron trifluoride ether, the triarylamine intermediate reacts with ethanethiol at room temperature, the organic phase is washed with water, dried, concentrated, and subjected to column chromatography (PE:EA=12:1) Get fluorescent probes.

specific Embodiment approach 3

[0045] Specific embodiment three: the difference between this embodiment and specific embodiment two is: the reaction molar ratio of step (2) triarylamine intermediate and ethanethiol is 1:2.5. Others are the same as in the second embodiment.

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Abstract

The invention discloses a triarylamine derivative fluorescent probe as well as a preparation method and application thereof, and relates to a triarylamine derivative fluorescent probe containing a thioacetal structure as well as a synthesis method and application of the probe. The preparation process of the novel triarylamine derivative fluorescent probe comprises the following steps: carrying outcoupling reaction on N-(4-biphenyl)-(9,9-dimethylfluoren-2-yl)amine and p-chlorobenzaldehyde, and carrying out aldehyde thioacetal protection reaction on the obtained product. According to the fluorescent probe, in a capronitrile (ACN) / buffer solution (HEPES) (9 / 1, v / v) solution, Hg<2+> is used for promoting the deprotection effect of thioacetal to cause the fluorescence effect change of a detection system, so that the on-off detection of Hg<2+> is realized. The probe has the advantages of short response time, good ion selectivity, strong interference resistance to other metal ions and the like in the Hg<2+> detection process, meanwhile, the detection limit is as low as 1.57*10<-8> mol / L, and trace detection of Hg<2+> can be realized. The method is applied to Chinese herbal medicine Hg<2+> detection.

Description

technical field [0001] The invention relates to a fluorescent probe of a triarylamine derivative containing a thioacetal structure, a synthesis method and an application thereof. Background technique [0002] With the development of science and technology, metallic mercury and its compounds are widely used in the fields of chemistry, medicine, metallurgy, electrical equipment, cosmetics and so on. However, mercury is one of the most toxic metal elements. It can not only exist stably for a long time in the environment, but also accumulate continuously along the food chain. The mercury element enriched in the human body will damage the human central nervous system, digestive system and kidneys, and also have certain effects on the respiratory system, skin, blood and eyes. Therefore, it is of great significance to develop a highly selective and sensitive mercury ion detection method. [0003] At present, the detection methods of mercury ions mainly include atomic absorption m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/29C07C319/14C09K11/06G01N21/64
CPCC07C323/29C09K11/06G01N21/643C07C2603/18C09K2211/1011C09K2211/1014C09K2211/1007Y02P20/55
Inventor 刘波荆军凯吴绵园由君武文菊喻艳超
Owner HARBIN UNIV OF SCI & TECH
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