Pyrazoline derivative Zn<2+> fluorescence probe and its application

A fluorescent probe, pyrazoline technology, applied in the field of organic small molecule fluorescent probes, achieves high sensitivity, great application prospects, and low detection limit

Inactive Publication Date: 2011-11-02
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the search results showed that 5-phenyl-3-(2-hydroxy-4-chloro)phenyl-1-(2-pyridine)pyrazoline as Zn 2+ The application of fluorescent probes has not been reported

Method used

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  • Pyrazoline derivative Zn&lt;2+&gt; fluorescence probe and its application
  • Pyrazoline derivative Zn&lt;2+&gt; fluorescence probe and its application
  • Pyrazoline derivative Zn&lt;2+&gt; fluorescence probe and its application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: the synthetic scheme of formula (1) compound is shown in the following formula:

[0018]

[0019] Concrete synthetic steps are as follows:

[0020] Add 0.131g 2-hydrazinopyridine 3 (12mmol) and 0.12g NaOH (3.0mmol) to a 50mL round bottom flask containing 0.258g chalcone 2 (1.0mmol) and 15mL ethanol, and heat the mixed solution to reflux (about 78°C ) to react for 4h. After the TLC detection reaction was completed, cool to room temperature, add 10mL of cold water, adjust the solution to neutral with dilute hydrochloric acid, and a large amount of solids precipitated out, filtered under reduced pressure, washed the filter cake with water and ethanol, and recrystallized with ethanol to obtain 0.15g of a yellow solid. The yield was 36.0%.

[0021] Melting point determination: mp: 172-173°C;

[0022] Infrared Spectrometry: IR(KBr, cm -1 ): 3066.0, 3031.5, 1588.9, 1476.0, 1443.9, 1255.9, 1145.2, 760.4, 692.9;

[0023] H NMR spectrum determination: 1 H N...

Embodiment 2

[0026] In formula (1) compound (10 -5 M) in the HEPES (pH=7.2) buffer solution of acetonitrile / water (v / v=1 / 1), respectively add 1.0 equivalent of Ag + , Mg 2+ , Hg 2+ , Fe 3+ , Cd 2+ ,Co 2+ , Cu 2+ , Ni 2+ and Zn 2+ Afterwards, measure the intensity change of its fluorescence emission spectrum and find that: formula (1) compound is to Zn 2+ Has a unique fluorescence selectivity, adding 1.0 equivalent of Zn 2+ Afterwards, the fluorescence intensity of the compound of formula (1) at 460nm is enhanced by about 1.8 times, and its fluorescence quantum yield is increased by about 3.5 times, such as figure 1 shown.

Embodiment 3

[0028] In containing formula (1) compound (10 -5 M) and 1.0 equivalent of Zn 2+ Add 1.0 equivalent of Ag to the HEPES (pH=7.2) buffer solution of acetonitrile / water (v / v=1 / 1) + , Fe 3+ ,Co 2+ , Ni 2+ , Cu 2+ , Cd 2+ , Hg 2+ and 50 equivalents of Mg 2+ , Ca 2+ , K+ , Na + Afterwards, measure the intensity change of its fluorescence emission spectrum and find that: formula (1) compound is to Zn 2+ The fluorescent selection has strong anti-interference ability to other metal ions, such as image 3 shown.

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Abstract

The invention discloses a pyrazoline derivative Zn<2+> fluorescence probe, which is 5-phenyl-3-(2-hydroxy-4-chlorine)phenyl-1-(2-pyridine)pyrazoline and has a chemical structural formula as shown in formula (1). In an HEPES (pHH=7.2) buffer solution of acetonitrile / water (v / v=1 / 1), the fluorescence probe provided by the invention has unique fluorescence selectivity, high sensitivity and low detection limit (0.12 micron) for Zn<2+> and strong anti-interference capability against other ions, and has a huge application prospect.

Description

technical field [0001] The present invention relates to a kind of pyrazoline derivative class Zn 2+ Fluorescent probe and application thereof, especially relate to a kind of Zn 2+ A fluorescent probe 5-phenyl-3-(2-hydroxyl-4-chloro)phenyl-1-(2-pyridine)pyrazoline and an application thereof belong to the field of small organic molecule fluorescent probes. Background technique [0002] Due to their good blue light emission, high quantum yield and hole transport efficiency, pyrazoline derivatives are often used in the research of fluorescent probes or chemical sensors for detecting metal ions after structural modification. [0003] Zn 2+ As an important and essential trace element, it is widely distributed in human cells and body fluids, with the highest content in brain cells. Zn 2+ It plays an important role in many physiological processes in the human body, such as DNA synthesis, gene expression, transmission and regulation of nerve signals, cell apoptosis, enzyme cataly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D401/04G01N21/64G01N33/52
Inventor 赵宝祥龚忠亮
Owner SHANDONG UNIV
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