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A calixarene-based 1,3,4-oxadiazole cu 2+ Fluorescent probe and its synthesis method

A fluorescent probe, oxadiazole technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as poor practicability, and achieve the effect of short synthesis route, high sensitivity and excellent stability

Active Publication Date: 2021-07-02
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, Yu's group reported a copolymer based on 1,3,4-oxadiazole groups, which can also fluorescently recognize Cu 2+ , but subject to Ni 2+ , Hg 2+ Interference, poor practicability (C.-Y.Yu, T.-Y.Shih, Synth.Met., 2014, 191, 12-18)

Method used

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  • A calixarene-based 1,3,4-oxadiazole cu <sup>2+</sup> Fluorescent probe and its synthesis method
  • A calixarene-based 1,3,4-oxadiazole cu <sup>2+</sup> Fluorescent probe and its synthesis method
  • A calixarene-based 1,3,4-oxadiazole cu <sup>2+</sup> Fluorescent probe and its synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of intermediate compound 2a

[0027] Add 1a (0.33g, 1.4mmol), benzoyl peroxide (17mg, 70μmol), N-bromosuccinimide (130mg, 0.75mmol), 25mL carbon tetrachloride respectively in a 50mL round bottom flask , stirred, heated to reflux for 2h, then added N-bromosuccinimide (130 mg, 0.75mmol), and continued to heat to reflux for 3h. After cooling, the solvent was distilled off under reduced pressure, 25 mL of dichloromethane was added, the resulting solution was washed with saturated brine and distilled water, and dried over anhydrous magnesium sulfate for 1 hour. Filtration, solvent removal by distillation under reduced pressure, thick product is purified by silica gel column chromatography (eluent: V 乙酸乙酯 :V 石油醚 =1:15), to obtain 2a as a white solid. Yield 85%.

Embodiment 2

[0029] With Ia(R 1 =(CH 3 ) 3 C, R 3 =H) as an example to illustrate the synthesis of fluorescent probe molecule I

[0030] In a 25 mL round bottom flask was added 3a (195 mg, 0.3 mmol), anhydrous Na 2 CO 3 (71mg, 0.7mmol) and 10mL of anhydrous acetone, magnetically stirred, heated to reflux for 1h. After cooling slightly, 2a (190mg, 0.6mmol) was added and heated to reflux for 24h. Cool to room temperature, remove the solvent by distillation under reduced pressure, add 10 mL of water to the residue, extract three times with dichloromethane (3×10 mL), combine the organic phases, wash with saturated brine and distilled water successively, and dry over anhydrous magnesium sulfate for 1 hour . Filtration, solvent removal by distillation under reduced pressure, thick product is purified by silica gel column chromatography (eluent: V 乙酸乙酯 :V 石油醚 = 1:3), to obtain Ia as a white solid. Yield 46%.

[0031] Such as figure 1 Shown, the nuclear magnetic resonance data proton...

Embodiment 3

[0035] The ultraviolet-visible absorption spectra of Ia and dichloromethane / acetonitrile (volume ratio 125:1) solution added with different metal ions were tested. The specific method is to prepare a concentration of 8 × 10 -6 The dichloromethane solution of the Ia of mol / L and the Na that concentration is 0.01mol / L + , K + , Ca 2+ , Mg 2+ , Cd 2+ , Ni 2+ ,Co 2+ , Zn 2+ , Ag + , Mn 2+ , Cu 2+ A solution of perchlorate in acetonitrile. Take 2.5 mL of the dichloromethane solution of Ia and add 20 μL of acetonitrile solutions of different metal ions respectively, and test the ultraviolet-visible spectrum after shaking.

[0036] Such as image 3 Shown, the maximum absorption wavelength of the dichloromethane solution of Ia is 285nm, when adding Cu 2+ Finally, the maximum absorption wavelength of Ia is 290nm, resulting in a red shift phenomenon, and the absorbance also decreases obviously, while adding other ions, the maximum absorption wavelength and absorbance do not...

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Abstract

The present invention relates to a kind of synthetic method of 1,3,4-oxadiazole compound based on calixarene and its performance in selective recognition of Cu 2+ The purposes of its structure as shown in general formula I. The compound on Cu 2+ It has the advantages of specific and selective recognition performance, high sensitivity and no interference from other coexisting ions, and also has the characteristics of simple structure, short synthesis route, and high yield. The compound in aqueous solution and biological cells Cu 2+ It has wide application prospects in the detection and other aspects.

Description

[0001] Technical field The present invention belongs to the technical field of fluorescent probes and preparation thereof, in particular to the synthesis method of 1,3,4-oxadiazole compounds based on calixarene and its ability to selectively recognize Cu 2+ the use of. Background technique [0002] Copper is the third most essential trace element in the body and plays a vital role in a variety of cellular processes and the nervous system. Copper ions are coenzyme factors of many enzymes in organisms and play an important role in various physiological processes. Cu 2+ It is also the main source of heavy metal pollution in the natural environment. With the development of industry, more and more Cu 2+ It enters the environment through the discharge of waste gas, sewage and waste residues, endangering the environment and posing a serious threat to human health. Cu 2+ Too little or too much has an important impact on the natural environment and the internal environment of the h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/107C07D413/14C09K11/06G01N21/64
CPCC07D271/107C07D413/14C09K11/06C09K2211/1029C09K2211/1033G01N21/6428
Inventor 韩杰孙春谢迪欢王彦美
Owner NANKAI UNIV
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