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A kind of coumarin-thiacalix[4]arene fluorescent reagent and its preparation method and application

A kind of aromatic hydrocarbon fluorescence, thia calix technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as poisoning, damage to the immune system, etc.

Inactive Publication Date: 2015-08-26
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, excess fluoride ions lead to diseases such as fluorosis, suppression of thyroid activity, bone disease and damage to the immune system

Method used

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  • A kind of coumarin-thiacalix[4]arene fluorescent reagent and its preparation method and application
  • A kind of coumarin-thiacalix[4]arene fluorescent reagent and its preparation method and application
  • A kind of coumarin-thiacalix[4]arene fluorescent reagent and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] (1) Synthesis of intermediate raw material 1,3-alternate-bis(phthalimidoethoxy)thiacalix[4]

[0087] N 2 protection, in a 50mL round bottom flask, add thiacalix[4] (721mg, 1.00mmol), N-hydroxyethylphthalimide (1.75g, 8.57mmol), triphenylphosphine (800mg , 3.05mmol), dry tetrahydrofuran 20 mL, under ice bath, then slowly add diethyl azodicarboxylate (531mg, 3.05mmol) dropwise, after the addition, stir the reaction at room temperature for 48h, evaporate the solvent, add hot methanol while hot 20mL was cooled, and a large amount of white solid crude product was precipitated. The crude product was separated by column chromatography (elution machine: ethyl acetate: n-hexane V:V=1:4) to obtain 748 mg of white product, with a yield of 70%. m.p. 288~290℃; 1 H NMR (CDCl 3 , 400 MHz), δ(ppm): 0.738[ s, 9H, C(CH 3 ) 3 ], 1.284[s,9H, C(CH 3 ) 3 ], 4.457(t,2H,J=5.5 Hz, NCH 2 ), 4.880(t,2H,J=6.0Hz,OCH 2 ), 6.828(s,2H,ArH), 7.264(d,2H,J=7.5Hz, OH), 7.487(s,2H, ArH), 7.560~7.5...

Embodiment 2

[0098] Add the acetonitrile stock solution of the probe compound (1.00×10 -4 mol L -1 , 1mL), anion F - (2.00×10 -3 mol L -1 , 1 mL). Dilute to the mark with acetonitrile solution, shake well, transfer to a 1cm quartz cuvette for fluorescence spectrum and UV-visible absorption spectrum measurement. The excitation and emission wavelengths of the probe solution fluorescence spectrometry are 385 / 454nm.

[0099] The reagents used are analytical reagents, and the test water is double distilled water.

[0100] The model of the fluorescence spectrophotometer used is Cary Eclipse fluorescence spectrophotometer, manufactured by VARIAN Company of the United States. The ultraviolet-visible spectrophotometer model is UV-vis TU-1901, manufactured by Beijing General Instrument Co., Ltd.

[0101] In acetonitrile solution, the probe itself has weak fluorescence emission, the excitation wavelength is 385nm, the emission wavelength is 454nm, and the fluorescence emission is very weak ...

Embodiment 3

[0107] Add the probe's N,N-dimethylformamide stock solution (1.00×10 -4 mol L -1 , 1mL), cationic Zn 2+ (2.00×10 -3 mol L -1 , 1 mL). Dilute to the mark with N,N-dimethylformamide solution, shake well, transfer to a 1cm quartz cuvette for fluorescence spectrum and UV-visible absorption spectrum measurement. The excitation and emission wavelengths of the fluorescence spectrometers of the probes are 365 / 450 nm.

[0108] The reagents used are analytical reagents, and the test water is double distilled water.

[0109] The model of the fluorescence spectrophotometer used is Cary Eclipse fluorescence spectrophotometer, manufactured by VARIAN Company of the United States. The ultraviolet-visible spectrophotometer model is UV-vis TU-1901, manufactured by Beijing General Instrument Co., Ltd.

[0110]In N,N-dimethylformamide solution, the excitation wavelength is 365nm, and the emission wavelength is 450nm. The fluorescence emission of the probe itself is weak, and a very weak ...

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Abstract

The invention discloses a coumarin-thiacalix [4] arene fluorescent reagent as well as a preparation method and an application thereof, which belong to the chemical field of organic synthesis and analysis. The invention prepares an excellent coumarin-thiacalix [4] arene derivative which can be used for respectively detecting performances of fluorine ions and zinc ions. The preparation method of the coumarin-thiacalix [4] arene fluorescent reagent comprises the following steps of: respectively connecting two coumarin fluorescent groups at the lower 1,3-site of the calixarene and connecting two methoxyl ethyl at the 2,4-site through step by step reaction by using coumarin-thiacalix [4] arene and 7-hydroxycoumarin as starting materials to prepare the coumarin-thiacalix [4] arene fluorescent reagent. Under a special medium condition, the compound can be used as a dual-functional fluorescent or colorimetric reagent for detecting micro fluorine ions and zinc ions with high sensitivity and high selectivity by utilizing fluorescence spectrum and ultraviolet absorption spectrum.

Description

technical field [0001] The invention belongs to the field of organic synthesis and analytical chemistry, in particular to a coumarin-thiacalix[4]arene fluorescent reagent and its preparation method and application. Background technique [0002] Fluorescent probes are based on the organic combination of molecular recognition and fluorescence technology. Through the selective binding of receptors to specific objects, fluorescent signals are used to express molecular binding information, so as to realize in situ real-time detection at the molecular level. Analytical objects such as ions and molecules in many chemical related fields can be detected by fluorescent probes. For example, H + , Li + 、Na + 、K + , Ca 2+ , Hg 2+ , Zn 2+ , Pb 2+ 、A1 3+ and Cd 2+ , halide ion, citrate, carboxylate, phosphate, sugar, amino acid, O 2 , CO 2 and NO etc. Due to its high sensitivity and specificity, fluorescent probes have broad application prospects in analytical chemistry, bioch...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/14C09K11/06G01N21/64
Inventor 孙强曾晞牟兰赵远会
Owner GUIZHOU UNIV
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