Coumarin-oxacalix[3]arene fluorescent reagents as well as preparation method and application thereof

A kind of aromatic hydrocarbon fluorescence, coumarin technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of rare fluorescent probes and limited research on fluorescent probes

Inactive Publication Date: 2013-12-11
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Currently, detection of Fe 3+ The coumarin-oxacalix[3] fluorescent probes are rare, and the research on fluorescent probes that can only detect ferric ions without interference from copper ions and cobalt ions is extremely limited

Method used

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  • Coumarin-oxacalix[3]arene fluorescent reagents as well as preparation method and application thereof
  • Coumarin-oxacalix[3]arene fluorescent reagents as well as preparation method and application thereof
  • Coumarin-oxacalix[3]arene fluorescent reagents as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] (1) Intermediates 1a (7,15,23-tri-tert-butyl-25,26,27-tripropyne-3,11,19-trioxacalix[3]arene) and 1b Synthesis of (7,15,23-triethoxycarbonyl-25,26,27-tripropyne-3,11,19-trioxacalix[3]arene)

[0092] Under nitrogen protection, 0.3g (0.52 mmol) p-tert-butyloxacix[3]arene and 1.69g (5.2 mmol) cesium carbonate were dissolved in 15mL dry acetone, stirred and heated to reflux for 1h, then added 3-bromopropyne ( 0.62g, 5.2 mmol) and dry acetone (10mL), continue to reflux for 18h. Cool to room temperature at the end of the reaction, evaporate acetone under reduced pressure, extract with 10% hydrochloric acid and dichloromethane, dry over anhydrous magnesium sulfate, filter, evaporate the solvent, column chromatography (chloroform:petroleum ether) V : V =2:1) ​​eluted to give 0.16g colorless solid 1a , yield 44.6%. m.p.105.8-108.2°C; 1 H-NMR (400MHz, CDCl3 ), δ(ppm): 1.30 (s, 18H, tBu), 1.36 (s, 9H, tBu), 1.99 (t, 1H, J=2.4Hz, -CC-H), 2.42 (t, 2H, J= 2.4 Hz, -CC-H), 2.85 ...

Embodiment 2

[0103] Add compound to 10.0 mL volumetric flask a Dimethyl sulfoxide stock solution (1.00×10 -4 mol L -1 , 1.0mL), metal ion Fe 3+ (2.00×10 -3 mol L -1 , 1.0mL), tris-hydrochloric acid (Tris-HCl) buffer solution (1.00×10 -3 mol×L -1 , 1.0 mL), secondary water (3 mL), dilute to the mark with dimethyl sulfoxide solution, shake well, stand at room temperature for 10 min, transfer to a 1 cm quartz cuvette for fluorescence spectrum and UV-visible absorption spectrum measurement. The excitation and emission wavelengths for fluorescence spectrometry are 321 / 403 nm.

[0104] The reagents used are analytical reagents, and the test water is double distilled water.

[0105] 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 Puyi General Instrument Company.

[0106] Compound a It has ...

Embodiment 3

[0111] Add compound to 10.0 mL volumetric flask b Dimethyl sulfoxide stock solution (1.00 × 10 -4 mol L -1 , 1.0mL), metal ion Fe 3+ (2.00×10 -3 mol L -1 , 1.0mL), Tris-HCl buffer solution (1.00×10 -3 mol×L -1 , 1.0 mL), secondary water (6.0 mL). Dilute to the mark with dimethyl sulfoxide solution, shake well, stand at room temperature for 15 minutes, transfer to a 1cm quartz cuvette for fluorescence spectrum and ultraviolet-visible absorption spectrum measurement. The excitation and emission wavelengths of fluorescence spectrometry are 324 / 406nm.

[0112] Compound b It has strong fluorescence emission, the excitation wavelength is 324nm, and the emission wavelength is 406nm. It is observed to emit strong blue fluorescence under a 365nm ultraviolet lamp. After adding ferric ions, it was observed that the fluorescence emission intensity decreased significantly (quenching rate 73.52%), and other metal ions Al 3+ , Cr 3+ , Hg 2+ ,Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ ...

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Abstract

The invention discloses coumarin-oxacalix[3]arene fluorescent reagents as well as a preparation method and application thereof, and belongs to the fields of organic synthesis and analytical chemistry. The invention respectively synthesizes two coumarin-oxacalix[3]arene fluorescent reagents: chemical name a: 7,15,23-tertiary butyl-25,26,27-tri{1-[N-(7-coumarin oxyethyl)-1,2,3-triazole]-4-methoxy}-3,11,19-trioxacalix[3]arene; b: 7,15,23-triethoxycarbonyl -25,26,27-tri{1-[N-(7-coumarin oxyethyl)-1,2,3-triazole]-4-methoxy}-3,11,19-trioxacalix[3]arene. Meanwhile, the invention discloses a synthesis method and process conditions. According to the invention, the two coumarin-oxacalix[3]arene fluorescent reagents, in detecting ferric ions, have characteristics of high selectivity and high sensitivity; the fluorescent reagents are applicable to qualitative and quantitative analysis.

Description

technical field [0001] The invention belongs to the field of organic synthesis and analytical chemistry, in particular to a class of coumarin-oxaccalix[3]arene fluorescent reagent and its preparation and application. Background technique [0002] Molecular recognition and microscopic detection and research at the molecular level have important scientific significance and application value. Fluorescent probes are a class of molecules that can effectively express the molecular recognition process through fluorescent signals. They are widely used in the fluorescence recognition and detection of target substances such as cations, anions, and neutral molecules. Among many analytical methods, fluorescent probe technology has the advantages of high sensitivity, good selectivity, short response time, and direct observation, so it has attracted extensive attention in many fields such as chemistry, biology, and medicine in recent years. [0003] Fluorescent probes are based on the or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C09K11/06G01N21/64
Inventor 李燕琴曾晞牟兰陈义李俊
Owner GUIZHOU UNIV
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