Fluorescent probe reagent for concurrent selection and determination of multiple metal ions, and preparation and appliance

A metal ion and multi-metal technology, applied in the field of probe reagents for simultaneous selection and determination of multi-metal ions, can solve problems such as unreported

Inactive Publication Date: 2016-04-13
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the existing reports of tripod fluorescent probes, most of them focus on the detection of Fe 3+ 、Cu 2+ , Zn 2+ 、Al 3+ 、Cr 3+ The recognition and detection of single ions, such as the recognition of citrate and Cu at the same time have also been reported 2+ and other single probes, and a single probe can realize the separate detection of multiple ions at the same time, which has not been reported so far

Method used

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  • Fluorescent probe reagent for concurrent selection and determination of multiple metal ions, and preparation and appliance
  • Fluorescent probe reagent for concurrent selection and determination of multiple metal ions, and preparation and appliance
  • Fluorescent probe reagent for concurrent selection and determination of multiple metal ions, and preparation and appliance

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Embodiment one: the synthesis of intermediate:

[0095] In a 250ml three-neck flask, add rhodamine B (1.64g, 3.42mM) and 60mL of ethanol. in N 2 Under protection, the temperature was raised to 78°C, and tris(2-aminoethyl)amine (4.0 g, 27.36 mM) was gradually added dropwise at a rate of 1 drop per second, and refluxed for 36 h until the solution became colorless. The solvent ethanol was evaporated, 60 mL of water was added, and extracted three times with dichloromethane (60 mL×3), and the organic phases were combined. Dry with anhydrous magnesium sulfate, filter, and evaporate the solvent to obtain a red oily liquid, which is purified by column chromatography, and the eluent is: chloroform / methanol / triethylamine (v / v / v=9 / 1 / 1), to obtain 1.52g colorless oily liquid intermediate, yield 77.6%.

Embodiment 2

[0096] Embodiment two: the synthesis of product:

[0097] In a 250ml three-neck flask, add the intermediate (1.10g, 1.92mM), 2-hydroxy-1-naphthaldehyde (660mg, 3.84mM), dissolve in 100mL of methanol, and heat up to 40°C. in N 2 Reflux overnight under protection, evaporate the solvent, and purify by silica gel column chromatography under reduced pressure. The collection rate of the eluent is 25-30ml per minute. The eluent is chloroform, and 1.5g of yellow solid is obtained, with a yield of 85.2%. 1 HNMR (500MHz, CD 3 OD)δ:14.214(s,2H,OH),8.611(s,2H,CH=N),7.924(d,J=4.5Hz,1H,Ar-H),7.774(d,J=8.5Hz,2H ,Ar-H),7.546(d,J=9.5Hz,2H,Ar-H),7.507(d,J=8.0Hz,2H,Ar-H),7.475(t,J=4.5Hz,2H,Ar -H),7.330(t,J=7.5Hz,2H,Ar-H),7.157(t,J=7.5Hz,2H,Ar-H),7.116(t,J=4.5Hz,1H,Ar-H ),6.790(d,J=9.5Hz,2H,Ar-H),6.435(d,J=8.5Hz,2H,Ar-H),6.392(d,J=2.5Hz,2H,Ar-H), 6.265(d,J=9.0Hz,2H,Ar-H),3.448(s,4H,CH 2 CH 2 N=C),3.285-3.244(m,10H,NCH 2 CH 3 ,CH 2 CH 2 N-CO), 3.726(t, J=6.0Hz, 4H, CH 2 CH 2N=C),2.496...

Embodiment 3

[0099] The preparation method of various reagents in the analytical method of the present invention is:

[0100] (1) Preparation method of the probe solution: weigh 88mg of the probe (molecular formula: C 56 h 58 N 6 o 4

[0101] Molecular weight: 879.10), 1,4-dioxane was dissolved and prepared into 100mL of a solution with a concentration of 1mM.

[0102] (2) Cu 2+ Stock solution preparation method: weigh 0.1853g of copper perchlorate, dissolve in water, and prepare 50mL of a solution with a concentration of 10mM.

[0103] (3) Co. 2+ Stock solution preparation method: weigh 0.1830 g of cobalt perchlorate, dissolve it in water, and prepare 50 mL of a solution with a concentration of 10 mM.

[0104] (4) Fe 3+ Stock solution preparation method: Weigh 0.1171g of ferric perchlorate, dissolve it in water, and prepare 50mL of a solution with a concentration of 10mM.

[0105] (5) Zn 2+ Stock solution preparation method: Weigh 0.1321g of zinc perchlorate, dissolve it in wate...

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Abstract

The invention discloses a probe reagent for concurrent selection and determination of multiple metal ions, and preparation and appliance, and belongs to the field of organic synthesis and analytical chemistry. Tri (2-aminoethyl) amine serves as a parent, wherein rhodamine B is connected to an amino chain, 2-hydroxy-1-naphthaldehyde groups are connected to other two amino chains respectively, and thus a tripod structured rhodamine-hydroxyl naphthalene derivative probe is prepared. In 1,4-dioxane/water (19/1, v/v, pH=7) solution, the probe respectively detects Cu2+, Co2+ and Fe3+ by utilizing rate absorption of different wavelengths, and the detection does not interfere with each other; in acetonitrile/water (19/1, v/v) solution, fluorescence emission of different wavelengths under different pHs is utilized, the probe respectively detects Zn2+, Al3+, Hg2+ and Cu2+, and the detection does not interfere with each other; under an ultraviolet lamp of 365 nm, Zn2+, Al3+ and Hg2+ are detected to show blue, pink and orange red fluorescence respectively, and through -Zn2+ mixture detection by the probe, Cu2+ shows blue fluorescence vanishing. The probe structure is as follows.

Description

technical field [0001] The invention belongs to the field of organic synthesis and analytical chemistry, in particular to a probe reagent for simultaneous selective determination of multiple metal ions, and its preparation and application. Background technique [0002] The detection of fluorescent probes to targets is expressed as spectral changes through recognition, and the recognition performance depends on the binding site and luminescent properties of the probe molecule. Simultaneously realizing the separate detection of multiple metal ions is the goal pursued by the design of probe molecules. Single-probe multi-target analysis enables fast, efficient and economical testing in a short period of time. The main method of fluorescent probe application is to realize the detection of specific target molecules and ions by using absorption and fluorescence enhancement or quenching and spectral changes. Compared with single wavelength assay methods, ratiometric absorbance det...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/107G01N21/31G01N21/64
CPCC07D491/107C09K11/06C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088G01N21/314G01N21/643G01N2021/6432
Inventor 曾晞冉茂乾袁剑英牟兰吴玉田曾莉
Owner GUIZHOU UNIV
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