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Fluorescent probe for simultaneously detecting aluminum ions and zinc ions and preparation and application of fluorescent probe

A technology of fluorescent probes and zinc ions, which is applied in the field of fluorescent probes for metal ion detection, can solve the problems of rare bifunctional probes, achieve good selectivity, anti-interference ability, and easy purification

Active Publication Date: 2021-02-23
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, many probes for the detection of aluminum ions or zinc ions alone have been reported, and there are also a few reports for the detection of aluminum ions and zinc ions at the same time. Probes are extremely rare

Method used

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  • Fluorescent probe for simultaneously detecting aluminum ions and zinc ions and preparation and application of fluorescent probe
  • Fluorescent probe for simultaneously detecting aluminum ions and zinc ions and preparation and application of fluorescent probe
  • Fluorescent probe for simultaneously detecting aluminum ions and zinc ions and preparation and application of fluorescent probe

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preparation example Construction

[0032]A method for preparing a fluorescent probe for simultaneously detecting aluminum ions and zinc ions, including the following steps:

[0033](1) Add 1-(4-bromophenyl)-1,2,2-tristyrene, p-formylphenylboronic acid, tetrakis(triphenylphosphine)palladium, and anhydrous potassium carbonate to the round bottom reaction flask , Wherein the molar ratio of 1-(4-bromophenyl)-1,2,2-tristyrene, p-formylbenzeneboronic acid, tetrakis(triphenylphosphine)palladium and anhydrous potassium carbonate is 1:1.2:0.05 :5, use ethylene glycol dimethyl ether and deionized water as solvents, where the volume ratio of ethylene glycol dimethyl ether and water is 1:5, under nitrogen atmosphere, reflux and stir for 12 hours, and purified to obtain (II) Compound:

[0034]

[0035](2) Dissolve compound (II) in absolute ethanol, add o-aminophenol, the molar ratio of compound (II) to o-aminophenol is 1:2, under nitrogen atmosphere, reflux and stir for 6h to obtain (I) The compound shown.

[0036]A method for preparing the ...

Embodiment 1

[0042]Example 1: Synthesis of probe

[0043](1) First, compound (II) is synthesized by Suzuki reaction.

[0044]The specific steps are as follows: Combine 1-(4-bromophenyl)-1,2,2-tristyrene (1mmol; 411mg), p-formylphenylboronic acid (1.2mmol; 180mg), tetrakis(triphenylphosphine) palladium (0.05mmol; 58mg), anhydrous potassium carbonate (5mmol; 691mg) were added to a 100mL two-necked reaction flask, with ethylene glycol dimethyl ether (15mL) and deionized water (3mL) as solvents, under nitrogen atmosphere, reflux Stir for 12h. After the reaction, it was cooled to room temperature, the reaction solution was extracted with dichloromethane, and dried with anhydrous magnesium sulfate, the solvent was removed by a rotary evaporator under reduced pressure, and finally petroleum ether: dichloromethane (15:1, v:v) was used as The eluent was separated by silica gel column chromatography to obtain a light green product with a yield of 58%.

[0045]1H NMR (600MHz, Chloroform-d) δ 10.03 (s, 1H), 7.91 (d,...

Embodiment 2

[0049]Example 2: Fluorescence detection of aluminum ion and zinc ion by probe in aqueous solution

[0050]Prepare Al with a concentration of 10-2M separately3+,Fe3+,Co2+,Mg2+,Ni2+,Ag+,Cu2+,Pb2+,Mn2+,Zn2+,K+,Cd2+,Hg2+,Cr3+,Ca2+,Na+Aqueous solution.

[0051]The acetone solution of the probe prepared in Example 1 was prepared with a concentration of 2.5 mM. The prepared various metal ion solutions (10-2M, 10μL) was added to the probe (2.5mM, 100μL) and diluted with deionized water to a total volume of 10ml. A steady-state fluorescence spectrophotometer was used to measure the influence of the addition of different ions on the fluorescence intensity. Such asfigure 1 with2As shown, only the addition of aluminum ions and zinc ions can cause the fluorescence intensity to change: adding aluminum ions, the fluorescence intensity at 492nm is significantly increased, showing cyan fluorescence; adding zinc ions, the fluorescence intensity at 592nm is significantly increased, showing orange fluorescen...

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Abstract

The invention belongs to the field of fluorescent probes for metal ion detection, and particularly relates to a fluorescent probe for simultaneously detecting aluminum ions and zinc ions and a preparation and application of the fluorescent probe. The preparation method comprises the following steps: carrying out Suzuki reaction on 1-(4-bromophenyl)-1, 2, 2-triphenylethylene and p-formylphenylboronic acid according to a certain ratio under certain conditions to obtain an intermediate [1-(4-formaldehyde biphenyl)-1, 2, 2-triphenyl] ethylene, and carrying out aldehyde amine condensation reactionon the intermediate and o-aminophenol in absolute ethyl alcohol to obtain the target product. The probe is simple in synthesis method and mild in reaction condition.In an approximate aqueous solutionsystem, the probe shows cyan blue fluorescence turn-on for aluminum ions and shows orange red fluorescence turn-on for zinc ions. The probe has good selectivity and high sensitivity on aluminum ions and zinc ions, and has certain application potential in the aspect of environmental metal ion detection.

Description

Technical field[0001]The invention belongs to the field of fluorescent probes for detecting metal ions, and specifically relates to a preparation method and application of a fluorescent probe capable of simultaneously detecting aluminum ions and zinc ions.Background technique[0002]Aluminum is the third most abundant substance on earth. As a non-essential element for the human body, the widespread use of aluminum causes the human body to consume too much aluminum. Excessive aluminum can cause damage to the human central nervous system and immune system, and lead to a variety of brain diseases, such as Parkinson’s disease. Alzheimer's disease, etc. Zinc is the second most abundant transition metal element in the human body. Zinc ions participate in many physiological activities in the human body, such as brain function, gene transfection, immune function, and central nervous signal transmission. It is precisely because of the importance of aluminum ion and zinc ion to life that it is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C251/24C07C249/02G01N21/64
CPCC09K11/06C07C249/02C07C251/24C07C45/68G01N21/643C09K2211/1007C09K2211/1014C07C47/548
Inventor 郭鹍鹏李达张芳梁效中李洁李斌徐洪张征王思静
Owner TAIYUAN UNIV OF TECH
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