Tetraphenyl ethylene Schiff base red-light zinc ion probe and preparation method and application

A tetraphenylethylene and Schiff base technology, applied in the field of analytical chemistry, can solve problems such as probe spectrum and instrument performance interference, and achieve the effects of strong resistance to other molecular interference, low synthesis cost, and reduced signal-to-noise ratio.

Inactive Publication Date: 2017-07-07
CHINA UNIV OF MINING & TECH
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Problems solved by technology

[0005] Most of the reported fluorescent probes for zinc ions are based on traditional fluorescent chromophores such as naphthalimide, coumarin, rhodamine, etc., and detect zinc ions through fluorescence quenching or single enhancement of fluorescence intensity, which is largely affected by Spectrum of the probe itself and instrument performance interference

Method used

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Embodiment

[0029] Synthesis of tetraphenylethylene Schiff base red light zinc ion probe compound HL proposed by the present invention

[0030] The synthetic route of compound HL is as follows:

[0031]

[0032] 1. Synthesis of Compound A:

[0033]

[0034] Diphenylmethane (12mmol, 2.02g) was dissolved in 50ml of tetrahydrofuran, at minus 20°C, under the protection of nitrogen, 2.5M n-butyllithium (10mmol, 4ml) was added dropwise, and 4-methoxybenzophenone (12mmol , 3.03g) was warmed up to room temperature, stirred for 3 hours, quenched with water, extracted with dichloromethane, the solvent was spun off, added toluene, p-toluenesulfonic acid (1.8mmol, 0.342g), refluxed for 6 hours, cooled to room temperature, 5% Wash twice with sodium bicarbonate, do with anhydrous magnesium sulfate, spin out the solvent to obtain a yellow crude product, and recrystallize to obtain compound A as a white solid product with a yield of 80%. 1 H NMR (400MHz, DMSO-d 6 )δ(TMS,ppm):7.19-7.06(m,9H),7.03...

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Abstract

The invention discloses a tetraphenyl ethylene Schiff base red-light zinc ion probe and a preparation method and application thereof. The synthesizing method of the compound is simple (short for HL), and a chemical structural formula thereof is shown in the following formula in the description. The probe can be used for detecting the zinc ion, the sensitivity is higher, and the detection line can reach 9*10<-8>. After proofing by eExperiments show that, the zinc ion fluorescent probe has the advantages that the zinc ion can be selectively detected; the fluorescent red movement occurs and is enhanced; the potential application value is realized in the field of labeling of zinc ion in the biological system.

Description

technical field [0001] The invention relates to a red light fluorescent probe for rapid detection of zinc ions, specifically a tetraphenylethylene Schiff base red light zinc ion probe and a preparation method thereof, which belong to the technical field of analytical chemistry. Background technique [0002] Zinc ions are the second most abundant transition metal in the human body and are widely distributed in the human body. For example, the adult body contains 2.3g of zinc in total, while the content of copper is only 250mg. What's more interesting is that a large amount of zinc ions exist in nerve tissue, for example, the concentration of zinc ions in brain tissue reaches 0.1-0.5mM. At present, the number of known enzymes containing zinc ions in their active centers exceeds 1,000, and zinc ions are present in all six types of enzymes, and zinc ions participate in all metabolic processes of cells. [0003] A large number of evidences in vivo and in vitro indicate that zin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/40C09K11/06G01N21/64
CPCC07D215/40C09K11/06C09K2211/1007C09K2211/1029G01N21/643
Inventor 倪中海聂景张丽芳赵云
Owner CHINA UNIV OF MINING & TECH
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