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Proportional sensing type zinc ion fluorescence probe and preparing method and application thereof

A technology of fluorescent probes and zinc ions, which is applied in the field of ion recognition, can solve problems such as non-specific recognition of zinc ions, and achieve the effect of simple and easy preparation method, high yield and good selectivity

Active Publication Date: 2019-05-21
SHANDONG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Chinese patent CN201711073438 discloses a class of o-phenanthroline derivatives, zinc ion fluorescent probes and their applications. A conjugated fluorophore is introduced into the parent ring of o-phenanthroline with a single bond, and the prepared ratio-sensitive fluorescent probe It also shows the shift of fluorescence emission wavelength for other metal ions except zinc ions, especially cadmium ions of the same main group, so it is not a probe for specific recognition of zinc ions

Method used

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  • Proportional sensing type zinc ion fluorescence probe and preparing method and application thereof
  • Proportional sensing type zinc ion fluorescence probe and preparing method and application thereof
  • Proportional sensing type zinc ion fluorescence probe and preparing method and application thereof

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Embodiment 1

[0037] A ratio-sensitive zinc ion fluorescent probe, the preparation method of which is:

[0038] (1)N 2 Under protection, 1mmol of tetrakis(triphenylphosphine)palladium, 10mmol of 3,5-dibromobenzaldehyde, 25mmol of pyridine-4-boronic acid, and 125mmol of potassium carbonate were dissolved in a mixed solvent of 50mL of toluene, 50mL of ethanol and 50mL of water, and heated to reflux After 36h, the reaction was left to cool, 160mL of dichloromethane was extracted, the solvent was evaporated under reduced pressure, and column chromatography was purified (dichloromethane and methanol were mixed at a volume ratio of 80:1) to obtain 3,5-bis(4-pyridine ) Benzaldehyde, the productive rate is 90%;

[0039] (2) Dissolve 10mmol 1,10-phenanthroline-5,6-dione, 10mmol 3,5-bis(4-pyridine)benzaldehyde, 15mmol p-methylaniline, and 50mmol ammonium acetate in 40mL acetic acid, and heat to reflux reaction. Add 30mL deionized water to filter, wash the precipitate with water, and purify by colu...

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Abstract

The invention belongs to the technical field of ion recognition and particularly relates to a proportional sensing type zinc ion fluorescence probe and a preparing method and application thereof. Thestructure of the probe is shown in the specification. The probe can quantitatively detect the zinc ion concentration and has good selectivity, high sensitivity and low zinc ion detection limit. The preparing method of the probe is also provided and includes adding 3,5-dibromobenzaldehyde, pyridine-4-boronic acid and potassium carbonate into a solvent mixture including toluene, ethanol and water, heating, refluxing and reacting the mixture to obtain 3,5-di(4-pyridinyl) benzaldehyde, with tetrakis(triphenylphosphine) palladium being adopted as a catalyst; then dissolving 1,10-phenanthroline-5,6-dione, the 3,5-di(4-pyridinyl) benzaldehyde, p-toluidine and ammonium acetate into acetic acid, and heating, refluxing and reacting the mixture to obtain 2-(3,5-di(4-pyridinyl)phenyl)-1-p-tolyl-1H-imidazo[4,5-f][1,10]phenanthroline. The synthetic process is simple and easy to achieve. Applications of the probe are also provided.

Description

technical field [0001] The invention belongs to the technical field of ion recognition, and in particular relates to a ratio-sensing zinc ion fluorescent probe and a preparation method and application thereof. Background technique [0002] Alzheimer's disease (AD) is a common chronic progressive neurodegenerative disease that mainly occurs in the elderly, and its typical pathological features include β-amyloid (Aβ) deposition to form senile plaques and neuronal Fibrillary tangles, cerebral amyloid angiopathy, and neuronal apoptosis. Due to the lack of effective treatment methods, AD has become the fourth fatal disease that endangers human health after heart disease, cancer and stroke in developed countries. In recent years, studies have found that metal ions, especially zinc ions (Zn 2+ ) plays a key role in the deposition of Aβ in the brain and participates in the pathogenesis of AD. Therefore, it is of great significance to detect the concentration of zinc ions. [0003...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14C09K11/06G01N21/64
Inventor 纪洪芳申亮徐昊秦洁王萌谢龙妍张宇龚畅达杜秀丽
Owner SHANDONG UNIV OF TECH
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