Fluorescent probe, preparation method thereof and application in the detection of iron ions

A fluorescent probe and fluorescence quenching technology, applied in the field of fluorescence sensing, can solve the problems of interference and detection limit, and achieve the effects of high yield, simple operation and high purity

Active Publication Date: 2019-08-23
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

reported for Fe 3+ The detected fluorescent small molecule materials mainly include rhodamine molecules, tetraphenylethylene molecules, quinoline molecules and BODIPY molecules, etc. However, these fluorescent small molecule materials cannot exclude other metal ions such as Zn during the detection of iron ions. 2+ interference defects, and the Fe 3+ higher detection limit

Method used

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  • Fluorescent probe, preparation method thereof and application in the detection of iron ions
  • Fluorescent probe, preparation method thereof and application in the detection of iron ions
  • Fluorescent probe, preparation method thereof and application in the detection of iron ions

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preparation example Construction

[0054] The present invention also provides a method for preparing the fluorescent probe described in the above technical solution, comprising the following steps:

[0055] In a protective atmosphere, a halogenated aromatic hydrocarbon, an organoboron compound, a solvent, a basic reagent and a catalyst are mixed for a Suzkki-Miyaura reaction to obtain a fluorescent probe; the halogenated aromatic hydrocarbon includes 3,4-(bromophenyl) -5-phenyl-4H-1,2,4-triazole, 3,5-(bromophenyl)-4-phenyl-4H-1,2,4-triazole, 3,4,5 -Triphenyl-4H-1,2,4-triazole, 4-biphenyl-3,5-diphenyl-4H-1,2,4-triazole, 4-triphenylamino-3 , 5-diphenyl-4H-1,2,4-triazole or 4-benzocarbazolyl-35-4H-1,2,4-triazole; the organoboron compound includes 2-(4 ,4',5,5'-Tetramethyl-1,3,2-dioxaboron)-9,9'-di(N-carbazole-hexyl)fluorene, 1-(4,4',5 ,5'-tetramethyl-1,3,2-dioxaborin)-benzene or 1-(4,4',5,5'-tetramethyl-1,3,2-dioxaborin) - Biphenyl.

[0056] In the present invention, unless otherwise specified, all raw materia...

Embodiment 1

[0074] TAZ-1 (0.4g, 0.88mmol, see the specific structure in the subsequent preparation route), 2-(4,4',5,5'-tetramethyl-1,3,2-dioxaboron)-9 , 9'-dihexylfluorene (2.085g, 2.64mmol), toluene (20mL), ethanol (7mL) and potassium carbonate aqueous solution (15mL, 2mol / L) were placed in a 100mL round bottom flask; under the protection of argon, Freeze with liquid nitrogen for 8 minutes and then vacuumize for 8 minutes, then add the catalyst Pd (PPh 3 ) 4 (61.0mg, 0.053mmol), re-seal the device; sequentially freeze in liquid nitrogen for 8min and vacuumize for 8min, repeat the freezing-vacuumizing operation 3 times in total, and react at 85°C for 48h; after cooling to room temperature, in the resulting reaction solution Add deionized water, use dichloromethane to extract, the obtained organic phase is concentrated and then purified by column chromatography, wherein the eluent is dichloromethane:petroleum ether=1:1 (v / v), to obtain a compound with the formula NC-TAZ Fluorescent prob...

Embodiment 2

[0077] TAZ-2 (0.4g, 0.88mmol, see the following preparation route for specific structure), 2-(4,4′,5,5′-tetramethyl-1,3,2-dioxaboron)-9 , 9'-dihexylfluorene (2.085g, 2.64mmol), toluene (20mL), ethanol (7mL) and anhydrous potassium carbonate aqueous solution (15mL, 2mol / L) were placed in a 100mL round bottom flask; , freeze with liquid nitrogen for 8 minutes and then vacuumize for 8 minutes, then add the catalyst Pd (PPh 3 ) 4(61.0mg, 0.053mmol), re-seal the device; sequentially freeze in liquid nitrogen for 8min and then vacuumize for 8min, repeat the operation 3 times, and react at 85°C for 48h; after cooling to room temperature, add deionized water to the resulting reaction solution , extracted with dichloromethane, concentrated the obtained organic phase and purified by column chromatography, wherein the eluent is dichloromethane:petroleum ether=1:1 (v / v), to obtain the compound having the structure shown in formula CC-TAZ Fluorescent probe (abbreviated as CC-TAZ; white p...

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Abstract

The invention provides a fluorescent probe, a preparation method thereof and an application in the detection of iron ions, belonging to the technical field of fluorescent sensing. In the fluorescent probe provided by the invention, a rigid main chain M provides an active site for the complexation of iron ions, the periphery of the main chain is connected with R1 group, the solubility of the fluorescent probe is improved, the fluorescent probe is easily dissolved in a solvent to form a homogeneous solution, and the detection of iron ions is realized; moreover, the conjugation degree of the fluorescent probe can be further improved by the presence of R3 and R2 groups, and the fluorescence efficiency of the fluorescent probe can be further improved. The fluorescent probe provided by the invention has a good linear relationship in the range of 1-10Mum when detecting iron ions, the fluorescence quenching rate of the fluorescent probe for iron ion solution is as high as 84%, and the detection limit is as low as 33nM, which indicates that the fluorescent probe provided by the invention has high sensitivity, good selectivity and low detection limit for iron ions.

Description

technical field [0001] The invention relates to the technical field of fluorescent sensing, in particular to a fluorescent probe, a preparation method thereof and an application in iron ion detection. Background technique [0002] Iron is an indispensable trace element in the human body and an important component of hemoglobin, which is responsible for the transport of oxygen in living organisms. In addition, iron is involved in the composition of various immune systems and enzymes in the human body. The lack of iron in the body will cause iron deficiency anemia, insufficient cell supply, fatigue and burnout, and at the same time lead to a decline in human immunity. Iron deficiency in childhood will affect children's psychological activities and intellectual development, and the process is irreversible. Excess iron in the human body will lead to iron overload in the liver, causing diseases such as liver fibrosis and hepatoma, and even lead to an imbalance in the body's oxi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C09K11/06G01N21/64
CPCC07D403/14C09K11/06C09K2211/1059G01N21/6428G01N2021/6432
Inventor 张明冯宇婷
Owner JILIN UNIV
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