Phosphorescent fluorinion probe, preparation and applications thereof

A fluoride ion and probe technology, applied in the field of chemical/biosensors, can solve the problems of reducing detection sensitivity and signal-to-noise ratio, and achieve the effect of good selectivity

Inactive Publication Date: 2014-07-23
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current fluorescent probes based on the interaction between silicon and fluorine to realize the detection of fluorine ions are all based on the detection of fluorescence signals. In practical applications, the detection of fluorescence signals is easily interfered by background fluorescence, which reduces the detection sensitivity and signal-to-noise ratio.

Method used

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  • Phosphorescent fluorinion probe, preparation and applications thereof
  • Phosphorescent fluorinion probe, preparation and applications thereof
  • Phosphorescent fluorinion probe, preparation and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation of embodiment 1, iridium complex, when Ligand is Time:

[0033] Compound 1: Preparation of 4-(Benzothiazol-2-yl)phenol

[0034]

[0035] Preparation of 4-(benzothiazol-2-yl)phenol: Weigh 2-aminobenzenethiol (4g) and p-hydroxybenzaldehyde (4.12ml), add them to a two-necked bottle, and vacuumize on the double-row tube- Nitrogen filling-vacuumizing, cycle three times, and finally protect the reaction system with nitrogen. Add pure N,N dimethylformamide (5ml) into the reaction flask, stir, and raise the temperature of the reaction system to 110°C, and the reaction time is about 72 hours. Treatment: Extract with water and ethyl acetate, spin dry in vacuo, and recrystallize from ethanol. Yield: 90%. 1 H NMR (400MHz,DMSO)δ10.21(s,1H),8.07(d,J=7.9Hz,1H),8.00–7.87(m,3H),7.53–7.45(m,1H),7.43–7.33( m,1H),6.97–6.88(m,2H).

[0036] Compound 2: Preparation of C^N Ligand

[0037]

[0038] Preparation of C^N ligand: Weigh 4-(benzothiazol-2-yl)phenol (1g)...

Embodiment 2

[0048] Embodiment 2, the preparation of iridium complex, when Ligand is Time:

[0049] Compound 1: Preparation of 4-(Benzothiazol-2-yl)phenol

[0050]

[0051] Preparation of 4-(benzothiazol-2-yl)phenol: Weigh 2-aminobenzenethiol (4g) and p-hydroxybenzaldehyde (4.12ml), add them to a two-necked bottle, and vacuumize on the double-row tube- Nitrogen filling-vacuumizing, cycle three times, and finally protect the reaction system with nitrogen. Add pure N,N dimethylformamide (5ml) into the reaction flask, stir, and raise the temperature of the reaction system to 110°C, and the reaction time is about 72 hours. Treatment: Extract with water and ethyl acetate, spin dry in vacuo, and recrystallize from ethanol. Yield: 90%. 1 H NMR (400MHz,DMSO)δ10.21(s,1H),8.07(d,J=7.9Hz,1H),8.00–7.87(m,3H),7.53–7.45(m,1H),7.43–7.33( m,1H),6.97–6.88(m,2H).

[0052] Compound 2: Preparation of C^N Ligand

[0053]

[0054] Preparation of C^N ligand: Weigh 4-(benzothiazol-2-yl)phenol (1g)...

Embodiment 3

[0063] Example 3: UV-visible spectrum test of the complex’s response to fluoride ions: Prepare a 40 μM complex solution (tetrahydrofuran solvent), pipette 2 mL of the complex solution into a fluorescence cuvette, and gradually add 0-5 eq of pure water dropwise for The fluoride ion solution of the solvent until it reaches equilibrium (that is, the spectrum no longer changes significantly), and the UV-visible emission spectra of no addition and dropwise addition of different contents of semi-fluoride ions are measured, as shown in figure 1 . The test data show that: with the addition of fluoride ions, the absorption peak around 400nm increases.

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Abstract

The invention relates to a phosphorescent fluorinion probe based on an iridium complex, a preparation method thereof, and applications of the probe in the fields of fluorinion detection, and cell marking and imaging. The C^N ligand of the ionic type iridium complex comprises an isobutyl biphenyl Si-O group whose structural formula is shown in the description. When the ligand carries out reactions with fluorine ions, the Si-O bond will be broken, thus the excitation state and photo-physical property of the iridium complex are changed, so the fluorinion detection is achieved. The iridium complex can also be applied to the field of cell marking and imaging.

Description

technical field [0001] The invention belongs to the technical field of chemical / biological sensors, and in particular relates to a phosphorescent fluorine ion probe and its preparation and application in the fields of aqueous phase fluorine ion detection and cell imaging. Background technique [0002] Biorecognition and biosensing have become an important research field, especially the detection of anions has become particularly important. Fluorine exists widely in nature, and fluoride is one of the essential trace elements for the human body. But at the same time, fluorine-containing compounds are toxic, and the toxicity of fluoride to the human body depends on the concentration and intake of fluoride ions. The appropriate concentration of fluoride in drinking water is 0.5-1.0mg / L. Long-term drinking of high-fluoride water will bring adverse effects to the human body, and serious cases will cause dental fluorosis and bone disease. As important chemical substances, fluorin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F15/00G01N21/31G01N21/33G01N21/64C12Q1/02
Inventor 赵强黄维赵新许文娟刘淑娟
Owner NANJING UNIV OF POSTS & TELECOMM
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