Ratio fluorescent fluorine ion probe, and preparation and applications thereof

A ratiometric fluorescence, fluoride ion technology, applied in the field of chemical/biosensors, can solve the problems of reducing detection sensitivity and signal-to-noise ratio, and achieve the effects of high selective detection, high sensitivity and improved accuracy

Active Publication Date: 2017-02-15
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 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 fluorescent signals. In practical applications, the detection of fluorescent signals is easily interfered by background fluorescence, which reduces the detection sensitivity and signal-to-noise ratio.

Method used

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  • Ratio fluorescent fluorine ion probe, and preparation and applications thereof
  • Ratio fluorescent fluorine ion probe, and preparation and applications thereof
  • Ratio fluorescent fluorine ion probe, and preparation and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Probe Ir1, namely Ligand is The preparation and application test of the probe material:

[0047] The preparation method of probe Ir1 is shown in the following equation and steps:

[0048]

[0049] (1) Preparation of Compound 3: Add 2,7-dibromo-fluorene (10.0g, 60.2mmol), finely powdered potassium hydroxide (1.69g, 30.1mmol) and 1-octanol (40g , 0.31mol), stirred and heated to 190°C for 19h. The reaction mixture was cooled to room temperature, and excess 1-octanol was distilled off under reduced pressure. The crude product was passed through a dry silica gel column with n-hexane as eluent to obtain 2,7-dibromo-9-octyl-fluorene (86%). 1 H NMR (400MHz, CDCl 3 ): δ=7.62(d, J=1.7Hz, 2H), 7.56(d, J=8.1Hz, 2H), 7.49(dd, J=1.7Hz and 8.1Hz, 2H), 3.95(t, J=5.8 Hz, 1H), 1.90-2.04(m, 2H, CH 2 ), 1.06-1.35 (m, 12H, 6×CH 2 ), 0.87(t, J=6.7Hz, 3H, CH 3 ); 13 C NMR (100MHz CDCl 3 ,): δ = 149.2, 139.0, 130.1, 127.6, 121.1, 121.0, 47.4, 32.6, 31.7, 29.7, 29.2, ...

Embodiment 2

[0066] Embodiment 2: probe Ir2, promptly when Ligand is The preparation and application test of the probe material:

[0067] The preparation method of probe Ir2 is shown in following equation and steps:

[0068] (1) Preparation of Compound 3: Add 2,7-dibromo-fluorene (10.0g, 60.2mmol), finely powdered potassium hydroxide (1.69g, 30.1mmol) and 1-octanol (40g , 0.31mol), stirred and heated to 150-220 ° C overnight. The reaction mixture was cooled to room temperature, and excess 1-octanol was distilled off under reduced pressure. The crude product was passed through a dry silica gel column with n-hexane as eluent to obtain 2,7-dibromo-9-octyl-fluorene (86%).

[0069] (2) Preparation of Compound 4: Add potassium hydroxide 51mmol and 2-pyridylbenzimidazole 10.2mmol in the reaction flask, and add 1-butyl-3-methylimidazolium hexafluorophosphate (ionic liquid) 20ml . After the mixture was pre-stirred for 5 min, 8 ml of 1,6-dibromohexane was added, and the reaction was stirre...

Embodiment 3

[0086] Embodiment 3: probe Ir2, promptly when Ligand is The preparation and application test of the probe material:

[0087] The preparation method of probe Ir3 is shown in following equation and steps:

[0088] The preparation process of compounds 3, 4 and 5 was consistent with that in Example 2.

[0089]

[0090] The preparation of compound 6c: Weigh compound 5 (0.71g, 1mmol), phenylboronic acid (0.28g, 2.3mmol) and tetrakis (triphenylphosphine) palladium (0.05g, 0.04mmol) join in two-necked flask, and to The reaction device is protected from light, and then vacuum-filled with nitrogen-vacuumized on the double-row tube, and the cycle is three times, and finally the reaction system is protected with nitrogen. 2M aqueous sodium carbonate solution (2.5 mL), toluene (5.0 mL) and ethanol (2.5 mL) were deoxygenated by bubbling nitrogen gas respectively, and injected into the reaction system with a syringe. Raise the temperature to 30-110°C. Then, the reaction system was ...

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Abstract

The invention relates to a ratio fluorescent fluorine ion probe, and a preparation method and applications thereof in the fluorine ion detection, cell marking, and imaging fields. The probe is mainly composed of two parts. One part is a fluorescence energy donor. The other part is an ionic iridium complex containing an isobutyl diphenyl siloxy group and is taken as an energy acceptor. Two parts are connected through a covalent bond. In the ligand, after the silicon-oxygen bond reacts with a fluorine ion, the silicon-oxygen bond is broken, the excited state and photophysical property of the iridium complex are changed, thus the efficiency of energy transfer between the energy donor and the energy acceptor is influenced, and the ratio fluorescent detection of fluorine ions is realized. The complex can also be applied to biological ratio imaging. The provided compound can be used as a fluorine ion phosphorescence sensor to detect the fluorine ions in water high sensitively and high selectively. The ratio detection and colorimetric detection can be realized, the interference of fluorescence in the background is eliminated, and the detection accuracy is improved. The n represents an integer from 1 to 10.

Description

technical field [0001] The invention belongs to the technical field of chemical / biological sensors, and in particular relates to a ratio fluorescent fluoride 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, fluo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06G01N21/64
CPCC07F15/004C09K11/06C09K2211/185G01N21/643G01N21/6486
Inventor 赵强杨继光许文娟黄维刘淑娟秦妍妍
Owner NANJING UNIV OF POSTS & TELECOMM
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