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Novel coumarin conjugated heterocyclic fluorescent probe for detecting Fe (III)

A coumarin-based, fluorescent probe technology, used in fluorescence/phosphorescence, luminescent materials, measuring devices, etc., can solve the problems of small Stokes shift, high detection limit, low college specificity, etc., and it is easy to achieve reaction conditions. Controlled, high yield, and stable fluorescence properties

Active Publication Date: 2020-07-17
NANCHANG HANGKONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The present invention is aimed at existing and is used for detecting Fe 3+ The fluorescent probe has the problems of low specificity, small Stokes shift and high detection limit due to the influence of other paramagnetic cations. It provides a new detection method for Fe 3+ Fluorescent probe and preparation method thereof

Method used

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  • Novel coumarin conjugated heterocyclic fluorescent probe for detecting Fe (III)
  • Novel coumarin conjugated heterocyclic fluorescent probe for detecting Fe (III)
  • Novel coumarin conjugated heterocyclic fluorescent probe for detecting Fe (III)

Examples

Experimental program
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Effect test

Embodiment 1

[0037] (1) Synthesis of 3-bromo-7-diethylaminocoumarin

[0038] Dissolve 2g of 7-diethylaminocoumarin (9.2mmol) in 20mL of glacial acetic acid, stir the solution at room temperature to turn reddish brown, then add 500μL (9.7mmol) of liquid bromine, and react at room temperature for 6h. The reaction was monitored by TLC. After the reaction was complete, part of the solvent was removed under reduced pressure, and then an appropriate amount of acetonitrile was added to the solution to precipitate a white solid, which was suction filtered, washed, and dried. The crude product was purified by column chromatography (dichloromethane / petroleum ether 1:20) to obtain 2.4 g of the product 7-diethylaminocoumarin (yield 88.6%).

[0039] (2) Synthesis of 3-(2-(trimethylsilyl)ethynyl)-1,10-phenanthroline

[0040] Take 2.6g 3-bromo-1,10-phenanthroline (0.01mol), 23.6mg palladium chloride (0.13mmol), 25mg cuprous iodide (0.13mmol), 68.7mg triphenylphosphine (0.26mmol) Dissolve in appropriate...

Embodiment 2

[0048] (1) Probe M3 ion recognition UV spectrum

[0049] Such as figure 1 As shown, it can be known that compound M3(10 -5 mol / L, with absolute ethanol as the solvent) the maximum absorption wavelength is 455nm. When M3 is mixed with other metal ions in an equivalent ratio of 1:1, only Fe 3+ The maximum absorption wavelength of the M3 solution is caused to shift right to 480nm, and the absorbance is obviously enhanced at the same time. At the same time, we use ion interference experiments to detect whether other metal ions will affect the M3 on Fe 3+ recognition, such as figure 2 As shown, the addition of other metal ions does not affect the M3-Fe 3+ The red shift of the mixed solution. This is consistent with the ion recognition pre-experimental results.

[0050] (2) Probe M3 ion recognition fluorescence spectrum

[0051] 10 with absolute ethanol as solvent -5 The metal ions of mol / L M3 were mixed according to the equivalent ratio of 1:1, and stood still for 30s; th...

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Abstract

The invention discloses a novel coumarin conjugated heterocyclic fluorescent probe for detecting Fe (III); phenanthroline is used as a receptor; coumarin with good photophysical and photochemical properties is used as a chromogenic group; the novel fluorescent probe 3-(2-(1,10-phenanthrolin-3-yl)ethynyl)-7-(diethylamino)-2H-coumarin (M3) is synthesized; the preparation method specifically comprises the step of synthesizing 3-bromo-7-diethylaminocoumarin, 3-(2-(trimethylsilyl)ethynyl)-1,10-phenanthroline, 3-ethynyl-1,10-phenanthroline and a phenanthrolinyl coumarin compound M3. The organic compound M3 has strong fluorescence, is a fluorescent probe capable of rapidly, efficiently and specifically identifying Fe<3+> in an aqueous solution, and has quite good application prospects, the synthesis process is simple, the reaction conditions are easy to control, and the yield is high.

Description

technical field [0001] The invention relates to a novel coumarin-based conjugated heterocyclic fluorescent probe for detecting Fe(III), specifically belonging to the technical field of organic synthesis. Background technique [0002] Iron (Ⅲ) plays a very important role in the normal work of the human physiological body. It is like hemoglobin transporting oxygen, but excessive iron (Ⅲ) content will cause serious physiological diseases in the human body, such as anemia. in Fe 3+ Among the detection methods, the fluorescence method has always been valued by researchers because of its good selectivity, high sensitivity, and easy operation. Although Fe 3+ Fluorescent probes have been researched and developed a lot, but they still have the following deficiencies: poor selectivity; low quantum yield; greatly affected by solvent or anion interference, etc. For example, in 2014, Olimpo García-Beltrán et al. synthesized two new coumarin-based fluorescent probes, BS1 and BS2, and s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C09K11/06G01N21/64
CPCC07D471/04C09K11/06G01N21/643C09K2211/1044C09K2211/1088G01N2021/6432
Inventor 胡斌朱琳杨习强罗旭彪颜流水邓春健
Owner NANCHANG HANGKONG UNIVERSITY
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