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Synthesis and application of fluorescence enhancement detection mercury ion probe

A fluorescent molecular probe and fluorescent probe technology, applied in the field of chemical analysis and detection, can solve the problems of poor selectivity, easy to be interfered by other ions, etc., and achieve the effects of high synthesis yield, high sensitivity and fast response speed.

Inactive Publication Date: 2013-08-14
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to the reaction mechanism of mercury ion fluorescent probes, it can be divided into two categories: one is the use of complex coordination between mercury ions and some heteroatoms. Mercury ion probes based on this mechanism usually have better sensitivity, and Fast response time; however, it is also less selective and often susceptible to interference from other ions

Method used

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  • Synthesis and application of fluorescence enhancement detection mercury ion probe
  • Synthesis and application of fluorescence enhancement detection mercury ion probe
  • Synthesis and application of fluorescence enhancement detection mercury ion probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the preparation of 2-(2-bromoethoxy)-4-diethylaminobenzaldehyde

[0034] 4-Diethylamino salicylaldehyde (0.965g, 5mmol), potassium carbonate (1.383g, 20mmol) and 1,2-dibromoethane (9.4g, 50mmol) were added to 15mL of acetonitrile, and heated to reflux for 48h , cooled to room temperature, filtered to remove K 2 CO 3 , washed with acetonitrile, distilled off the solvent, and separated by column chromatography (petroleum ether at a volume ratio of 6:1: ethyl acetate was the eluent) to obtain 0.780 g (yield: 52%) of a pale yellow solid, namely 2- (2-Bromoethoxy)-4-diethylaminobenzaldehyde.

Embodiment 2

[0035] Embodiment 2: Preparation of 2-vinyloxy-4-diethylaminobenzaldehyde

[0036] Dissolve 2-(2-bromoethoxy)-4-diethylaminobenzaldehyde (300 mg, 1 mmol) in 10 mL of dry dimethyl sulfoxide, add potassium tert-butoxide (128 mg, 1.1 mmol) at 25 ° C The mixture was stirred for 4 hours and the progress of the reaction was monitored by thin layer chromatography. After the reaction, the reaction solution was poured into 70 mL of water, extracted twice with ethyl acetate (2×75 mL), the organic layer was separated, and washed with saturated ammonium chloride solution and saturated brine, respectively. The organic phase was separated and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and separated by column chromatography (petroleum ether:ethyl acetate at a volume ratio of 6:1 as eluent) to obtain 0.103 g (yield: 47%) of a light yellow oily liquid, which was 2-ethyleneoxy -4-Diethylaminobenzaldehyde.

Embodiment 3

[0037] Embodiment 3: Preparation of molecular fluorescent probe

[0038] Dissolve 2-vinyloxy-4-diethylaminobenzaldehyde (123 mg, 0.561 mmol) and malononitrile (75 mg, 1.137 mmol) in 7 mL of absolute ethanol, add piperidine (20 μL, 0.202 mmol), and After stirring for 5 hours, a light yellow solid was precipitated, which was filtered by suction and dried in air to obtain 113.8 mg of the product (yield: 72.09%), which was the probe molecule.

[0039] HNMR (400MHz, CDCl 3 ):δ ppm = 1.33 (6H, t, J = 8Hz), 3.47 (4H, q, J = 8Hz), 4.65 (1H, dd, J = 4, 1.6Hz), 4.92 (1H, dd, J = 1.6, 1.6Hz) , 6.22 (1H, d, J = 2.4Hz), 6.66 (1H, dd, J = 2.4, 2.4Hz), 6.95 (1H, dd, J = 6, 5.6Hz), 7.09 (1H, s), 8.06 ( 1H, d, J=9.6Hz).

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Abstract

The invention relates to a preparation method and application of a fluorescence enhancement type mercury ion probe, and particularly relates to preparation based on 2-(2-ethyleneoxy-4-dialkyl amino-benzylidene)-malononitrile and high-sensitivity detection applied to mercury ions. The fluorescent probe disclosed by the invention has the advantages of easiness and convenience for synthesis, moderate reaction condition, easiness for purification, high synthesis yield, better water solubility, higher selectivity and stability in optical property. According to the invention, the maximum absorption wavelength of a probe molecule in a PBS (Phosphate Buffer Solution) (pH=7.4) and DMSO (Dimethylsulfoxide) mixed solution (with the volume ratio of 95:5) is 446 nanometers, and the fluorescent light is very weak; the absorption wavelength is removed from 446 nanometers to 437 nanometers with the addition of the mercury ions; and the intensity of a fluorescence spectrum is continuously enhanced on a position with the wavelength of 486 nanometers, and the maximum enhancement is 90 times. The fluorescent probe molecule is very suitable for being applied to an organism and has important practical application value in the fields of biology, medical chemistry, environmental science, and the like.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a preparation method of a fluorescence-enhanced fluorescent molecular probe for detecting mercury ions and the application of the fluorescent molecule in detecting mercury ions. Background technique [0002] Mercury is a highly toxic heavy metal ion that is quite common in environmental pollution. For example, mercury is widely present in solid waste, factory sewage, mine wastewater and other environmental pollution. In nature, mercury ions will be absorbed by various animals and plants and introduced into the human body through the food chain, causing a series of harmful effects on human health. Such as brain damage, kidney failure, nervous system and immune system damage. Although mercury ions will have adverse effects on environmental protection and human health, it is still widely used in industrial production processes. Therefore, it is very necessa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/37C09K11/06G01N21/64C07C253/30
Inventor 宋相志刘倩
Owner CENT SOUTH UNIV
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