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Preparation and application of a mercury ion fluorescent probe compound based on rhodamine b

A technology for fluorescent probes and compounds, applied in the field of fluorescent probes, can solve the problems of inability to quantitatively measure mercury ion content, the probe does not provide a minimum detection limit, and it is difficult to meet low-concentration tests, and achieve good sensitivity and selectivity. , good promotion prospects, good water solubility

Inactive Publication Date: 2017-12-12
UNIV OF JINAN
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] In the prior art, CN104327843A provides a preparation method and application of a crown ether-based mercury ion fluorescent probe, which can be applied to the detection of mercury ions in water bodies, but it has the following disadvantages: 1. There are five steps in the preparation of the needle, and the synthetic route is lengthy; 2. The probe does not have an accurate working curve, and the content of mercury ions cannot be quantitatively determined; 3. The probe does not provide the lowest detection limit, which may be difficult to meet lower concentration test; 4. The excitation wavelength of the probe is 390 nm, which has a certain harmful effect on organisms; 5. The probe has not been applied to the detection of mercury ions in cells and cell imaging research
In addition, CN104151326A provides a method for preparing a mercury ion fluorescent probe based on perylene diimide-rhodamine B. The fluorescent probe has poor water solubility, and the solvent used is an aqueous solution containing 90% THF

Method used

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  • Preparation and application of a mercury ion fluorescent probe compound based on rhodamine b
  • Preparation and application of a mercury ion fluorescent probe compound based on rhodamine b
  • Preparation and application of a mercury ion fluorescent probe compound based on rhodamine b

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1. Synthesis of 6-methyl-2,2'-bipyridine ( figure 2 )

[0044] Put 5.30 g of 2,2'-bipyridine in a three-necked flask, protect with nitrogen and reduce to below 0℃ with an ice bath, then add 100 ml of dry ether to the flask until the 2,2'-bipyridine is completely dissolved; 26 ml (1.3 moles per liter) of methyl lithium was added dropwise to the flask, reacted for 2 hours in an ice bath and then heated to reflux for 3 hours. After cooling to room temperature, the reaction was quenched by adding 10 ml of water. After liquid separation, the aqueous phase was extracted with ether, the solvent was evaporated, 300 ml of saturated potassium permanganate in acetone was added, stirred for one hour, and the manganese dioxide was removed by filtration. The solvent was distilled off, and 3.728 g of pure product II was distilled under reduced pressure with a yield of 63.8%. NMR spectrum: 1 H NMR (400 MHz, CDCl 3 ) δ ppm: 8.65 (s, 1H), 8.38 (d, J = 8.10 Hz, 1H), 8.15 (d, J ...

Embodiment 2

[0045] Example 2. Synthesis of 6-aldehyde-2,2'-bipyridine ( image 3 )

[0046] Take 3.31 g of 6-methyl-2,2'-bipyridine, 3.24 g of selenium dioxide, and 0.21 ml of water, mix and dissolve in 50 ml of dioxane, heat to reflux for 3 hours, add 3.24 g of selenium dioxide and 0.21 ml of water, heated to reflux for 27 hours, after cooling to room temperature, the solvent was evaporated, methylene chloride:methanol=15:1 was used as a developing solvent, and the column was separated to obtain 1.28 g of pure product III with a yield of 31%. NMR spectrum: 1 H NMR (400 MHz, CDCl 3 ) δ ppm: 10.18 (s, 1H), 8.74(d, J = 4.83 Hz, 1H), 8.65 (dd, J = 7.12, 1.95 Hz, 1H), 8.56 (d, J = 7.95 Hz,1H), 7.97-8.02 (m, 2H), 7.90 (td, J = 7.65, 1.64 Hz, 1H), 7.40 (ddd, J =7.57, 4.87, 1.10 Hz, 1H).

Embodiment 3

[0047] Example 3. Synthesis of the fluorescent probe of the present invention ( Figure 4 )

[0048] Take 0.18 g of 6-aldehyde-2,2'-bipyridine and 0.55 g of rhodamine B hydrazide, dissolve it in 20 ml of ethanol, and heat to reflux for 6 hours. The product was separated with a basic silica gel column, and dichloromethane was used as a developing solvent to obtain 0.362 g of a pure product probe with a yield of 50%. NMR spectrum: 1 H NMR (400 MHz, CDCl 3 ) δ ppm :8.84 (s, 1H), 8.38 (d, J = 7.81Hz, 2H), 7.70-8.03 (m, 3H), 7.3-7.6 (m, 4H), 7.15 (d, J = 8.27 Hz, 1H), 6.55(t, J = 8.84 Hz, 1H), 6.46 (d, J = 2.12 Hz, 1H), 6.42 (dd, J = 7.81, 2.69 Hz, 2H), 6.25 (m, 2H), 3.33 (dt, J = 13.93, 7.17, 8H), 1.15 (dd, J = 12.72, 7.02Hz, 12H).

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Abstract

Provided are preparation and application of a mercury ion fluorescent probe compound based on rhodamine B. The invention relates to the mercury ion fluorescent probe compound and the preparation and the application thereof, wherein the mercury ion fluorescent probe compound has the structure represented by the formula I. The preparation method comprises the steps: carrying out a reaction of 2,2'-bipyridine with methyl lithium under the protection of nitrogen gas to obtain 6-methyl-2,2'-bipyridine, then oxidizing methyl by selenium dioxide to obtain 6-aldehyde-2,2'-bipyridine; and carrying out a reaction of 6-aldehyde-2,2'-bipyridine and rhodamine B hydrazide to obtain the final product probe molecule. The probe molecule has good selectivity and sensitivity to mercury ions, has no toxicity to cells, and not only can be used for detection of mercury ions in water bodies but also can be used for detection and imaging of mercury ions in cells.

Description

Technical field [0001] The invention relates to a mercury ion fluorescent probe compound and its preparation and application, belonging to the technical field of fluorescent probes. technical background [0002] Mercury is a heavy metal element that exists widely in nature, and it is also one of the heavy metal elements that damage the human body the most. It can be enriched in animals and plants and enter the human body through the food chain. In the human body, non-polar mercury ions can be converted into more toxic organic mercury by bacteria, and eventually cause systemic poisoning. For example, after methylmercury enters the human body, it often causes specific and selective damage to the brain nerves, which can lead to behavioral disorders and nerve damage. The'Minamata disease' that occurred in Japan was caused by methylmercury poisoning. However, industrial projects such as salt electrolysis and precious metal smelting often involve the application of mercury metal. T...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/643G01N21/6486
Inventor 范春华黄曦明吕正亮
Owner UNIV OF JINAN
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