Near-infrared fluorescent probe compound taking N-pyridine oxide derivative as recognition group as well as preparation and application of near-infrared fluorescent probe compound

A pyridine oxide and fluorescent probe technology, which is applied in the field of preparation and application of new recognition groups, can solve problems such as uncertainty and unexpectedness, and achieve the effects of easy preparation, easy availability of raw materials, and simple synthesis steps.

Active Publication Date: 2021-06-11
GUANGZHOU YUEWANG AGRI CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After the identification cavity is constructed, it is uncertain what kind of metal ion will be identified, and it can only be confirmed after a large number of screenings, which is unexpected

Method used

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  • Near-infrared fluorescent probe compound taking N-pyridine oxide derivative as recognition group as well as preparation and application of near-infrared fluorescent probe compound
  • Near-infrared fluorescent probe compound taking N-pyridine oxide derivative as recognition group as well as preparation and application of near-infrared fluorescent probe compound
  • Near-infrared fluorescent probe compound taking N-pyridine oxide derivative as recognition group as well as preparation and application of near-infrared fluorescent probe compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Dissolve pyridinemethanol N-oxide (3.0g, 24.0mmol) in 10mL of pyridine solution, add selenium dioxide (3.20g, 28.8mmol) in batches while stirring, then heat to 90°C and reflux for 3h to stop the reaction. Suction filtration, the filter cake was washed with a small amount of dichloromethane, and the filtrate was concentrated to obtain the crude product of pyridine formaldehyde N-oxide, which was recrystallized from a mixed solvent of petroleum ether and ethyl acetate (60mL, V / V=5:1) to obtain the pure product , (2.30 g, 77.8% yield).

Embodiment 2

[0036] In a 100mL single-necked round bottom flask, add rhodamine B (2.9g, 6.0mmol), absolute ethanol (50mL) and 85% hydrazine hydrate (10mL) successively, and mix and reflux at 78°C for 12 hours, and the solution changes from dark purple to Bright yellow, and finally turned into a transparent and clear solution. After the reaction was completed, it was cooled, and the solvent was removed under reduced pressure to obtain a viscous solid. Add 10mL concentrated hydrochloric acid (1mol / L) dropwise to the above solid to obtain a red clear solution, then gradually add 1mol / L sodium hydroxide aqueous solution dropwise, adjust the pH value of the solution to 9, a large amount of precipitation occurs, filter, and deionized water The filter cake was washed and vacuum-dried to obtain rhodamine B hydrazide dyes (2.10 g, yield 76.6%).

Embodiment 3

[0038]Rhodamine B hydrazide dye (0.92g, 2.0mmol) was added to 20mL of ethanol, after it was completely dissolved, N-oxypyridineformaldehyde (0.246g, 2.0mmol) was added, and the mixture was refluxed at 80°C for 12h under the protection of nitrogen. , cooled, removed the solvent under reduced pressure, then extracted with ethyl acetate, distilled off the ethyl acetate at 45-55°C, separated by silica gel column chromatography, and the eluent was dichloromethane / methanol (V / V=30:1), to obtain The yellow solid (0.629 g, yield 56%) is the N-oxide pyridine-rhodamine B-type near-infrared fluorescent probe (RhBF). like Figure 5 , Image 6 and Figure 7 Shown, ESI mass spectrum: m / z[M+H] + 562.2799. 1 H NMR (500MHz, CD 3 Cl) δ (ppm): 1.15 (t, 12H, J = 7.0Hz), 3.32 (q, 8H, J = 7.0Hz), 6.23-6.25 (m, 2H), 6.46-6.49 (m, 4H), 7.06 -7.13(m,3H),7.46-7.54(m,2H),7.86(dd,1H,J=7.0Hz,J=2.0Hz),7.99-8.02(m,2H),9.12(s,1H); 13 C NMR (125MHz, CD 3 Cl)δ (ppm): 12.6, 44.3, 66.3, 98.1, 105.3, 107....

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Abstract

The invention discloses a near-infrared fluorescent probe compound taking an N-pyridine oxide derivative as a recognition group as well as preparation and application of the near-infrared fluorescent probe compound. The preparation method specifically comprises the following steps: firstly, oxidizing a pyridine heterocyclic compound into an N-pyridine-2-formaldehyde oxide derivative, and taking the N-pyridine-2-formaldehyde oxide derivative as a recognition group; finally, enabling rhodamine B hydrazide to react with the N-pyridine oxide derivative in an organic solvent, so as to obtain the N-pyridine oxide-rhodamine B near-infrared fluorescent probe. The N-pyridine oxide-rhodamine B type near-infrared fluorescent probe can detect divalent palladium ions with high sensitivity and high selectivity, can realize colorimetric and fluorescent dual-mode detection of the divalent palladium ions in the environment, and can also be used for rapid detection of the divalent palladium ions in cells. Besides, the applied N-pyridine oxide derivative is a new recognition group which is easily available in initial raw material and easy to prepare, and has a wide application prospect in the aspect of detecting other heavy metal ions after being combined with other common dyes.

Description

technical field [0001] The invention belongs to an ion detection fluorescent probe compound and its preparation method and application, in particular to the preparation and application of a new recognition group, and belongs to the technical field of organic synthesis and analytical chemistry. Background technique [0002] Palladium metal is called the "vitamin" of modern industry, and it is an indispensable raw material for high-tech fields such as aerospace, aviation, navigation, weapons and nuclear energy, as well as automobile manufacturing. Divalent palladium ions are widely used in electroplating, industrial catalysis, preparation of fine chemicals and drug molecules. Fuel cells, hydrogen storage materials, dental crown materials, medical devices, etc. will also produce a large amount of divalent palladium ions. With the continuous increase of the demand for divalent palladium ions, serious environmental pollution problems have been caused. After animals and plants a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06G01N21/6428G01N21/643C09K2211/1029C09K2211/1033G01N2021/6439
Inventor 张向阳
Owner GUANGZHOU YUEWANG AGRI CO LTD
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