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Near-infrared fluorescent compound, preparation method and application thereof in detection of ferrous ions

A fluorescent compound, near-infrared technology, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the problems that the emission wavelength is less reachable, easily interfered by other metal ions, etc., to avoid interference and simple preparation. , selective effect

Active Publication Date: 2019-12-13
SHANDONG NORMAL UNIV
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  • Abstract
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  • Application Information

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Problems solved by technology

[0004] As far as the inventors of the present disclosure know, current methods for detecting ferrous ions include spectroscopic methods, electrochemical methods, and fluorescence methods, among which, the fluorescence method has the advantages of high selectivity, low toxicity, and ease of use, and has been widely used in biological analysis. application; however, the inventors of the present disclosure found in research that the existing detection of Fe 2+ The fluorescent probes have the problems that the maximum excitation and emission wavelengths rarely reach the near-infrared region, and are easily interfered by other metal ions.

Method used

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  • Near-infrared fluorescent compound, preparation method and application thereof in detection of ferrous ions
  • Near-infrared fluorescent compound, preparation method and application thereof in detection of ferrous ions
  • Near-infrared fluorescent compound, preparation method and application thereof in detection of ferrous ions

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preparation example Construction

[0030] Another embodiment of the present disclosure provides a method for preparing the above-mentioned near-infrared fluorescent compound, which includes the following reaction route to prepare the near-infrared fluorescent compound:

[0031]

[0032] In one or more examples of this embodiment, compound 1 is subjected to a substitution reaction with tert-butyl bromoacetate to obtain compound 2, and compound 2 is subjected to a substitution reaction with 2,6-dibromomethylpyridine to obtain compound 3,4-hydroxy The etherification reaction between isophthalaldehyde and compound 3 obtains compound 4, and the condensation reaction of compound 4 and 2 equivalents of 1,2,3,3-tetramethyl-3H-indole iodide obtains compound 5, and the desorption of compound 5 The near-infrared fluorescent compound was obtained by removing the tert-butyl protecting group.

[0033] In this series of examples, the conditions for the etherification reaction are: adding cesium carbonate and heating to 75-...

Embodiment 1

[0044] Synthesis of fluorescent probes:

[0045] Dissolve di-2-pyridyl ketone (0.744, 3.9 mmol) and hydroxylamine hydrochloride (0.39, 6.06 mmol) in 9 mL of absolute ethanol, stir at room temperature for 90 min, slowly add sodium hydroxide (0.78 g, 19.98 mmol) and heat Reflux at 80°C for 10 min, during which time the solution turns dark orange and a white precipitate forms. The reaction mixture was treated with water (60 mL) and concentrated hydrochloric acid (30 mL), and ethanol was removed by rotary evaporation to give a dark red solution. The product was precipitated by the addition of saturated aqueous sodium carbonate (60 mL) and isolated by vacuum filtration, washed with water, and dried under vacuum at room temperature to give the product bis-2-pyridylketoxime as a white solid.

[0046] The chemical route is as follows:

[0047]

[0048] In 8.5mL ethanol, 5mL water and 7.5mL 23% ammonia water, add bis-2-pyridyl ketoxime (0.5g, 2.5mmol) and ammonium acetate (0.33g, 4....

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Abstract

The invention provides a near-infrared fluorescent compound, a preparation method and application of the near-infrared fluorescent compound in detection of ferrous ions. The near-infrared fluorescentcompound provided by the invention can enable a fluorescence probe of Fe < 2 + > to have a maximum excitation emission wavelength reaching a near-infrared region, and has good selectivity to the Fe <2 + >.

Description

technical field [0001] The disclosure relates to a near-infrared fluorescent compound, a preparation method and an application for detecting ferrous ions. Background technique [0002] The statements herein merely provide background information related to the present disclosure and may not necessarily constitute prior art. [0003] Iron is an essential metal element to maintain normal life activities of the human body, and plays an important role in cellular functions such as oxygen operation and DNA synthesis. However, excessive iron will increase the generation of reactive oxygen species ROS, damage cell membranes, proteins and DNA, and lead to apoptosis, and iron overload is directly related to the induction of diseases such as thalassemia and Friedrich's ataxia. In addition, since transferrin and ferritin, which are involved in iron metabolism, are synthesized in the liver, the liver becomes the primary organ damaged by iron overload. A large number of studies have show...

Claims

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Application Information

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IPC IPC(8): C07D401/14C09K11/06G01N21/64
CPCC07D401/14C09K11/06C09K2211/1007C09K2211/1029G01N21/643Y02P20/55
Inventor 唐波李平吴丽杰范楠楠
Owner SHANDONG NORMAL UNIV
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