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Hemicyanine-based copper ion ratiometric fluorescent probe and preparation and application thereof

A ratio fluorescent probe, copper ion technology, applied in the field of copper ion ratio fluorescent probe, to achieve the effect of simple post-processing, high selectivity and sensitivity

Active Publication Date: 2017-08-11
HEZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • Hemicyanine-based copper ion ratiometric fluorescent probe and preparation and application thereof
  • Hemicyanine-based copper ion ratiometric fluorescent probe and preparation and application thereof
  • Hemicyanine-based copper ion ratiometric fluorescent probe and preparation and application thereof

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Embodiment

[0043] (1) Preparation of the target compound copper ion fluorescent probe

[0044] (1) Synthesis of compound 1

[0045]

[0046] Dissolve 4-picoline (1.96ml, 20mmol) and methyl iodide (1.56ml, 25mmol) in acetonitrile (20ml), heat and reflux for 10 hours under the protection of argon. After the reaction is complete, cool to room temperature, there is a solid It separated out, filtered and washed with ethyl acetate, and collected the solid with a yield of 88%.

[0047] (2) Synthesis of compound 2

[0048]

[0049] Compound 1 (2.35g, 10mmol), 4-hydroxybenzaldehyde (1.83g, 15mmol) and piperidine (0.5mL, 5mmol) were dissolved in absolute ethanol (30mL), and heated and refluxed for 10 hours under the protection of argon. After the reaction is completed, it is cooled to room temperature, and a solid is precipitated. The solid is filtered and washed with absolute ethanol to collect the solid. The yield is 80%.

[0050] Compound 2 1 The H NMR spectrum is as figure 1 As shown, 1 H NMR(400MHz,...

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Abstract

The invention relates to a hemicyanine-based copper ion ratiometric fluorescent probe and preparation and application thereof. The molecular formula of the fluorescent probe is C20H17IN2O2; the preparation of the fluorescent probe comprises the steps that 1, 4-picoline and iodomethane react to obtain 1,4-lutidine iodate which is a compound 1; 2, the compound 1 and 4-hydroxybenzaldehyde react to obtain 4-(4-hydroxyl-styryl)-1-picoline iodate which is a compound 2; 3, the compound 2 and 2-picolinic acid react to obtain a copper ion ratiometric fluorescent probe 4-(4-picolinate-styryl)-1-picoline iodate which is a compound 3. According to the application of the fluorescent probe, the fluorescent probe and copper ions react in a pure water solution, and changes of the ratio (F503 nm / F448 nm) of fluorescence intensities at two different emission wavelengths are used for detecting whether copper ions exist or not. The probe is simple in preparation and treatment process, molecules of the fluorescent probe are in a copper ion and other positive ion coexistence system, and the high selectivity and sensitivity are shown.

Description

Technical field [0001] The invention belongs to the technical field of fluorescent probes for detecting metal ions, and specifically relates to a hemicyanine-based copper ion ratio fluorescent probe and its preparation and application. Background technique [0002] Copper ion (Cu 2+ ) Is the third most abundant element in the human body, and it plays an important role in various basic physiological processes of the organism, such as gene expression and signal transduction. But Cu in the cell 2+ Variations in the concentration can cause various diseases, including Alzheimer's disease, Menkes syndrome, Wilsons disease, and even cancer. In addition, Cu 2+ It is widely used in industry and agriculture, so it is also a serious environmental pollutant. Therefore, looking for a simple and fast detection method for Cu 2+ Analysis and testing are of great significance. Existing Cu 2+ The main methods are atomic absorption spectrometry and spectrophotometry, but the former requires compl...

Claims

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Application Information

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IPC IPC(8): C07D213/79C07D213/803C09K11/06G01N21/64
CPCC07D213/79C07D213/803C09K11/06C09K2211/1029G01N21/6428
Inventor 朱东建钟星任爱山胡彩霞段振华严小威王素娟帅良
Owner HEZHOU UNIV
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