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Pyridazino quinoxaline diamine Schiff base cobalt ion fluorescent probe and preparation method thereof

A technology of quinoxaline diamine Schiff base cobalt and fluorescent probes, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, and can solve problems such as single detection mode, inability to perform quantitative detection, and detection effect interference

Active Publication Date: 2020-10-23
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The detection effect of these fluorescent probes is not only susceptible to interference from external factors such as competing ions, reaction time, and pH range, but also has a single detection mode, which is sensitive to different concentrations of Co 2+ Quantitative detection is not possible

Method used

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  • Pyridazino quinoxaline diamine Schiff base cobalt ion fluorescent probe and preparation method thereof
  • Pyridazino quinoxaline diamine Schiff base cobalt ion fluorescent probe and preparation method thereof
  • Pyridazino quinoxaline diamine Schiff base cobalt ion fluorescent probe and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0030] Preparation of 6,11,11-trimethyl-6,7,8,9-tetrahydro-6,9-methanopyridazino[4,5-b]quinoxaline-1,4- from camphorquinone The reaction formula of diamine condensation 2-hydroxyl-1-naphthaldehyde bis-Schiff base is:

[0031]

[0032]

[0033] Specific steps are as follows:

[0034] 1) Preparation of 5,9,9-trimethyl-5,6,7,8-tetrahydro-5,8-methanoquinoline-2,3-dicarbonitrile:

[0035] Add 0.9mmol camphorquinone, 1mmol 2,3-diaminomaleonitrile, and 7mL acetic acid to a dry three-necked flask in turn, reflux for 4 hours, track and monitor with TLC, stop the reaction after the reaction is complete; the reaction solution is decompressed After distilling off acetic acid, dichloromethane was added, washed with saturated brine until neutral, and the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to obtain 5,9,9-trimethyl-5,6,7 , 8-tetrahydro-5,8-methanoquinoline-2,3-dicarbonitrile crude product; 5,9,9-trimethyl-5,6,7,8-tetrahydro-5, The crude p...

Embodiment 2

[0041] 6,11,11-trimethyl-6,7,8,9-tetrahydro-6,9-methanopyridazino[4,5-b]quinoxaline-1,4-diamine 2-Hydroxy-1-naphthaldehyde bis-Schiff base was dissolved in PBS / THF (v / v=6 / 4) buffer to prepare 0.5×10 -5 M concentration of the probe solution, the CoCl 2 ·6H 2 O was dissolved in PBS / THF (v / v=6 / 4) buffer to prepare solutions with concentrations of 0, 2.0, 4.0, 6.0, 8.0, 10.0, 12.0, 14.0, 16.0, 18.0, and 20.0 μM. Using the standard titration method to measure the cobalt ion of different concentrations under the fluorescence spectrophotometer 6,11,11-trimethyl-6,7,8,9-tetrahydro-6,9-endomethylene pyridazino The fluorescence emission spectrum of [4,5-b]quinoxaline-1,4-diamine condensed 2-hydroxyl-1-naphthaldehyde bis-Schiff base, such as figure 1 shown. The results showed that in the concentration range of 0-20μM, with the continuous increase of cobalt ion concentration in the system, the orange-yellow fluorescence of the solution was quenched, which indicated that the probe coul...

Embodiment 3

[0043] 6,11,11-trimethyl-6,7,8,9-tetrahydro-6,9-methanopyridazino[4,5-b]quinoxaline-1,4-diamine 2-Hydroxy-1-naphthaldehyde bis-Schiff base was dissolved in PBS / THF (v / v=6 / 4) buffer to prepare 0.5×10 -5 For the probe solution of M concentration, various metal salt compounds were dissolved in PBS / THF (v / v=6 / 4) buffer solution to prepare 1.0×10 -4 M concentration of metal ion solution (Co 2+ , K + , Na + , Ca 2+ , Zn 2+ , Fe 3+ , Fe 2+ , Sn 2+ , Cr 2+ , Cs + , Ni 2+ , Ce 4+ , La 3+ , Al 3+ , Cu 2 + , Ag + , Mg 2+ , Mn 2+ , Hg 2+ , Pb 2+ , Cd 2+ ). Different ion pairs of 6,11,11-trimethyl-6,7,8,9-tetrahydro-6,9-methanopyridazino[4 , 5-b] the fluorescence emission spectrum of quinoxaline-1,4-diamine condensation 2-hydroxyl-1-naphthaldehyde bis-Schiff base, such as figure 2 shown. The results showed that the fluorescence was obviously quenched after adding cobalt ions in the probe solution, while adding other ions such as K + , Na + , Ca 2+ , Zn 2+ , Fe...

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Abstract

The invention discloses a pyridazino quinoxaline diamine Schiff base cobalt ion fluorescent probe and a preparation method thereof. The preparation method comprises the following steps: taking a camphor derivative camphorquinone as a raw material, and carrying out cyclization reaction on the camphor derivative camphorquinone and 2, 3-diaminomaleonitrile to obtain 5, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-bridge methylene quinoline-2, 3-dicarbonitrile; carrying out condensation cyclization with hydrazine hydrate to obtain 6, 11, 11-trimethyl-6, 7, 8, 9-tetrahydro-6, 9-bridged methylene pyridazino [4, 5-b] quinoxaline-1, 4-diamine; carrying out condensation reaction with 2-hydroxyl-1-naphthaldehyde to obtain 6, 11, 11-trimethyl-6, 7, 8, 9-tetrahydro-6, 9-bridge methylene pyridazino [4, 5-b] quinoxaline-1, 4-diamine condensed 2-hydroxyl-1-naphthaldehyde bis-schiff base. The compound can be quickly and specifically complexed with Co < 2 + > at room temperature, so that orange-yellow fluorescence of a solution is quenched, the color of the solution is changed from orange red to dark red under sunlight, and the compound can be used as a fluorescent probe for detecting cobalt ions andhas a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a pyridazinoquinoxaline diamine Schiff base cobalt ion fluorescent probe and a preparation method thereof. Background technique [0002] Cobalt is an essential trace element for the human body. Its physiological function mainly involves the composition of vitamin B12, which is necessary for the formation of red blood cells. Cobalt deficiency can lead to pernicious anemia, but excessive intake can lead to polycythemia, or excess red blood cells, and heart disease. Long-term inhalation of dust or smoke can affect lung function and cause lung diseases such as diffuse nodular fibrosis. Cobalt may cause memory deficits in humans and has been reported to cause neurotoxicity in animal models. Skin contact can cause allergic skin reactions, resulting in atopic dermatitis. According to reports, Co. 2+ Ions are genotoxic both in vitro and in vivo, and are carcinogenic. I...

Claims

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Application Information

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IPC IPC(8): C07D487/08C09K11/06G01N21/64
CPCC07D487/08C09K11/06G01N21/6428C09K2211/1074G01N2021/6432
Inventor 王石发刘豪闯杨海燕王忠龙李明新张燕杨益琴徐徐
Owner NANJING FORESTRY UNIV
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