Malononitrile isophorone copper ion fluorescent probe and preparation method thereof

A technology of malononitrile isophorone and fluorescent probe, which is applied in the field of analysis and detection, can solve the problems of low copper ion selectivity and sensitivity, and achieve the effects of easy monitoring and control, easy separation, and easy access to raw materials

Inactive Publication Date: 2015-08-26
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There are many defects in the copper ion fluorescent probes reported in recent years, for example, copper ions can only be detected in pure organic solvent systems or solvent systems with low water content (G. Ajayakumar, K. Sreenath, K. R. Gopidas, Phenothiazine attached Ru(bpy) 3 2+ derivative as highly selective "turn-ON" luminescence chemodosimeter for Cu 2+ , Dalton Trans., 7 (2009) 1180-1186); special reaction conditions are required (N. Li, Y. Xiang, A. J. Tong, Highly sensitive and selective "turn-on" fluorescent chemosimeter for Cu 2+ in water via Cu 2+ -promoted hydrolysis o

Method used

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  • Malononitrile isophorone copper ion fluorescent probe and preparation method thereof
  • Malononitrile isophorone copper ion fluorescent probe and preparation method thereof
  • Malononitrile isophorone copper ion fluorescent probe and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Synthesis of Copper Ion Fluorescent Probe Compounds Based on Malononitrile Isophorone

[0032] In a 50 mL one-necked flask, 2-[3-(4-hydroxystyryl)-5,5-dimethyl-cyclohex-2-en-1-ylidene]malononitrile (300 mg, 1.0 mmol), 2-pyridinecarboxylic acid (191 mg, 1.3 mmol), 4-dimethylaminopyridine (76 mg, 0.6 mmol) and dicyclohexylcarbodiimide (320 mg, 1.6 mmol) were dissolved in 10 mL of dry THF , stirred and reacted at room temperature for 10 h, filtered, the filtrate was decompressed to remove the solvent, the resulting residue was dissolved in dichloromethane, the dichloromethane solution was washed with 1% dilute hydrochloric acid, dried over anhydrous sodium sulfate, and the solvent was evaporated to dryness under reduced pressure to obtain the crude product , recrystallized from a dichloromethane / petroleum ether mixed solution to obtain yellow crystals with a yield of 60%.

[0033] Among them, 2-[3-(4-hydroxystyryl)-5,5-dimethyl-cyclohex-2-en-1-ylidene] malononitrile can b...

Embodiment 2

[0036] Synthesis of Copper Ion Fluorescent Probe Compounds Based on Malononitrile Isophorone

[0037] In a 50 mL one-necked flask, 2-[3-(4-hydroxystyryl)-5,5-dimethyl-cyclohex-2-en-1-ylidene]malononitrile (300 mg, 1.0 mmol), 2-pyridinecarboxylic acid (220 mg, 1.5 mmol), 4-dimethylaminopyridine (76 mg, 0.6 mmol) and dicyclohexylcarbodiimide (360 mg, 1.8 mmol) were dissolved in 10 mL of dry tetrahydrofuran , stirred at room temperature for 7 h, filtered, the filtrate was removed from the solvent under reduced pressure, the resulting residue was dissolved in dichloromethane, the dichloromethane solution was washed with 1% dilute hydrochloric acid, dried over anhydrous sodium sulfate, and the solvent was evaporated to dryness under reduced pressure to obtain the crude product , recrystallized from a dichloromethane / petroleum ether mixed solution to obtain yellow crystals with a yield of 56%.

Embodiment 3

[0039] Synthesis of Copper Ion Fluorescent Probe Compounds Based on Malononitrile Isophorone

[0040] In a 50 mL one-necked flask, 2-[3-(4-hydroxystyryl)-5,5-dimethyl-cyclohex-2-en-1-ylidene]malononitrile (300 mg, 1.0 mmol), 2-pyridinecarboxylic acid (147 mg, 1.0 mmol), 4-dimethylaminopyridine (76 mg, 0.6 mmol) and dicyclohexylcarbodiimide (200 mg, 1.0 mmol) were dissolved in 10 mL of dry tetrahydrofuran , stirred at room temperature for 14 h, filtered, the filtrate was decompressed to remove the solvent, the resulting residue was dissolved in dichloromethane, the dichloromethane solution was washed with 1% dilute hydrochloric acid, dried over anhydrous sodium sulfate, and the solvent was evaporated to dryness under reduced pressure to obtain the crude product , recrystallized from a dichloromethane / petroleum ether mixed solution to obtain yellow crystals with a yield of 54.5%.

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Abstract

The invention discloses a malononitrile isophorone copper ion fluorescent probe and a preparation method thereof, and relates to the technical field of analysis and detection. The malononitrile isophorone copper ion fluorescent probe has good fluorescence property, and assists in selectively identifying copper ions in a buffering solution. The fluorescent probe has the advantages of low detection limit (only 0.2 muM), large Stokes shift, fluorescence enhancement, long-wavelength emission and visible-light discoloration. Copper ion naked eye detection can be realized with the fluorescence enhancement and visible-light discoloration properties. With the fluorescence enhancement response of the probe upon copper ions, the copper ions can be subjected to qualitative or quantitative analyses. The probe can enter HeLa cells and can show a red fluorescence image after a reaction with copper ions in the cells. Therefore, the copper ion fluorescent probe provided by the invention can be sued in copper ion detections of the environment and in biological cells.

Description

technical field [0001] The invention relates to the technical field of analysis and detection, in particular to a malononitrile isophorone-based copper ion fluorescent probe and a preparation method thereof. Background technique [0002] Copper is the third transition metal element necessary for the human body and plays an important physiological role in many biological life systems. A lack of copper ions in the human body can lead to neurodegenerative diseases such as Alzheimer's disease, Menkes syndrome, Wilson's disease and Prion's disease. Excessive intake of copper ions by the human body will react with oxygen molecules to generate active oxygen species, which will damage proteins, nucleic acids and lipids. In addition, due to the extensive use of copper in industry and life, it also causes serious pollution to the environment. Therefore, the ability to detect copper ions in organisms and in the environment with high sensitivity and high selectivity has attracted more...

Claims

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Application Information

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IPC IPC(8): C07D213/79C07D213/803G01N21/64C09K11/06
CPCC07D213/79C07D213/803C09K11/06C09K2211/1029G01N21/64G01N21/6447G01N21/6486
Inventor 张大同安瑞冰
Owner QILU UNIV OF TECH
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