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Divalent copper ion fluorescent probe based on tetraphenylethylene ion complex and its preparation method and use

A technology of ion complexes and divalent copper ions, applied in the field of fluorescent probes, to achieve the effects of easy purification, simple operation and high yield

Inactive Publication Date: 2020-05-05
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the current research field, the detection of copper ions by AIE ion complexes has not been reported. Therefore, the construction of a new type of supramolecular AIE system through simple ion self-assembly can efficiently and quickly detect copper ions in theoretical research and practical applications. of great significance

Method used

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  • Divalent copper ion fluorescent probe based on tetraphenylethylene ion complex and its preparation method and use
  • Divalent copper ion fluorescent probe based on tetraphenylethylene ion complex and its preparation method and use
  • Divalent copper ion fluorescent probe based on tetraphenylethylene ion complex and its preparation method and use

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The preparation of compound (III), (document: Zhangwen Wei, Zhi-Yuan Gu, Ravi K.Arvapally, etal. J.Am.Chem.Soc.2014,136,8269-8276.) comprises the following steps:

[0048] (1)N 2 Under protection, 250ml of dry tetrahydrofuran (THF) was added to a 500ml two-neck flask, stirred at room temperature for 5min, 4.59g (0.07mol) of zinc powder was added, and 4.21ml (0.035mol) of titanium tetrachloride (TiCl 4 ), reflux at 75°C for 2h, cool to room temperature, add 20g of 4,4'-dibromobenzophenone, in N 2 During protection, react at 75°C for 24h to obtain a mixture. Mix the mixture, 20g of potassium carbonate, 20ml of deionized water and 120ml of dichloromethane thoroughly, then vacuum filter with diatomaceous earth, spin the obtained filtrate to remove the solvent, and wash the residue with dichloromethane and Methanol was recrystallized to remove unreacted monomers and purified to obtain tetra-(4-bromophenyl)ethylene (I).

[0049] (2) N Under protection, add tetrakis-(4-brom...

Embodiment 2

[0052] A preparation method of a divalent copper ion fluorescent probe based on tetraphenylethylene ion complex, comprising the steps of:

[0053] (1) 38 mg of compound (III) was dropped into 10 ml of potassium hydroxide (KOH) aqueous solution with a molar concentration of 0.023 mol / L, and stirred for 2 hours at 50° C. in a water bath to obtain a compound (IV) solution, which was cooled to room temperature; the compound The molar concentration of (III) is 0.0046mol / L, and the molar ratio of described potassium hydroxide and compound (III) is 5:1;

[0054] (2) 0.11g of the compound dioctadecyldimethylammonium bromide (DOAB) was dissolved in 16mL of 75% aqueous ethanol at 50°C to obtain a DOAB solution with a molar concentration of 0.011mol / L;

[0055] (3) Under the condition of stirring at 50°C, drop the compound (IV) solution into the solution obtained in step (2), stir, and a precipitate is formed, wash the precipitate with an aqueous ethanol solution with a volume concentrat...

Embodiment 3

[0060] A preparation method of a divalent copper ion fluorescent probe based on tetraphenylethylene ion complex, comprising the steps of:

[0061] (1) 55 mg of compound (III) was dropped into 15 ml of a molar concentration of 0.018 mol / L potassium hydroxide solution, and stirred for 3 hours at 45° C. in a water bath to obtain a solution of compound (IV), which was cooled to room temperature; the compound (III) The molar concentration is 0.006mol / L, and the mol ratio of described potassium hydroxide and compound (III) is 4:1;

[0062] (2) 0.156g compound dihexadecyldimethylammonium bromide (DHAB) was dissolved in 16mL of 40% ethanol aqueous solution at 45°C to obtain a DHAB solution with a molar concentration of 0.017mol / L;

[0063] (3) Under the condition of stirring at 45°C, drop the compound (IV) solution into the solution obtained in step (2), stir, and a precipitate is formed, wash the precipitate with an aqueous ethanol solution with a volume concentration of 40%, and dry...

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Abstract

The invention discloses a bivalent copper ion fluorescent probe based on a tetraphenyl vinyl ion complex and a preparation method and application. The probe is shown by a formula (V) as shown in the specification. The fluorescent probe is good in chemical stability, and has high solid fluorescence quantum yield. When the content of Cu2+ of a system is detected, the selectivity and the sensitivity can be high, and transient response can be achieved. In a certain copper ion concentration range, the fluorescence intensity changes linearly, and the calculated detection limit is 12.60 nM. Compared with the traditional fluorescent probe preparation method, the fluorescent probe has the advantages of simplicity in operation, high yield, easiness in purification, environmental protection and the like; and large-scale production and application are facilitated.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, in particular to a Cu 2+ Preparation method and application of fluorescent probe. Background technique [0002] Copper ions, as heavy metal ions, are necessary trace metal ions in animal and plant life systems, and the third most necessary trace elements after iron ions and zinc ions, and play an important role in the basic physiological processes of organisms. However, excessive intake of copper ions will have a negative effect on the living system and become a harmful substance in the organism. According to the regulations of the World Health Organization and the Environmental Protection Agency, the content of copper ions in drinking water should not exceed 2.0mg / L and 1.3mg / L respectively. If the human body ingests excessive copper ions, it will lead to the occurrence of neurological diseases, such as Alzheimer disease, amyotrophic lateral sclerosis, Menkes syndrome, etc.; excessi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C63/66C07C51/41C09K11/06C07C209/00C07C211/63G01N21/64
CPCC07C17/263C07C51/09C07C51/412C07C63/66C07C67/343C07C209/00C09K11/06C09K2211/1007G01N21/643C07C211/63C07C25/24C07C69/76
Inventor 任相魁路琳张磊冯亚凯郭锦棠
Owner TIANJIN UNIV
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