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A probe for detecting copper ions and zinc ions, its preparation method and application

A carbon atom and carbon number technology, which is applied in the field of molecular probes for selective detection of copper ions and zinc ions and their preparation, can solve the problems of detecting interference of cadmium ions, difficult to apply zinc ion detection, etc., and achieves easy preparation and production. High rate and fast response effect

Active Publication Date: 2019-04-12
东营睿港投资服务有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

3d due to zinc ions 10 4s 0 The electronic structure of Zn has no measurable spectrum and NMR signals, so commonly used detection methods such as ultraviolet spectroscopy, nuclear magnetic resonance, electron paramagnetic resonance, etc. are difficult to apply to the detection of zinc ions
Most of the existing zinc ion detection methods are based on fluorescent probe methods, but the detection process is easily interfered by cadmium ions

Method used

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  • A probe for detecting copper ions and zinc ions, its preparation method and application
  • A probe for detecting copper ions and zinc ions, its preparation method and application
  • A probe for detecting copper ions and zinc ions, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of compound DC-1 with R=n-butyl

[0030]

[0031] (1) In a 100mL single-neck flask, add 0.46g (19.2mmol) of sodium hydride, then add 50mL of DMF as a solvent, add 1g (2.77mmol) of compound a under ice bath, stir for 0.5h and then add chloromethyl methyl ether dropwise 0.9 mL (11.85 mmol), stirred at room temperature for 2 hours after the addition was completed, and filtered with suction to obtain compound b with a yield of 95%.

[0032] (2) After adding 0.5 g (1.11 mmol) of compound b into a 50 mL two-neck flask, adding 25 mL of isopropyl ether as a solvent, and stirring with argon for 5 minutes under ice bath. Add 0.84mL (5.47mmol) of tetramethylethylenediamine under the protection of argon, then add 3.12mL (5.0mmol) of 1.6M n-butyllithium dropwise, stir for 2 hours in an ice bath and 2 hours at room temperature, then under an ice bath Add 0.77 mL (9.99 mmol) of DMF, continue to stir in an ice bath for 2 hours, add 7 mL of saturated ammonium chloride to quench ...

Embodiment 2

[0038] Preparation of compound DC-2 with R=cyclohexyl

[0039]

[0040] (1) Preparation of compound d According to the preparation method in Example 1.

[0041] (2) Compound d (416mg, 1mmol) was dissolved in 5mL ethanol, and cyclohexylamine (2mmol) was slowly added. After the addition was completed, reflux for 2 hours. A precipitate precipitated. Cool, filter the solid, and wash with ice ethanol, and dry the solid in vacuo Compound DC-2 was obtained with a yield of 92%.

[0042] Test results: 1 H NMR(500MHz, CDCl 3 )δ13.08(s,2H),8.66(dd,J=5.7,3.2Hz,2H),8.55(s,2H),8.47(d,J=8.8Hz,2H),7.95(d,J=8.8 Hz, 2H), 7.85 (s, 2H), 7.68 (dd, J = 5.9, 2.9 Hz, 2H), 7.59 (s, 2H), 3.29 (s, 2H), 1.95-1.74 (m, 8H), 1.57 (m,6H),1.33(m,6H).

[0043] The specific applications and effects of the present invention are as follows:

[0044] Use UV-visible spectrophotometer and fluorescence spectrophotometer to identify Cu 2+ And Zn 2+ The performance was studied. All tests are performed in acetonitrile solutio...

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Abstract

The invention relates to a probe for detecting copper ions and zinc ions. The probe is an imine derivative of [5] helicene. The imine derivative is complexed with copper ions, so that obvious absorption peaks appear in a visible light area, and the copper ions can be detected by using an ultraviolet-visible spectrum. The imine derivative is complexed with zinc ions, so that fluorescence is raised, and the zinc ions can be detected by using a fluorescence spectrum. A preparation method comprises the following steps: firstly, performing a reaction on a [5] helicene compound with hydroxyl and chloromethyl methyl ether; performing a reaction with butyl lithium and DMF continuously to introduce a formyl group on a ortho-position of hydroxyl; and performing a reaction with an amino compound continuously to generate the [5] helicene imine derivative DC. The probe provided by the invention has the advantages that the prepared helicene derivative DC is simple and convenient to synthesize, high in yield, easy to prepare and suitable for amplified synthesis and actual production and application; bivalent copper ions can be detected by using the ultraviolet-visible spectrum, and the bivalent zinc ions can be detected by means of the fluorescence method; the probe as a novel probe can be applied to the field of ion detection; the probe is good in molecular selectivity and high in sensitivity, has the advantages of fast response and obvious phenomenon, and has a wide application prospect.

Description

【Technical Field】 [0001] The invention belongs to the field of molecular probes for metal ion detection, in particular to a molecular probe for selective detection of copper ions and zinc ions, and a preparation method and application thereof. 【Background technique】 [0002] The ion probe can convert ion existence information into easily detectable light signals, and then obtain the recognition function of specific ions. The interaction with specific ions in the system will have specific physical and chemical changes, which will cause the corresponding optical signal to change. The ion probe has many advantages such as high sensitivity, simplicity and ease of use. [0003] Copper ion is one of the common toxic heavy metals, which has serious harm to animals, plants and the environment. At the same time, copper ions are also essential trace elements for the human body, which are related to cell reproduction, endocrine and hematopoietic functions. However, if excessive copper ions ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C249/02C07C251/24C09K11/06G01N21/64G01N21/33
CPCC07C251/24C09K11/06C09K2211/1007C09K2211/1011G01N21/33G01N21/64
Inventor 胡志强王鲲鹏雷洋陈绍晋陈聚朋郑文君
Owner 东营睿港投资服务有限责任公司
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