Cadmium-ion fluorescence probe based on pyrene exciplex, and preparation method and application thereof

A technology of fluorescent probes and cadmium ions, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials. simple route effect

Active Publication Date: 2017-06-20
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These cadmium ion probes usually have good sensitivity and fast response time, but their binding selectivity to cadmium i

Method used

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  • Cadmium-ion fluorescence probe based on pyrene exciplex, and preparation method and application thereof
  • Cadmium-ion fluorescence probe based on pyrene exciplex, and preparation method and application thereof
  • Cadmium-ion fluorescence probe based on pyrene exciplex, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0026] Example 1: Exciplex-type cadmium ion fluorescent probe, the basic synthesis process is as follows:

[0027] 1) Synthesis of 1-(2-chloroacetyl)pyrene: add 1g of 1-aminopyrene to a one-necked bottle, add 100mL of CH 2 Cl 2 As a solvent, 0.9 g of DMAP was added, and 0.43 mL of chloroacetyl chloride was slowly added dropwise thereto under ice-cooling conditions. Slowly rose to room temperature and stirred for 6h. After the reaction was completed, the solvent was evaporated by rotary evaporation, and passed through a silica gel column, eluting with petroleum ether:ethyl acetate=10:1. The eluent containing the product was collected by spin-drying, and the product was a white solid with a yield of 74%. The H NMR spectrum and carbon spectrum of the intermediate are as follows: image 3 , Figure 4 shown.

[0028] 2) Synthesis of the probe: Add 0.63g of 1-(2-chloroacetyl)pyrene to a one-necked bottle, add 150mL of acetonitrile as a solvent, then add 0.38g of KI and 6mL of ...

Example Embodiment

[0030] Embodiment 2: The fluorescent probe prepared in embodiment 1 is to the response situation of cadmium ion determination

[0031] The probe prepared in Example 1 was dissolved in CH 3 CN solution, added to CH 3 CN:H 2 In O(1:19, v / v) mixed solvent, the concentration of the probe was prepared to be 10 -5 M solution, test its fluorescence spectrum changes.

[0032] Figure 7 When the concentration of the probe is 10 μM, when the concentration of cadmium ions is 5 μM, the fluorescence spectrum is significantly enhanced at 490 nm, indicating that after the two molecular probes are combined with a cadmium ion in a 2:1 manner, the two pyrene fluorophores are close to each other. Exciplex fluorescence peaks are produced. Its excitation wavelength is 360nm.

Example Embodiment

[0033] Embodiment 3: the fluorescent probe prepared in embodiment 1 and cadmium ion in CH 3 Complexation ratio in CN solution

[0034] The CH that the probe prepared in Example 1 is dissolved in 3 In the CN solution, the probe concentration was prepared to be 10 -5 The solution of M, the change of the fluorescence spectrum after the test probe is complexed with different metal ions. The added metal ions are 3eq of the probe concentration, which are Zn-containing 2+ , Fe 3+ , Cr 3+ , Ni2+ ,Co 2+ , Pd 2+ , Ag + , Cu 2+ , Hg 2+ , Mn 2+ , Cu + , Fe 2+ , Cd 2+ , Na + , Pb 2+ , Ca 2+ , Pt 2+ , Mg 2+ , K + Aqueous perchlorate solution. The result is as Figure 8 , indicating that the addition of excess Cd 2+ , will make the probe with Cd 2+ A 1:1 complexation is formed, resulting in a certain degree of quenching of the monomer fluorescence peak.

[0035] Keep the sum of the concentration of probe and cadmium ion at 10 μM in CH 3 CN: H2O=5:95(v / v) Solvent resp...

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Abstract

The invention provides a cadmium-ion fluorescence probe based on a pyrene exciplex, and a preparation method and application thereof. The probe has a structure as described in the specification. The preparation method comprises the following steps: dissolving 1-aminopyrene in CH2Cl2, then adding DMAP and slowly adding chloroacetyl chloride drop by drop under an ice-bath condition; allowing the temperature of a mixture obtained in the previous step to slowly rise to room temperature, removing the solvent through rotary evaporation after completion of a reaction, and loading a reaction product into a silica gel column; adding acetonitrile into obtained 1-(2-chloroacetyl)pyrene, then adding KI and DIPEA and slowly adding DPA drop by drop; and carrying out a reflux reaction, carrying out spin-drying to remove the solvent after completion of the reaction and treating a product of the reflux reaction with the silica gel column. The probe provided by the invention can emit fluorescent response signals specific to cadmium ions and is applicable to detection of cadmium ions in environment.

Description

technical field [0001] The invention belongs to the field of chemical analysis and detection, and in particular relates to a cadmium ion fluorescent probe based on a pyrene exciplex, a preparation method and an application thereof. Background technique [0002] Cadmium is one of the most threatening and toxic metals to humans and the environment. In nature, cadmium ions are absorbed by various animals and plants and enter the human body through food chain enrichment, causing a series of harmful effects on human health. Although cadmium ions have adverse effects on the environment and human health, it is still widely used in industrial production processes. Therefore, it is very necessary to find a fast and efficient detection method for cadmium ion, so that it can be applied in medicine, environment, food and other fields. Fluorescence detection method is simple and has outstanding advantages in sensitivity, selectivity, response time and biological application. In recent...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D213/38G01N21/64
Inventor 徐兆超刘洋赵秒
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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