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Fluorescent probe benzothiazole-terpyridine compound for distinguishing and detecting zinc ions and cadmium ions and its preparation and application method

A technology of benzothiazole and terpyridine, which is applied in the chemical field, can solve the problems that limit the practical application of fluorescent probes and cannot effectively distinguish between zinc ions and cadmium ions, and achieve the effect of simple preparation process and wide application prospects

Active Publication Date: 2015-09-02
浙江富昇科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since zinc and cadmium belong to the same group of elements, they have extremely similar extranuclear electron configurations and the same coordination number, so those that coordinate with zinc ions can also coordinate with cadmium ions, so the existing fluorescent probes often The inability to effectively distinguish between zinc ions and cadmium ions limits the practical application of these fluorescent probes, and there is a gap in the identification of zinc and cadmium ions by fluorescent probe methods

Method used

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  • Fluorescent probe benzothiazole-terpyridine compound for distinguishing and detecting zinc ions and cadmium ions and its preparation and application method
  • Fluorescent probe benzothiazole-terpyridine compound for distinguishing and detecting zinc ions and cadmium ions and its preparation and application method
  • Fluorescent probe benzothiazole-terpyridine compound for distinguishing and detecting zinc ions and cadmium ions and its preparation and application method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Synthesis of fluorescent probe 4-(4-benzothiazolylphenyl)ethynyl terpyridine.

[0036] (1) Synthesis of 2-(4-bromophenyl)benzothiazole

[0037]Add 0.46g (2.5mmol) p-bromobenzaldehyde and 0.31g (2.5mmol) o-aminothiophenol into 25mL triethyl phosphate, stir for 10min, add 2.5mL glacial acetic acid, stir rapidly and heat up to 60°C, add 1.8g (3.75mmol) lead tetraacetate, stirred for 30 minutes, cooled to room temperature, added 100mL water and 50mL dichloromethane, separated, collected the organic phase, extracted the aqueous layer with dichloromethane three times (50mL×3), collected and combined The organic phase was dried with anhydrous magnesium sulfate, the solvent was evaporated to dryness, and the obtained solid was separated and purified by 100-200 mesh silica gel column chromatography (dichloromethane: petroleum ether = 1:2) to obtain the product 2-(4-bromobenzene Base) benzothiazole 0.46g, yield 63%. Its melting point was measured to be 137.2°C.

[0...

Embodiment 2

[0048] Example 2: The response of the fluorescence spectrum of the fluorescent probe 4-(4-benzothiazolylphenyl)ethynyl terpyridine (compound I) to zinc ions and cadmium ions.

[0049] Prepare an aqueous solution with a zinc ion and cadmium ion concentration of 25-450nM, take 5mL of zinc ion and cadmium ion aqueous solutions of different concentrations and 5mL of aqueous solutions without zinc ion and cadmium ion, and add 1×10 -4 M compound I in acetonitrile solution 50 μL, after shaking evenly, test its fluorescence spectrum. The test conditions are: excitation wavelength 375nm, slit width 2.5nm / 2.5nm, voltage 700V. Test results such as figure 1 (containing zinc ions) and figure 2 (Contains cadmium ions).

[0050] From figure 1 It can be clearly found that in the aqueous solution without zinc ions, the fluorescence emission peaks of compound I are split peaks, which are respectively located at 380nm and 400nm. When the concentration of zinc ions in the solution is lower ...

Embodiment 3

[0053] Example 3: The fluorescence spectrum of the fluorescent probe 4-(4-benzothiazolylphenyl)ethynyl terpyridine (compound I) responds to zinc ions and cadmium ions in the presence of interfering ions.

[0054] Ni with a concentration of 0.25 μM was respectively configured 2+ , Ca 2+ , Mg 2+ 、Al 3+ , Zn 2+ 、K + , Pb 2+ 、Co 2+ 、Cd 2+ 、Cr 2+ 、Cu 2+ and Na + Ionic aqueous solution, and each 5mL was added to it with a concentration of 2.5×10 -5 M compound I in acetonitrile solution 50 μL, after shaking evenly, test its fluorescence spectrum. The test conditions are: excitation wavelength 375nm, slit width 2.5nm / 2.5nm, voltage 700V. Test results such as image 3 and Figure 4 shown.

[0055] From image 3 It can be seen that when the solution does not contain zinc ions, the fluorescence intensity of the probe does not change significantly before and after adding various common metal cations in the aqueous solution. When the concentration of zinc ions in the solut...

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Abstract

The invention discloses a fluorescent probe: a benzothiazole-terpyridine compound used for distinguishing and detecting zinc ions and cadmium ions. The probe has a structural formula as shown in (I). The compound is prepared by using bromobenzaldehyde and O-aminothiophenol as raw materials, and performing a dehydration cyclization reaction, a coupling reaction and a terpyridine derivative reaction. According to the invention, the raw materials are cheap and easily available, a synthesis route is simple, a yield is relatively high, and the fluorescent probe is high in fluorescence quantum efficiency, and relatively high in heat stability and dissolvability. The probe uses a photoinduced charge transfer mechanism, has different luminescence response for the zinc ions and the cadmium ions, has characteristics of rapid response, high sensitivity and high selectivity, is suitable for food safety inspection, laboratory safety inspection, and especially industrial wastewater monitoring, and has a wide application prospect in environment monitoring, ecological protection, disease diagnosis, industrial production and sewage inspection.

Description

technical field [0001] The invention relates to the fields of chemistry and fluorescent probes. Background technique [0002] Zinc ions and cadmium ions are metal elements of the same group, but they play completely different roles in biological and physiological processes. Zinc ions are the second most abundant metal ion in the human body and are involved in many physiological activities, including gene transcription, protease catalysis, metalloenzyme regulation, nerve signal transmission, and cell metabolism. Too low a zinc ion concentration can lead to a series of pathological events. In contrast, intake of cadmium ions by the human body can lead to acute or chronic poisoning symptoms, and cadmium ions can also accumulate in the human body, causing cancer and other complications. In recent years, medical research has found that long-term exposure to cadmium ions can also lead to gene mutations. However, as an important alloy component, cadmium has been widely used in e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14C09K11/06G01N21/64
Inventor 钱国栋谭轶群杨雨崔元靖郁建灿王智宇樊先平王民权
Owner 浙江富昇科技有限公司
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