Rhodamine fluorescent probe capable of detecting and separating heavy metal ions, and preparation method of rhodamine fluorescent probe
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A technology of heavy metal ions and fluorescent probes, used in fluorescence/phosphorescence, alkali metal compounds, chemical instruments and methods, etc.
Active Publication Date: 2014-11-12
JIANGNAN UNIV
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Although a lot of research work has reported the detection of heavy metal ions, there is no
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Embodiment 1
[0023] Embodiment 1, the synthesis of rhodamine lactam (SRhB)
[0024] RhB (10.46mmol) was dissolved in 180ml absolute ethanol, N 2 Quickly add 40.23mL of ethylenediamine under the atmosphere, slowly add the temperature to 85°C, react for 24h, and distill under reduced pressure, the obtained powder is distilled with CH 2 Cl 2 (100mL) was dissolved, extracted with water (200mL), the organic layer was separated, washed with water 5 times, and distilled under reduced pressure to obtain an orange powder. Chromatography on silica gel (CH 2 Cl 2 / EtOH / Et 3 N=5:1:0.1) purification, yield 90%.
Embodiment 2
[0025] Embodiment 2, the preparation of azobenzene-rhodamine (SRhB-Azo)
[0026]Add 100mg maleic anhydride (MAH), 516mg SRhB, 20mg DMAP, 5mL DMSO to a 50mL one-necked flask, react at room temperature for 12 hours, add 191mg EDC, 137mg HOBt, activate for 1 hour, add 197.24mg azobenzene (Azo) and react at room temperature for 12 hours . The resulting powder was washed with CH 2 Cl 2 (100mL) was dissolved, extracted with water (200mL), separated the organic layer, and distilled under reduced pressure to obtain a pink powder, which was purified by silica gel chromatography (CH 2 Cl 2 ).
Embodiment 3
[0027] Embodiment 3, detect mercury ion
[0028] Configure 2.5×10 in a 100mL volumetric flask -3 M's SRhB-MAH-A 2 O ethanol standard solution, 1×10 -4 M mercury ion standard solution. Take 1mL of SRhB-Azo standard solution and 0.1mL, 0.2mL, 0.4mL, 0.6mL, 0.8mL, 1.0mL of mercury ion standard solution in a centrifuge tube, dilute to 5mL with ethanol, measure the fluorescence intensity at 492nm, and carry out at 563nm Photometry.
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Abstract
The invention provides a rhodamine fluorescent probe capable of detecting and separating heavy metal ions, and a preparation method of the rhodamine fluorescent probe, belonging to the field of a functional material. The fluorescent probe is prepared by comprising the following steps: modifying rhodamine B (RhB) serving as raw material so that the terminal has an azobenzene group; preparing the rhodamine fluorescent probe capable of detecting metal mercury ions and having a relatively low detection limit. By utilizing subjective-objective clathration action of azobenzene and cyclodextrin and taking the cyclodextrin magnetic nanoparticles prepared in advance as an adsorbent, the clathrated fluorescent probe and the detected metal ions can be separated from a solution under the action of an external magnetic field; furthermore, by utilizing the photoreaction property of the azobenzene group, the removal of heavy metal ions and the repeated use of the cyclodextrin magnetic nanoparticles can be realized. The rhodamine derivative has relatively good identification capability to mercury ions in the aqueous solution, thus being used as a mercury ion detection and removal agent. As the fluorescent probe, the rhodamine derivative can be widely applied to the fields of environmental engineering, analysis and detection and the like.
Description
technical field [0001] The invention relates to the design, preparation and application of rhodamine fluorescent probe molecules, and belongs to the field of functional materials. Background technique [0002] A series of highly toxic heavy metals such as copper (Cu), mercury (Hg), and lead (Pb) have been widely used in various industrial production processes, and most of them are finally converted into cations and discharged into nature, so that heavy metals are harmful to water. And air pollution is becoming more and more serious and frequent. However, some heavy metal ions are highly toxic or have a very important impact on life processes. For example, mercury ions are easily oxidized to methylmercury in aqueous solution, which is potentially harmful to humans and natural ecosystems through the food chain. Long-term exposure to high concentrations of mercury ions can damage the central nervous system and other organs such as the heart, kidneys, lungs, etc. Therefore, it...
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