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A fluorescent probe and molecular technology, which is applied in the direction of fluorescence/phosphorescence, luminescent materials, and material analysis through optical means, which can solve the problems of poor ion detection
Inactive Publication Date: 2014-01-22
JIANGNAN UNIV
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The currently studied rhodamine and its derivatives generally have good detection ability for a metal ion, but poor detection for other ions, that is, a rhodamine d...
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Embodiment 1
[0017] Embodiment 1, the synthesis of rhodamine lactam (SRhB)
[0018] 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
[0019] Embodiment 2, the preparation of adamantane-rhodamine (SRhB-AD)
[0020] Add 100mg maleic anhydride (MAH), 516mg SRhB, 20mgDMAP, 5mL DMSO to a 50mL single-necked flask, react at room temperature for 12h, add 191mg EDC, 137mg HOBt, activate for 1h, add 151.25mg amantadine (AD) and react at room temperature for 12h. 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
[0021] Embodiment 3, detect iron ion
[0022] Configure 1.4×10 in a 100mL volumetric flask -3 SRhB-AD standard solution of M, 7×10 -3 M iron ion standard solution; pipette 2.5mL1.4×10 in a 20mL volumetric flask -3 M SRhB-AD standard solution and 0.2, 0.5, 0.7, 1, 1.5, 2, 2.5mL iron ion standard solution, ultrapure water to constant volume, measure fluorescence intensity at 587nm, and perform photometry at 563nm.
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Abstract
The invention provides a novel rhodamine fluorescence probe, and belongs to the field of function materials. The novel rhodamine fluorescence probe provided by the invention is characterized in that rhodamine B (RhB) is used as a raw material and is modified by using diamine so as to prepare rhodamine lactam, further the rhodamine lactam reacts with maleic anhydride (MAH) and amantadine so as to obtain the rhodamine fluorescence probe, and the novel rhodamine fluorescence probe contains multiple amido functional groups and carbon-carbon double bonds, wherein the multiple amido functional groups can react with metal ions, and the carbon-carbon double bonds can react with Hg<2+>. After the spiral rhodamine lactam compound is combined with heavy metal particles, the protonation of lactam nitrogen atoms can result in the reduction of the charge density of the nitrogen atoms, thus the cracking of a C-N chemical bond at the spiral center is triggered, so as to generate the fluorescence change and the color change. The obtained rhodamine derivative has relatively good recognition capability on mercury ions and iron ions in a water solution, the detection limit of the obtained rhodamine derivative on the iron ions reaches 8.3ppm, and the detection limit of the obtained rhodamine derivative on the mercury ions reaches 4.7ppm. The prepared rhodamine derivative can serve as the fluorescence probe and is widely applied to the fields such as environmental engineering, detection and the like.
Description
technical field [0001] The invention relates to the design and preparation of rhodamine fluorescent probe molecules and belongs to the field of functional materials. Background technique [0002] With the development of industry, more and more heavy metal ions are lost to the natural environment, which brings serious environmental hazards. For example, mercury ions are easily oxidized to methylmercury in aqueous solution, which has the potential to affect humans and natural ecosystems through the food chain. Long-term exposure to high concentrations of mercury ions will cause serious damage to the central nervous system and other organs such as the heart, kidneys, lungs, etc.; at the same time, due to the bactericidal effect of silver in recent years, the use of silver is increasing. For example, silver is incorporated into detergents and wound dressings, etc. After use, these silver nanoparticles and ions end up in rivers and so on. Although the original methods for the de...
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