Biological silver ion fluorescent probe containing triazole anthraquinone derivative and preparation method and application thereof
An anthraquinone derivative, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effect of good commercial application value, high sensitivity, good water solubility
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Embodiment 1
[0037]
[0038] Synthesis of 1,8-Dipropargyl Anthraquinone Intermediate 1
[0039]The basic compounds sodium carbonate (42 mmol) and 3-bromo-1-propyne (2.6 mL, 33.5 mmol) were added to a 250 mL circle containing 1,8-dihydroxyanthraquinone (2.013 g, 8.38 mmol dissolved in 100 mL DMF) Stir the reaction in a bottom flask at room temperature. The color of the reaction solution changes from yellow to brown. TLC detects that the raw material is completely reacted, washed with water, extracted with carbon dichloride to obtain an organic phase, and then separated by column chromatography to obtain a yellow solid 1,8-diyne Propylanthraquinone intermediate 1 (2.330 g, 88% yield).
[0040] 1 H NMR (600MHz, DMSO) δ 7.77 (dt, J = 20.4, 7.2Hz, 1H), 7.60 (d, J = 7.8Hz, 1H), 5.02 (s, 1H), 3.66 (s, 1H).
[0041] Synthesis of Azidopropanol or Azidohexanol
[0042] Add sodium azide (4.34g, 66.9mmol) into a 50mL round-bottomed flask containing bromopropanol (2mL, 22.3mmol dissolved in 100mL...
Embodiment 2
[0048] Fluorescence Spectrometry Conditions
[0049] The excitation slit width is 10.0nm, the emission slit width is 20.0nm, the excitation wavelength is 340nm, the response time is 1s, and the sensitivity is high. The sample cell is a double-pass quartz cuvette and a four-pass quartz cuvette with a 1cm optical path.
[0050] Using dimethyl sulfoxide as the solvent, accurately prepare the molar concentration in a 5mL volumetric flask to be 1.0×10 -2 mol / L fluorescent probe K-1, K-2 solution and constant volume, take 25 μL mother solution in 5mL colorimetric tube and constant volume, at this time the molar concentration of fluorescent probe is 50 μM; then use HEPES buffer to prepare molar The concentration is 1.0×10 -3 mol / L of various metal salt solutions were also diluted to a molar concentration of 50 μM with HEPES buffer.
[0051] The testing conditions of fluorescent probes K-1 and K-2 are Ex=10.0nm and Em=20.0nm.
Embodiment 3
[0053] Selective recognition of different metal ions by fluorescent probe K-1
[0054] Prepare a fluorescent probe solution with a molar concentration of 0.05mmol / L with a buffer solution with a volume ratio of HEPES:DMSO=7:1, and then add 20 equivalents of Ag to the fluorescent probe solution + 、Al 3+ 、Ba 2+ , Ca 2+ 、Cd 2+ 、Co 2+ 、Cr 3+ 、Cu 2+ , Hg 2+ , Fe 3+ 、K + , Mn 2+ 、Na + , NH 4 + 、Ni + , Pb 2+ and Zn 2+ Plasma and blank fluorescent probe solution. The results show that the system containing the blank fluorescent probe solution and other metal ions has almost no fluorescence emission at the maximum absorption wavelength of 466nm. After adding 20 equivalents of silver ions to the blank fluorescent probe solution, the fluorescence of the system at 466nm increased rapidly, as figure 1 shown. The experimental data show that the fluorescent probe K-1 has a positive effect on Ag + Has a high selective recognition ability.
[0055] Detection of Ag by Coexi...
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