A fluorescent probe compound containing coumarin-thiadiazolyl Schiff base and its preparation method and application
A thiadiazole-based, fluorescent probe technology, used in chemical instruments and methods, organic chemistry, fluorescence/phosphorescence, etc., can solve the problems of expensive instruments and high analysis costs, achieve strong anti-interference ability, and realize naked-eye recognition and comparison. The effect of color analysis
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Embodiment 1
[0034] Embodiment 1: the synthesis of fluorescent probe compound (L) of the present invention
[0035] Weigh 0.245g (1.0mmol) 3-formyl-7-N, N-diethylaminocoumarin and 0.147g (1.1mmol) 5-amino-1,3,4-thiadiazole-2- Mercaptans were dissolved in 10mL of absolute ethanol, stirred to fully dissolve; the mixture was added to a round bottom flask, and a drop of glacial acetic acid was added as a catalyst, and the temperature was raised to 75°C and refluxed for 6h. After the reaction solution was cooled, it was suction filtered and Recrystallized from absolute ethanol, filtered with suction, washed and dried to obtain 0.297 g of the product with a yield of 82.4%.
[0036] FT-IR (KBr, cm -1 ): 3431 (S-H stretching vibration), 2976, 2929 (-CH 2 and -CH 3 stretching vibration), 1738 (C=O stretching vibration), 1615, 1502 (benzene ring stretching vibration), 1348 (-C-H bending vibration), 1132 (-C-N stretching vibration), 683 (-N-H out-of-plane bending vibration).
[0037] 1 H NMR (40...
Embodiment 2
[0038] Embodiment 2: the ultraviolet-visible absorption spectrometry of fluorescent probe compound L
[0039] Accurately weigh 3.6 mg of fluorescent probe compound L, dissolve and prepare a concentration of 1.0×10 -2 mol / L acetonitrile stock solution; dilute the stock solution to a concentration of 1.0×10 with a mixture of acetonitrile and water at a volume ratio of 1:1 -5 mol / L of the solution to be tested. Take 3mL concentration as 1.0×10 -5 mol / L of the solution to be tested in a quartz cuvette (the thickness of the quartz cuvette is 1cm), and then add 3 μL of the solution at a concentration of 1.0×10 -2 mol / L of various metal ions (Na + , K + , Ag + , Ca 2+ , Mg 2+ , Mn 2+ , Cd 2+ , Cr 3+ , Cu 2+ , Ni 2+ ,Co 2+ , Fe 3+ , Fe 2+ , Hg 2+ ) aqueous solution, shake well, and measure the UV-Vis absorption spectrum of the solution after 1 minute (see figure 1 ). Before adding metal ions, the ultraviolet-visible absorption spectrum of the fluorescent probe compou...
Embodiment 3
[0040] Embodiment 3: the determination of the ultraviolet-visible absorption spectrum titration experiment and detection limit of fluorescent probe compound L
[0041] Take 3mL concentration as 1.0×10 -5 mol / L of the solution to be tested in the quartz cuvette, add 3, 6, 9, 12, 15, 18, 21, 24, 27, 30μL respectively to a concentration of 1.0×10 -3 mol / L Cu 2+ Ionic water solution, shake well, and measure the UV-Vis absorption spectrum of the solution after equilibration (such as figure 2 shown). With Cu 2+ With the addition of ions, the absorbance of the fluorescent probe compound L at 446nm gradually increases, while the absorbance at 506nm gradually weakens, and an obvious equivalence point appears at 469nm, which indicates that the volume ratio of acetonitrile and water is 1:1. The fluorescent probe compound L in the mixed solution can interact with Cu 2+ ions form stable complexes, Cu 2+ ions at 1.0 x 10 -6 ~1.2×10 -5 In the range of mol / L, Cu 2+ There is a good l...
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