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Coumarin structure-based specific thiophenol fluorescent probe and preparation method thereof
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A fluorescent probe, hydroxycoumarin technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of poor selectivity and slow reaction, and achieve easy separation, easy availability of raw materials, and novel structure. Effect
Inactive Publication Date: 2016-07-20
QILU UNIV OF TECH
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Most of the fluorescent probes reported so far have disadvantages such as poor selectivity and slow response, such as Kand, D.; Mandal, P.S.; Saha, T.; Talukdar, P.RSCAdv.2014, 4, 59579-59586. X.L.;Duan,X.Y.;Du,X.J.;Song,Q.H.Chem.Asian.J.2012,7,2696-2702, etc.
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Embodiment 1
[0016] Example 1: Dissolve 100.0mg (0.43mmol) 7-diethylamino-3-hydroxycoumarin in 3ml of anhydrousacetonitrile, add 0.12mL (0.86mmol) triethylamine, 114.4mg (0.43mmol) 2, 4-Dinitrofluorobenzene, nitrogen protection, room temperature reaction, TLC tracking reaction, complete reaction in 4 hours, extraction with ethyl acetate, drying the organic phase with anhydroussodiumsulfate, filtering, removing solvent under reduced pressure, separation and purification by silica gelcolumn chromatography 150.2 mg of reddish-brown solid was obtained, with a yield of 87.5%. 1 HNMR (400MHz, CDCl 3 ):δ8.88(s,1H),8.35(d,J=9.2Hz,1H),7.63(s,1H),7.32(d,J=8.8Hz,1H),7.15(d,J=9.2Hz ,1H),6.71(d,J=8.4Hz,1H),6.59(s,1H),3.45(q,J=7.2Hz,4H),1.24(t,J=7.2Hz,6H). 13 CNMR (100Hz, DMSO): δ156.59, 154.78, 154.32, 150.48, 141.49, 138.39, 133.35, 131.65, 129.52, 129.09, 121.57, 118.41, 109.67, 106.46, 96.74, 42.049.C 19 h 18 N 3 o 7 )m / z: calculated for [M+H] + :400.1145.Found[M+H] + :400.1147.
[0018] Example 3: Dissolve 100.0mg (0.43mmol) of 7-diethylamino-3-hydroxycoumarin in 3ml of anhydrous acetonitrile, add 0.12mL (0.86mmol) of Et 3 N, 114.4mg (0.43mmol) 2,4-dinitrofluorobenzene, nitrogen protection, reaction at room temperature, TLC tracking reaction, complete reaction in 4 hours, extraction with ethyl acetate, drying of the organic phase with anhydrous sodiumsulfate, filtration, subtraction The solvent was removed by pressure, separated and purified by silica gelcolumn chromatography to obtain 139 mg of reddish-brown solid with a yield of 80.1%.
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Abstract
The invention discloses a coumarin structure-based specific thiophenol fluorescent probe and a preparation method thereof. This probe is 7-diethylamino-3-(2,4-dinitrophenoxy)coumarin. In a DMF / HEPES buffer system, this probe selectively acts with thiophenol and releases strong fluorescent substance 7-diethylamino-3-hydroxycoumarin, enabling a reaction system to provide a strong fluorescent signal at wavelength of 48-3 nm. Experimental results show that this probe can specifically recognize thiophenol and is characterized by low detection limit (only 27 nM), large Stokes displacement and the like, and thiophenol can be qualitatively and quantitatively detected through fluorescence enhanced response of the probe upon thiophenol. This probe can be made by chemical synthesis, the synthetic process is simple and feasible, a detection method is simple to perform, high in sensitivity and good in selectivity, and therefore, this probe has practical application value in the environmental field.
Description
technical field [0001] The invention relates to the preparation of a thiophenol fluorescent probe based on a coumarin structure and the selective fluorescence detection of thiophenol, belonging to the field of organic small molecule fluorescent probes. Background technique [0002] Thiophenol is a highly toxic mercaptan pollutant, which is widely used in the production of chemical products. Its half-lethal concentration for fish is 0.01mM-0.4mM. Human exposure to thiophenol liquid or gas will cause serious damage to the central nervous system and other related systems, including shortness of breath, muscleweakness, nausea and vomiting, coma even death. And some aliphatic thiols play an important role in organic life. Therefore, it is of great significance to develop a method that can selectively distinguish thiophenols and aliphatic thiols. Fluorescent probe detection has the advantages of simple operation, high sensitivity, and high selectivity, and has received extensi...
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