Near infrared waveband reaction type biological thiol two-photon fluorescent probe as well as preparation method and application thereof
A fluorescent probe and near-infrared technology, applied in the field of fluorescent probes, can solve problems such as limiting the scope of application, and achieve the effects of high sensitivity, good biocompatibility and strong selectivity
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Embodiment 1
[0019] (1) The preparation method of fluorescent probe molecule BODIPY-DS is:
[0020] Under the protection of an inert gas and at 0°C, fluoroboron dipyrrole conjugated arylphenol BODIPY-OH (0.59g, 1.00mmol) was dissolved in 10mL of dry dichloromethane, and 2,4-dinitrobenzenesulfonyl chloride ( 0.58g, 2.18mmol), then add 10mL of dry dichloromethane and triethylamine (2.18mmol), stir and react for 10h, after the reaction, extract, dry, concentrate, and purify by column chromatography to obtain the fluorescent probe molecule BODIPY -DS, yield 45%.
[0021] The synthetic route of compound BODIPY-DS is as follows:
[0022]
[0023] Among them, fluoroboron dipyrrole conjugated arylphenol BODIPY-OH was prepared according to the literature method (Bao-xingShen, YingQian. A novel triphenylamine-BODIPY dendron: click synthesis, near-infraredemission and a multi-channelchemosimeter for Hg 2+ and Fe 3+ . Journal of Materials Chemistry B, 2016, 4, 7549-7559).
[0024] (2) Structura...
Embodiment 2
[0030] The preparation method of fluorescent probe molecule BODIPY-DS is basically the same as in Example 1, the difference is:
[0031] Under the protection of an inert gas and at 0°C, fluoroboron dipyrrole conjugated arylphenol BODIPY-OH (0.59g, 1.00mmol) was dissolved in 10mL of dry dichloromethane, and 2,4-dinitrobenzenesulfonyl chloride ( 0.64g, 2.40mmol), then add 10mL of dry dichloromethane and triethylamine (2.40mmol), and stir the reaction for 12h. After the reaction, the fluorescent probe molecule BODIPY-DS was obtained through extraction, drying, concentration and column chromatography purification, with a yield of 48%.
Embodiment 3
[0033] The preparation method embodiment 1 of fluorescent probe molecule BODIPY-DS is basically the same, the difference is:
[0034] Under the protection of an inert gas and at 0°C, fluoroboron dipyrrole conjugated arylphenol BODIPY-OH (0.59g, 1.00mmol) was dissolved in 10mL of dry dichloromethane, and 2,4-dinitrobenzenesulfonyl chloride ( 0.66g, 2.48mmol), then added 10mL of dry dichloromethane and triethylamine (2.48mmol), and stirred for 12h. After the reaction is completed, the fluorescent probe molecule BODIPY-DS is obtained through extraction, drying, concentration and column chromatography purification, with a yield of 50%.
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