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Synthesis And Properties Of Dicyanomethylene-benzopyran And Aza-coumarin-based Near-infrared Fluorescent Probes

Posted on:2018-09-22Degree:MasterType:Thesis
Country:ChinaCandidate:M X LiFull Text:PDF
GTID:2321330518975731Subject:Organic Chemistry
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Fluorescent probes have been widely used in biological, environmental, chemical and other fields in recent years because of their low cost,high selectivity, high sensitivity,biological compatibility and real-time detection. Compared with fluorescent probes in visible light, near-infrared (NIR, 650-900 nm) fluorescent probes not only have deeper tissue penetration ability, but also cause less damage to biological samples and produce negligible background interference fluorescence, so it is highly favorable for bioimaging applications. Therefore, the development of near-infrared fluorescent probe is of great significance. In this thesis, we developed two NIR fluorescent probes and studied their optical properties and practical applications.1. A dicyanomethylene-benzopyran (DCMB)-based NIR fluorescent probe was synthesized and its structure was confirmed by 1H NMR, 13C NMR, MS and HR-MS.This probe uses 2, 4- dinitrobenzene ether as the reaction site. Experiments showed that this probe can be used to rapidly and selectively detect selenocysteine (Sec) under mild conditions, accompanied by distinct color changes and significant NIR fluorescent signal enhancement. In addition, this probe can be used to detect and image both exogenous and endogenous Sec in living cells, indicating that this probe has great potential for applications in the field of biology.2. We designed and synthesized a colorimetric and ratiometric aza-coumarin-based NIR fluorescent probe for detection of bisulfite/sulfite and its structural was confirmed by 1H NMR, 13C NMR, MS and HR-MS. Experiments showed that this probe can be used to rapidly (<30 s) and selectively detect bisulfite under mild conditions, showing distinct color changes and significant ratiometric fluorescence changes. Moreover, this probe can be conveniently used to detect bisulfite in food samples and image both exogenous and endogenously generated bisulfite in living cells. It is indicated that this probe has good application prospect.
Keywords/Search Tags:fluorescent probe, near-infrared, dicyanomethylene-benzopyran, selenocysteine, aza-coumarin, bisulfite
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