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Design And Synthesize Novel Rhodamine Fluorescence Probe Study And Identification Of Fe 3 + Of

Posted on:2015-03-31Degree:MasterType:Thesis
Country:ChinaCandidate:W F MengFull Text:PDF
GTID:2261330428477202Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Iron as the second content of metal elements in the crust, but also the tallest in the body content of trace elements, participate in the physiological activities of the organisms, such as muscle contraction, nerve conduction, enzyme catalysis, the synthesis of DNA and RNA, osmotic regulation in cells, and acid-base balance to maintain plays a very important role. Therefore, detected the Fe3+inside and outside of the organisms has been an important research topic. Compared with the traditional detection methods, fluorescence analysis due to its high detection sensitivity, simple operation, good reproducibility, no loss, made it widely used and developed rapidly. In this paper, made full use of lactam structure of rhodamine, a series of fluorescent sensors were designed to detect Fe3+. The details are summarized as follows:Firstly, different substituents amino compounds intermediates were synthesized from amino thiourea, amino benzenethiol as the starting material and then to use the acetonitrile as solvent, through intermolecular condensation with rhodamine derivatives to give fluorescence probes L1-L8, and the compounds structure were confirmed by1H NMR,13CNMR, X-Ray, IR and HRMS-ESI. We through experiments also study of reactant molar rations between the impact on the product yield.Secondly, the spectroscopic properties of molecular fluorescent probes L1-L8were studied in the methanol-water (1:1, v/v). Fluorescence probes L1-L8were colorless and scarcely showed fluorescence emission in the absence of Fe3+, with lactam structure as the predominant species. Upon binding with Fe3+, the intense emission peak intensity increased dramatically, coupled with a clear color change from colorless to pink. The titration curve showed a smooth and steady increase, and about1.0equiv of Fe3+was required until a plateau was reached. A Job’s plot experiment indicated that L1-L8chelated Fe3+with1:1stoichiometry. This observation suggested that probes L1-L8emission intensity almost unaffected in the pH range of4-7, and these will be very important for the applications in both environment and living cells.Thirdly, As a logical extension, fluorescence probes L2-L5under the focus of laser scanning microscopy to identify Fe3+in the human liver cancer cells (HepG2) biological cells in imaging experiments showed that probe compounds not only have great choice efficient identification ability to Fe3+in the microenvironment, and close integration with the target molecules, hardly affect the molecular structure and biological activity of the object, have very excellent anti-interference ability. Moreover, fluorescence imaging for Fe3+in living cells showed fluorescence probes L2-L5have ideal spectroscopic properties that satisfy the criteria for further biological applications and have important guiding significance.
Keywords/Search Tags:rhodamine, molecular fluorescent probe, recognition, metal ions, cells imaging
PDF Full Text Request
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