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Synthesis And Properties Of Organic Two-photon Functional Materials Based On Triphenylamine And Spirobifluorene Structure

Posted on:2018-04-29Degree:MasterType:Thesis
Country:ChinaCandidate:S Z LiFull Text:PDF
GTID:2351330515481708Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
With the continuous development of science and technology,people have more knowledge of the nature mystery.We are eager to recognize the life system,to explore the life and chemistry of the unknown world.Fluorescent probe is a kind of high sensitivity,good selectivity,easy detection,low detection limit technology of micro-analysis,in recent years it has become a hot research field.Organic two-photon fluorescent probe can carry out deep-level high-resolution and non-destructive imaging of the cells,enable dark field imaging and avoid fluorescence bleaching.Two-photon transition has a strong selectivity,so it is beneficial to image some special substances in biological tissue.Spirofluorene compounds have the advantages of high fluorescence quantum yield,high molar absorptivity,easy structure modification and m?ltiple reactive sites.On the other hand,the three-dimensional structure can effectively avoid the close accum?lation of chromophores in the compounds,Which is beneficial to improve the solubility and thermal stability of the material.Therefore,the subject was designed with spiramine as the mother.The triphenylamine group is connected to the fluorene ring to form a two-photon absorption unit,and then the amine group is derivatized to expect obtain an organic two-photon functional material with excellent performance.This article will introduce the workmainly from the following sections :The first part:a kind of "up-and-down" asymmetric t-butyl spiramine was synthesized from cheap biphenyl as raw material,and five compounds were synthesized by derivatization of amino groups.SPF-B,SPF-SPA,SPF-MLG,SPF-CN,SPF-CP were synthesized and characterized.The second part: the performance of the compound SPF-SPA was studied.It was found that it was a highly sensitive "turn-on" type fluorescent probe,which co?ld detect Hg2 + and Cl O-.The detection limits are 3.05×10-8M and 2.30×10-8M,and it can be used in cell imaging.It is also a strong acid pH probe,calc?lated that pKa = 2.11.The two-photon absorption properties of SPF-SPA was studied,and its two-photon absorption cross section is 663 GM and active absorption cross section is 485 GM.Its two-photon absorption cross section and reactive cross section are higher,show that it has good two-photon absorption performance.The third part:(1)The properties of the compounds SPF-B and SPF-MLG were studied respectively.After testing the water content in the organic solvent,the conclusion was that the SPF-B had a limit of 0.0056% for the water in tetrahydrofuran,and SPF-MLG in the DMSO of the water detection limit is 0.01533%.They are two high sensitivity fluorescent probe of the water content in the organic solvent.At the same time,the SPF-MLG can be used as a good alkaline fluorescent probe.(2)The spectral properties of the compound SPF-CN were tested.It was found that it was a naked eye colorimetric fluorescence sensor for detecting protons in organic solvents.It provided a new method for the detection of proton content in organic solvents.(3)The performance of the compound SPF-CP was studied.It was found that SPF-CP co?ld change color only in CH2Cl2 with the irradiation of ?ltraviolet light in various organic solvents,and it co?ld be used as the naked eye colorimetric probe to detect CH2Cl2.
Keywords/Search Tags:spirofluorene, fluorescence probe, triphenylamine, two photons, water content, pH
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