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Fluorescent Probe For Hydrogen Sulfide Based On DCDHF

Posted on:2014-02-17Degree:MasterType:Thesis
Country:ChinaCandidate:T ChenFull Text:PDF
GTID:2231330398450855Subject:Fine chemicals
Abstract/Summary:PDF Full Text Request
Many kinds of messenger gas play an important role in organisms, fluorescence probes can be used to detect and sence biological signal gas such as H2S. NO, etc. Fluorescence probes have a wide range of applications in biological gas detection because of its high sensitivity, high response to the low concentration and its biocompatibility to cells.We should design fluorescence probes which can detect H2S accurately due to its significance as a biological signal gas. We ased on the mechanism of reduction reaction of azide by H2S to designe a new probe molecule for H2S detection, in this probe we used dicyanomethylenedihydrofuran (DCDHF)as fluorophore and azide group as H2S’s receptor.Because DCDHF is a molecule of D-π-A type and it has a P-πconjugate system, it’s excitation wavelength and emission wavelength are all in the long wavelength region. this is a kind of fluorescent molecular probes which has red light emission for hydrogen sulphide.We all know that within the scope of the red light wavelengths, the fluorescence probe can be avoided toxicity caused by uv light and also can be avaided the fluorescence interference by itself, and it has the asme optical window with the biological specimen, so that they can make best light penetration into various biological medium.With the addition of H2S to the solution of DCDHF-1, an emission centered at619nm was observed and increased in intensity significantly. Concomitantly, the solution color changes from yellow to red with the convenience and aesthetic appeal of a colorimetric assay. The probe has a high selectivity for H2S over competitive anions and sulfide-contining analytes. Finally, the probe was applied to sense H2S in living cells.4-amino or4-hydroxy-1,8-naphthalimide fluorophore with a pull-push electron system is characterized by the intramolecular charge transfer (ICT). When the electron-donating ability of4-amino or4-hydroxyl group in1,8-naphthalimide changes, a shift in the emission wavelength can be expected. In this thesis, a1,8-naphthalimide fluorescent probes based on the ICT mechanism were designed and synthesized. It is ased on the mechanism of reduction reaction of azide by H2S too.In the same way.we use4-amino-1,8-naphthalimide fluorophore as fluorophore, and double amino structure as a receptor to synthesized another fluorescent probe N-butyl-4-bromine-5-nitro-1,8-naphthalimide(3) for NO. According to a report in the literatures before that double amine under the condition of NO can be converted into triazole structure compound, and it will lose a proton under physiological conditions then form a triazole salt structure. We expect the probe3could detect NO with ratio fluorescence.
Keywords/Search Tags:DCDHF, Hydrogen sulfide, Red light emission, Naphthalimide
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