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New Rhodamine B Fluorescent Molecular Probe Synthesis And Study Of Metal Ion And Anion Recognition

Posted on:2011-06-03Degree:MasterType:Thesis
Country:ChinaCandidate:K LeiFull Text:PDF
GTID:2191360305493624Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Rhodamine compound is one type of the xanthene dye. The rhodamine framework is an ideal mode to construct OFF-ON fluorescent chemosensors due to its particular structural property. Rhodamine derivatives with spirolactam structure are nonfluorescent, whereas ring-opening form of the spirolactam gives rise to a strong fluorescence emission. Moreover, the rhodamine fluorophore has a longer emission wavelength (over 550 nm), which is often preferred to serve as a reporting group for analyte to avoid the influence of background fluorescence (below 500 nm).In this dissertation, starting from N, N-Diethyl-3-aminophenol and o-phthalic anhydride, six rhadamine B-schiff base derivatives were designed and synthesized. Firstly, RHB was successfully synthesized through ring formation reaction, and then RHB-B was obtained in base solution. RHB-HD was synthesized through condensation reaction between RHB-B and hydrazine hydrate, and then reacted with a series of aldehydes to form six rhadamine B-schiff base derivatives:RHB-Sal, RHB-pMOSal, RHB-NSal, RHB-ThA, RHB-PyA, RHB-ImA. The structure of all rhadamine B-schiff base derivatives were characterized by the Fourier transform infrared (FT-IR) spectra, Mass spectra (MS) and proton nuclear magnetic resonance (1H NMR) in detail.The sensoring properties of Rhodamine B-schiff base derivatives for anion were firstly studied by fluorescence and UV absorption spectroscopy, and the conditions for selectively sensoring anions were investigated. The results showed that all rhadamine B-schiff base derivatives can selectively sensoring Cr2O72- except for RHB-ImA.The sensoring properties of Rhodamine B-schiff base derivatives for cation were then studied by fluorescence and UV absorption spectroscopy. The results showed that RHB-pMOSal and RHB-NSal can selectively signal Cu2+ Furthermore, the comparison experiment was conducted to compare the sensing sensitivity of RHB-Sal, RHB-pMOSal and RHB-Nsal for Cu2+. The results indicate that the introduction of electron withdrawing group into the benzene ring of salicylaldehyde favor the sensitivity for sensoring Cu2+.
Keywords/Search Tags:rhodamine B, schiff base, fluorescence molecular probe, anions, metal ions, sensor
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