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Synthesis And Properties Of Rosamine-based Fluorescent Probe Molecules

Posted on:2017-04-19Degree:MasterType:Thesis
Country:ChinaCandidate:J Y ChengFull Text:PDF
GTID:2271330485987032Subject:Organic Chemistry
Abstract/Summary:
Rosamine fluorophores which is belonged to rhodamine derivatives, was obtained by the reaction of the different benzaldehyde and 3-(diethylamino)phenol. A single product was generated in this reaction. Rosamine fluorophores avoid the fluorescent quenching of rhodamine lactonic form in aprotic solvent. The maxima absorption of rosamine dyes is at about 550 nm, which is characteristic of this kind of compounds, and the fluorescence emission of rosamine dyes was found at the 570–590 nm range.In this work, RosN3, RosCHO, RosBQ, RosBr-NO2, RosCH3-NO2, RospH,RosPG and RosGSH(eight rosamine compounds) were designded and synthesized.Their structures were characterized by 1H NMR, 13 C NMR, IR and HR-MS. After a series of absorption spectra and fluorescence emission test, good performances of rosamine dyes were applied in cell imaging.In the target compounds, RosN3, as H2 S selective fluorescent sensor in DMF/ PB( 6 : 4 v/v,10 mM, pH = 7.4) solution, based on H2S-mediated reduction of azides to amines, lead to fluorescence quench by the photo induced electron transfer process(PET) which was characteristic of high selectivity toward H2 S over other competitive analytes. The probe RosN3 was successfully applied to the detection of H2 S in MGC-803 cells. A turn-on probe RosCHO, was found to be selective for HSO3- over other common anions in the Tris-HCl(10 mM)solution according to the nucleophilic addition to formyl group. The probe RosCHO was effective for HSO3- detection in living cells. The RosBQ can sense ClO- in PB buffer solution(10% CH3CH2OH) and living cells. The probe RospH was developed for selective sensing of protons. The fluorescence sensor RosGSH can detect thiols in an aqueous solution.
Keywords/Search Tags:Rosamine, Fluorescent probe, H2S, HSO3-, ClO~-
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