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Design And Synthesis Of High Quantum Yield Bodipy Dyes And Their Fluorescent Property

Posted on:2014-02-07Degree:MasterType:Thesis
Country:ChinaCandidate:C T XiaoFull Text:PDF
GTID:2231330395483205Subject:Applied Chemistry
Abstract/Summary:PDF Full Text Request
In recent years, the4,4’-difluoro-4-bora-3a,4a-diaza-s-indacene (Bodipy) and their derivatives have been one of the most extensively studied topics due to their kinds of advantages, such as mainly nanosecond lifetimes, fluorescence with sharp and narrow peaks, high quantum yields, high molar absorption coefficients, and reasonable stability under physiological conditions and so on. Therefore they’re widely applied in many fields such as light-harvesting systems, biological probes, supramolecular fluorescent gels, solar cells, and ion sensing and signaling. Nowadays more and more attentions have been paid in their structural modification in order to tune their fluorescence properties. These modification methods are,1) replacement of a C atom at the meso-position by a N atom,2) extension of the π-electron conjugation by introduction of active methyl structures,3) introduction of electron-donating moieties, and4) the extension of the π-electron conjugation by introduction of aryl moieties. In particular, the introduction of aryl moieties was considered to be the best way to extend the π-electron conjugation.In this thesis,2-(2-iodophenyl)-4-phenyl-lH-pyrrole (compound6) was synthesized, as a raw material,3,5-di(2-iodophenyl)-1,7,8-triphenyl F-Bodipy (compound7) was synthesized. AzaBodipy,3,5-di(2-iodophenyl)-1,7-diphenyl F-Bodipy (compound12), was synthesized at the same time. And through the Suzuki cross-coupling reaction, Sonogashira cross-coupling reaction and C-H activity to modify them, in order to obtain a series of new Bodipy derivatives.The ultraviolet absorption spectrum and fluorescence spectrum of some products were measured, and their fluorescence quantum yields were calculated. The results indicated that compound11possessed superiority maximum absorption wavelength,663nm. The excitation and emission spectra of each compound indicated that the excitation wavelength of compound11had a certain red-shift compared with compounds7a,7b,8a,8b,9a,9b,10a and10b. While the absorption wavelength of AzaBodipy ring-closed production (compound14) had a significant blue-shift compared with compound12, its fluorescence quantum yield had been greatly increased through introducing a large π-electron conjugated system, such as phenyl (compound8a,8b, the fluorescence quantum yield, respectively0.62,0.68), phenylethynyl group (compound13, the fluorescence quantum yield was0.82).
Keywords/Search Tags:Bodipy derivatives, fluorescence spectrum, transition-metal catalysis, red-shift, blue-shift
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