Font Size: a A A

Research On A New Method Of The Synthsis Of β-formyl-BODIPYs

Posted on:2013-01-30Degree:MasterType:Thesis
Country:ChinaCandidate:W F YeFull Text:PDF
GTID:2211330371459588Subject:Materials engineering
Abstract/Summary:PDF Full Text Request
Boron dipyrrins (BODIPYs) are strongly UV-absorbing small molecules with excellent photophysical properties and photochemistry stability, such as high fluorescene quantum yields, long maximum absorption and emission wavelengths, sharp fluorescence emissions, high photophysical stability, and low sensitivity to the polarity and pH of their environment, etc. Their fluorescene profiles can be easily tuned by modifications to the structures, consequently, these molecules have found wide applications as fluorescent labels for DNA and proteins and have attracted renewed research interests as fluorescent switches, chemosensors, laser dyes, photosensitizers, energy transfer cassettes, supramolecular fluorescent gels, etc.In this thesis, twelveβ-formyl-BODIPYs and twelveβ-formyl-aza-BODIPYs were synthesized, and characterized by 1H-NMR,13C-NMR and MS. The reaction conditions were optimized.P-formyl-BODIPYs were synthesized from ethyl acetoacetate via three-step reactions. At first,2,4-dimethylpyrrole were synthesized from the reaction of ethyl acetoacetate and a-aminoketone, which was prepared from ethyl acetoacetate and sodiumnitrite, then BODIPYs were obtained through "one pot" method from the reaction of 2,4-dimethylpyrrole and different sunstituted aldehyde, finally the target compounds 2 were obtained from the reaction of BODIPY and Vilsmeier-Haack reagent.P-formyl-aza-BODIPYs were synthesized via five-step reactions. At first, condensation of acetophenone or p-methoxyacetophenone with benzaldehyde derivatives afforded chalcones by Claisen-Schmit condensation, and Michael addition of nitromethane gave the compounds 4, then condensation with ammonium acetate afforded the azadipyrromethene 5, then complexation with boron trifluoride gave aza-BODIPYs 6, finally the target compounds 7 were obtained from the reaction of aza-BODIPYs and Vilsmeier-Haack reagent.Vilsmeier-Haack reagent were prepared via interaction between N,N-dimethyl-formamide and oxalyl chloride, which is low toxic, cheap and easy to obtain. The synthesis ofβ-formyl-BODIPYs andβ-formyl-aza-BODIPYs via the Vilsmeier-Haack reaction have high yield under mild conditions.
Keywords/Search Tags:BODIPY Derivatives, β-formyl-BODIPYs, β-formyl-aza-BODIPYs, Claisen-Schmit condensation, Vilsmeier-Haack reagent
PDF Full Text Request
Related items