Study On The Synthesis,Characterization And Property Of Boron Dipyrromethene(BODIPY) Derivative And Nano-composites

Near infrared fluorescence spectroscopy and imaging are nowadays essential tools for the noninvasive study of matter or living systems in materials and life sciences,medicine,and(bio)-technology.In particular,the development of highly efficient nearinfrared fluorescence probes is of great significance in ion detection,biomolecule detection,cell imaging and tumor therapy.Boron dipyrromethene(BODIPY),have attracted considerable attention due to their intriguing physicochemical and spectral properties,including fluorescence quantum yield,good photochemical stability and biocompatibility.In addition,small modifications to their structures enable tuning of their fluorescence characteristics,consequently,these dyes are widely used to fluorescence probes,electrochemical sensing,and fluorescence imaging of biomolecules in living cells.The research progresses of synthesis of BODIPY,BODIPYs anticancer drugs and fluorescence imaging of biomolecules were systematically summarized in this thesis.Thirteen new BODIPY compounds and its based manganese complexes and ionic liquid complex composites were designed and synthesized.The structure of these compounds were characterized by ESI-MS,Elemental analysis,TEM,et al,The catalase activity of light-driven water oxidation to produce oxygen,fluorescence imaging and PDT for tumor were also studied.The innovative results are as follows:(1)Thirteen new BODIPY compounds were designed and synthesized.And then analyzed the relationship between spectroscopic properties(such as fluorescence quantum yield and life time)and structure of these compounds.The results indicate that dimethylaminostyryl caused the increase of stocks shift and enhancement of fluorescence quantum yield.The introduction of morphine group into the meso site of BODIPY could be applicated to cell imaging due to its hydrophilic and protonated.Then the toxicity of these compounds was measured,and all of the results provide a theoretical basis for the construction of cell imaging reagent.(2)A nano NIR fluorescence Mn(III/IV)polymer(PMnD)was characterized.The PMnD shows strong emission at 661 nm when excited with 643 nm.Furthermore,PMnD can catalyze water oxidation to generate dioxygen when irradiated by red LED light(10W).In particular,the PMnD can enter into HepG-2cells and mitochondria.Both anticancer activity and the inhibition of the expression of HIF-1? for PMnD were concentration dependent.(3)We have found that the protonation efficiency of morphine group is higher than is iquinoline group when comparing the pH response for three BODPY derivatives of 2d,DTM and DTP.The color of compound is visible to the naked eyes in the acid solution for pH=2.5.There is a strong insert effect between the compound and DNA,which could be applied into the targeted nucleic acid imaging of tumor cells.In addition,the fluorescence changes of DTP for turn-on make it possible to develop a new pH fluorescent probe.(4)A novel imidazolium-based ionic liquid was synthesized and assembled with DPD to obtain DPD-Ps composites.The composites could be well dissolved in aqueous solution and absorbed by cells.The enhancement of light-dark toxicity can effectively improve the suppress effect of tumor cells.Therefore,it can act as nucleic acid carrier and enter into the cells and targeted mitochondria,and it also can develop a new mitochondria targeting imaging reagent.