The Optimized Design,Synthesis Of BODIPYs And Theirs Application In NIR Fluorescent Probes

Fluorescent probes can transfer molecular recognition events into visible fluorescence signals,which have the virtues of noninvasive,high sensitivity,real time and convenient.The development in fluorescent probes has become a popular research field research field,especially probes for pH,viscosity,anions,toxic cations in environment and in vivo,DNA etc.Based on this,this thesis designed and synthesized a series of near-infrared BODIPY dyes,which spectroscopic characteristics were systematic studied.And the hydrophobin was adopted to improve BODIPYs' abilities of solubility and membrane permeability.The specific details are as follows:(1)The strong electron-donating groups were introduced to the 3-and 5-methyl sites through the Knoevenagel reaction.And the decyl was introduced to BODIPY through carbazole to enhance its solubility in non-polar solvents,which facilitated preparation and characterization this derivative.With these steps,the BODIPYs' emission wavelengths red shift about 100 nm at most.And the stokes shifts also gained about 80 nm.(2)Through the studies of the optical properties upon pH value,it was proved that BODIPYs display pH non-sensitive characteristic,which was helpful to be applied in biological system.(3)For the first time,we provide a new strategy for the rapid and efficient production of a water-soluble and membrane-permeable dye by mixing with an amphiphilic protein named hydrophobin that separated from nature.And the method was rather simple and straight.Furthermore,hydrophobin functionalized BODIPY are toxicity free to cells.The hydrophobin-BODIPY complex could pass through both the cell plasma membrane and nuclear membrane efficiently.