Design, Synthesis And Application Of The Quinoline Derivatives/Novel FRET Platform

Small organic molecule fluorescent dye as an important component of the dyeinside the field, it has been widely used in the detection of ions, enzyme analysis, cellimaging, various functional materials and so on. Fluorescent probe because of its highsensitivity, high selectivity and easy testing operation process, experimentalreproducible, biological compatibility, and many other advantages, it has beenwidespread concern scientists. Therefore, many of small organic molecule fluorescentprobes with high sensitivity, good selectivity have been reported in recent years.In this thesis, we first studied the chromenoquinoline derivatives. The maincontents are as follows:(1) The Stokes shift, in order to obtain a larger Stokes shift value ofchromenoquinoline derivatives, we design effects by using the principle of ICT inchromenoquinoline. Introduction of electron donor group and electron withdrawinggroups to form a fluorescent group containing ICT effect obtained compound9, itsStokes shift extend as long as132nm.(2) Fluorescence quantum yield, chromenoquinoline-nitro derivatives, because ofthe fluorescence quenching effect of nitro group, the quantum yield of compound4and compound5is very low. In order to improve the quantum yield, obtained thechromenoquinoline-amino derivatives compound10and compound11by reduction ofthe chromenoquinoline-nitro derivatives. Experimental results show that thefluorescence quantum yield of compound10and compound11is very high.(3) The pKa value, the electron donating group can increase the electrondensity of the compound, i.e, by increasing the electron donating group can improvethe alkaline of chromenoquinoline’s nitrogen atom, so as to achieve the purpose ofincreasing their pKa values. By this design, we obtain compound6and compound11,their pKa values were increased to4.38and6.27. The pKa value of the compound11has been completed to meet the application of the cell imaging.In the second work of this thesis, in order to solve the difficult separationproblem of the second-generation coumarin-Rhodamine FRET isomer, we adopted the3-(1-piperazinyl) phenol as a raw material for the synthesis of Rhodamine, only oneproduct to create a single rhodamine. This structure of Rhodamine have a piperazinylgroup which can be used as the connecting arm, so that a solution of the second generation of rhodamine isomers difficult separation problems, while also shorteningFRET platform synthesis step. We designed and synthesized the third-generationcoumarin-Rhodamine FRET-based platform by this program. To confirm that thethird-generation of coumarin-Rhodamine FRET-based platforms practicality, wefurther designed and synthesized copper ion probe. Experimental results show that thecopper ion probe based on the third-generation of coumarin-Rhodamine FRET can besuccessfully applied in cell imaging.