The Synthesis And Investigating Of BODIPY-indanedione Fluorescent Dyes

Over the past twenty years, boradiazaindacenes (4,4’-difluoro-4-bora-3a,4a-diaza-s-indacene,BODIPY) dyes have attracted considerable attention due to its bright emission. Excellent photochemistryand photophysics properties, such as large molar extinction coefficients, outstanding fluorescence quantumyields, good photostability, less sensitivity to pH have been established. And the variation of opto-physicalproperties can be realized by structural modification of BODIPY framework. Also, BODIPY has beencondidered as one of the most promising fluorescent dyes that can satisfy the requirement of pH, ion, ormolecular probes, switch devices, and dye-sensitized solar cells (DSSCs) etc. Unceasing efforts were exerton the investigation of BODIPY derivatives. In this dissertation, a series of new BODIPY derivatives weredesigned and synthesised, based on BODIPY framework with the emission color varied from green toyellow. Their basic photophysics properties were investigated intensively.In chapter one, the development of BODIPYand relvant fluorescent dyes were reviewed. According tothe mechaism of fluorescence, several typical fluorescent dyes were introduced in the field of applicationand development. Based on the application and development of new materials, an creative idea was putforward.In chapter two, a series of novel BODIPY derivatives were synthesized and fully characterized.Different type substituents were introduced to the8-phenylBODIPY framework, including electron donorgroup (-OMe,-N(Me)2), electron acceptor goupr (-CN, NO2, X), and bulky substitutends (-Ph3N, Pyrene).The effects derived from different substitutents were fully investigated. The synthesis was mainly focusedon condenstation and rearragement between BODIPY and1,3-indaneone. With the BODIPY and theindaneone condensed and bonded by double carbon carbon bond, the fluorescence of BODIPY derivativeswas effectively quenched. Only strong absorption peak around555nm observed, without detectableemission singal founded. Once the rearrangement occurred between methyl unit of BODIPY and themethylene unit of indaneone, the emission of BODIPY derivatives was recovered with the peak locatedaround575nm and high quantum yield. Apart from the N-alkyl substitutents attached to the8-phenylBODIPY derivatives, most of the synthesized BODIPY derivatives exhibited bright fluorescencein toluene. Detailed absorption, emission spectal were provided in the main text.Further condenstation with aromatic aldehyed were carried and the products were obtained andcharacterized. There compouds exhibit highly senstivety towards F-and H+. Detailed data were provided inthe text. Possible mechanism was given based on the literature report and supported by ptoton NMRtitration.In chapter three, a conclusion was given based on the experimental data.