Synthesis And Applications Of Bodipy And Other Functional Organic Compounds Based On Intramolecular Charge Transfer

In the past two decades, boron dipyrromethene (BODIPY) dyes by its excellent photophsical features and chemical stability, have been attracted more and more attention about its synthesis and properties study, and applied in many areas of ion recognitions, optoelectronic materials and biomolecular labels. Dye-sensitized solar cells (DSSCs) have received considerable attention in many solar cells because of the simple production process, low cost and high efficiency solar cell. In this paper, a series of BODIPY dye functional orgainic compounds were designed and synthesized, which were applicated in DSSCs and gold-ion fluorescent probe.We have synthesized novel Bodipy-based sensitizers (B1-B3), composed of triphenylamine moiety as electron donor and cyanoacetic acid as electron acceptor, forming D-π-A conjugated systems and being applied in DSSCs (In Chapter2). Those dyes have strong absorption in the visible-light region in both the solution and solid state. Cyclic voltammetry measurement and DFT calculation demonstrated photoinduced electron injection from the excited dyes into the conduction band of TiO2and intramolecular charge transfer, respectively. We found that the performance of the cells based on those dyes varies much with the substituents at8-position of Bodipy. The introduction of the pentyl moiety at8-position of BODIPY in dye B3achieves the best photovoltaic performances, which the solar energy conversion efficiency up to1.83%. This design strategy has offered some useful tips for development of more efficiency novel solar cell based on BODIPY derivatives.In Chapter3, four novel quinoline dyes (Q1-Q4) containing distinctive strong electron-donating groups including N,N-diethyl, diphenylamine, methyloxl-modifled carbazole and dibutoxyphenylamine, quinoline as π-bridge and cyanoacetic acid as electron acceptor form D-π-A conjugated syste, are synthesized and applied in DSSCs. A series of chractertic tests including the photophysical, electrochemical and photovoltaic properties of those dyes were investigated. The turning of HOMO and LOMO energy level of dyes can be conveniently accomplished by alternating the donor moiety. The DSSCs based on dye Q4with dibutoxyphenylamine as electron-donating showed the best photovoltaic performance:an over all conversion efficiency as3.07%.In Chapter4, we have designed and synthesized a novel gold-ion-responsive fluorescent probe1. The aniline moiety in fluorescent probe1was converted to phenanhridine by the gold-catalyzed intramolecular hydroamination, resulting in blocking the intramolecular PET process and emitting a strong green fluorescence. The fluorescent probe possesses a short response time and a low detection limit. This is the first time a fluorescent probe for gold ions has been constructed by the way of adjusting PET process in BODIPY dyes through gold-catalyzed intramolecular hydroamination.The Competition of Paterno-Buchi (PB) reaction with triplet-triplet energy transfer (ET) in the photochemical reaction of5-fluoreuracil (FDMU) and Benzophrnones derivatives (BPs) was investigated in Chapter5. We found the BPs triplet energy and the reaction temperature affects the competition. The triplet-triplet energy transfer is dominated when in the higher triplet energy of BPs and higher reaction temperature; on the contrary, PB reaction is dominant.