Design, Synthesis, And Spectroscopic Properties Of Bodipy-Based Fluorescent Thiophenols Sensor And2-(2’-Hydroxy-Phenyl)Benzothiazole Derivatives

Among many of the fluorophores, boron-dipyrromethene (BODIPY) fluorescent dyes have been recognized as the promising ones for the labeling reagents, fluorescent switches, chemosensors, non-linear optical materials, and photovoltaics because of their outstanding characteristics, such as high molar absorption coefficients, intense fluorescence quantum yield, valuable photo-and chemo-stability, and exceptional insensititivity to the polarity of solvents as well as to pH. The addition of near-infrared (NII) absorbing/emitting property to the BODIPY dye makes BODIPYs more useful materials in applications in solar cells as well as biolabeling. Hence, various methods to access NIR BODIPY dyes have been developed, including extension of^-conjugation, introduction of intramolecular charge transfer (ICT) character, and incorporation of a nitrogen atom in the skeleton. High rigidity of π-systems leads to a high fluorescence quantum yield in solution as well as strong intermolecular π-π interactions in the solid state, which are beneficial for applications as π-functional materials. Herein, we have designed and synthesized a series of BODIPY and aza-BODIPY dyes,12,13,14,15, which were rigid by six-membered ring or five-membered ring. In chapter two, the effects of nitrogen atom in the skeleton and rings in the spectroscopic properties of dyes were discussed by UV-vis absorption fluorescence spectra in solution and solid film. And a highly selective and sensitive turn-on red fluorescent BODIPY-based probe1with high off-to-on contrast ratio has been developed. Among the reported thiophenols probes, Ru (II) complexes and indole-based boron-dipyrromethene (BODIPY) emit in red region, however the off-to-on ratio is not optimal. Herein, we report a novel probe1based on1-amine substituted BODIPY for discrimination of thiophenols over aliphatic thiols sensitively. The detection limit for PhSH reaches4×10-6M measured in acetonitrile/PBS buffer. And the detection of thiophenols was able to be conducted in water when1%Tween20was used and the sensitivity was further improved with the detection limit to37nM. Moreover, probe1is a useful fluorescent probe for detecting thiophenols in living cells in red emission which may greatly improve the detectable sensitivity.Some fluorophores, such as BODIPY, incorporating a four-coordinated boron bound to a π-conjugated chelate have emerged as very promising due to their outstanding chemical and photophysical properties.2-(2’-Hydroxyphenyl)benzoxazole (HBO) and2-(2’-Hydroxy-phenyl)benzothiazole (HBT) derivatives are an interesting class of fluorophores due to their intrinsic Excited-State Intramolecular Proton Transfer (ESIPT) property. π-conjugated aromatic systems coordinated to BF2or BPh2have received widespread interest for their use in electroluminescent devices. In chapter three, we have designed and synthesized HBT16with ESIPT and BF2, BPh2, B(PhOHNC)2HBT17,18,19and we explored the effect of size of groups on B atom in the the properties of liquid and solid film.