Synthesis And Characterization Of New Boron-dipyrromethene Dyes

Boron-dipyrromethene(BODIPY) dyes have been widely investigated and applied as fluorescent probes and biological imaging agent due to their excellent optical properties. In this thesis, a series of BODIPY precursors bearing one, two or three hydrophobic chains were synthesized using 2-methyl pyrrole and aromatic aldehyde as starting material. These precursors were further modified by introducing the quaternary ammonium moieties to the boron atom. These new compounds were characterized by NMR spectroscopy, mass spectroscopy and element analysis. The optical properties of the dyes were studied by UV/Vis absorption and fluorescence spectroscopy in various solvents. The effects of solvent polarity on the spectroscopic properties of the amphiphilic BODIPYs were investigated. Furthermore, the study on aggregation behavior of the amphiphilic BODIPYs in water indicates that the dye bearing three hydrophobic chains aggregates strongly even at concentration as low as 10-6 M. Based on these results, the synthesis of novel amphiphilic photochromic BODIPY dyes were explored through Stille and Suzuki coupling reactions. Further optimization of the reaction conditions is still needed to obtain the target compounds.