Synthesis and Investigation of BODIPY and Chlorin Derivatives for Material and Biomedical Applications

Abstract

Chapter 1 of this dissertation is a short introduction of the structures and properties of boron dipyrromethenes (BODIPYs). The common synthetic and functionalization methods of BODIPYs along with their general applications in material and biomedical science have been described. Chapter 2 includes the preparation of novel E-, Z-ethenyl and ethynyl-linked BODIPY dimers and the investigation of their spectroscopy properties. A facile synthetic route has been explored to specifically obtain certain configuration efficiently. Computational study from the collaborator further explained the effect of linker on the photophysical properties. This studied has also been reported in J. Phys. Chem. A 2018, 122(30), 6256-6265. Chapter 3 has described a series of boron functionalized BODIPYs with C, O, or N-substituents. The methodology optimization was carried out by screening the Lewis acid catalyst and using TMS-nucleophiles. The Nsp2-substituent was introduced to the boron position for the first time. Along with highly tunable fluorescence quantum yield, this work resulted in a publication Inorg. Chem. 2018, 57(23): 14493-14496. Chapter 4 is based on a research on the relationship of meso-group and the spectroscopy properties of BODIPYs. Nearly quantitative fluorescence quantum yields were obtained by dual effects from the rotation restriction and chlorination. The unique rotation mechanism was disclosed by the computational study from the collaborator. This research has been published on J Porphy. Phthalocyanines 2020, 24(05n07), 869-877. Chapter 5 involves the description a serendipity in the development of chlorin e6 bioconjugate. A traditional antiHIV drug was covalently conjugated to the 131-position of chlorin e6 and showed unprecedented anticancer activity. This discovery has recently been accepted by J Porphy. Phthalocyanines.