Synthesis And Properties Of Phenanthrene-fused BODIPYs And Meso-β Linked Bis And TriBODIPYs

In this thesis, we have investigated the design, synthesis and optical properties of phenanthrene-fused BODIPYs and the synthesis and singlet oxygen generate efficiency of a set of meso-β linked bis and triBODIPYs. These results have been detailed in the following two Chapters.In Chapter 1, we have synthesized a series of tetra- and hexaarylBODIPYs 2a-j, 3 and 4a-b from the Suzuki coupling reaction between 2,3,5,6-tetrabromo or 1,2,3,5,6,7-hexabromoBODIPYs and a set of aromatic boronic acids. These resultant tetra- and hexaarylBODIPYs were then applied for the subsequent oxidative coupling reaction to afford the desired ??phenanthrene-fused BODIPYs 3a-j. The substituent effects on this oxidative coupling reaction were investigated. The optical properties of these dyes were studied by UV-vis and fluorescence spectroscopy. These phenanthrene-fused BODIPY dyes showed maximum absorption and emission in the range of 672-740 nm(for absorption) and 688-754 nm(for emission).In Chapter 2, for the thorough investigation of the structure-property relationship, we have synthesized a set of meso-β directly linked bis(or tri)BODIPYs 2a-b and 3a-b from the β-formylBODIPYs using our previous synthetic method. Their optical properties and singlet oxygen generation efficiencies have been investigated. These meso-β bis(or tri)BODIPYs show good singlet oxygen generation efficiency, and the orthogonality of the two BODIPY units were found to facilitate the singlet oxygen generation of these dyes. Among those, the singlet oxygen yield for 2b reached to 0.96.