Doctor of Philosophy (PhD)



Document Type



An overview of BODIPYs history, basic structure, electronic properties is described. Additionally, their attribute of tenability in their photophysical and electronic properties has been discussed. Lastly, their application in the biomedical field as bio imaging, labeling, chemo sensors and photosensitizers are also discussed. In Chapter 2, a library of meso- Pyridyl and meso pyridinium BODIPY dyes was designed, synthesis and comparison on their photophysical, electrochemical and cytotoxic studies done. From this study chlorine atoms at the 2, 6 positions was shown to enhance their relative fluorescence quantum yields in different organic solvents and water. In chapter 3, 8(meso)-pyridyl-BODIPYs with a 2-, 3-, or-4-pyridyl group and electron-withdrawing groups at either the 2- or 2, 6-positions were synthesized, and their structural and spectroscopic properties investigated. 2, 6-methyl ester groups increased the relative fluorescence quantum yields of these derivatives. The introduction of a 2-nitro substituent on the 8(meso)-pyridyl-BODIPYs induced significant hypsochromic shifts, and decreased their relative fluorescence quantum yields while Introduction of a chlorine atom was shown to reduce the polarity of the molecules and induce pronounced bathochromic shifts, with partially fluorescence restoration. Chapter 4 is a discussion on the design and synthesis of several BODIPY derivatives with different substituents. BODIYs with 1, 3, 5, 7- tetra methyl substituents and meso –aryl-groups are shown to have high fluorescence quantum yield due to prevention of rotation. Some of the BODIPYs synthesized in this chapter were post functionalized in chapter 5.In chapter 5, a BODIPY nitration protocol was discussed. The use of nitronium tetra fluoroborate in sulfolane as the nitrating agent afforded mono and dinitro depending on the equivalents added, the reaction time and the electron density of the BODIPYs. Different BODIPY positions were nitrated selectively. Their spectrophotometric studies were performed and discussed.



Committee Chair

Vicente, Graca

Available for download on Tuesday, October 29, 2024