Date of Award
Doctor of Philosophy
Photochemistry and photophysics are two rapidly expanding areas in science. The first part of this dissertation looks at the synthesis of a new fluorescent probe based on the well-known fluorophore nitrobenzoxadiazole (NBD). We synthesized a new derivative using the nitrile functional group as the electron withdrawing group. Our results showed our fluorophore (CBD) displayed redder emission than the nitro counterpart, and an emission range that was similar to that of the sulfonamide containing derivatives. Additionally CBD displayed extensive solvatochromic properties: high quantum yield and bluer emissions in nonpolar solvents while low quantum yield and redder emissions as the solvent polarity increased.
The second part of this dissertation looks at the extensively used photocleavable protecting group (PPG) ortho-nitrobenzyl. We synthesized a new derivation of the ortho-nitrobenzyl PPG which demonstrated photocleavable properties which could be tuned by adjusting the solvent. Photocleaving reactions were observed in nonpolar solvents while no photocleaving reactions were observed in polar solvents. Work is currently underway to better understand this PPG.
Thooft, Andrea, "Manipulating push-pull systems to probe biology and photochemistry" (2018). Graduate Theses and Dissertations. 16678.