Smith, Amos, BMicikas, Robert, John2023-11-222023-11-2220232023https://repository.upenn.edu/handle/20.500.14332/589722023Fluorescent amino acids (FAAs) offer significant advantages over fluorescent proteins in applications where the fluorophore size needs to be limited or minimized. A long-sought goal in biological spectroscopy/microcopy is to develop visible FAAs by modifying the indole ring of tryptophan. In Chapter 1 of this thesis, I discuss the investigation of the absorption spectra of a library of 4-substituted indoles and find that the frequency of the absorption maximum correlates linearly with the global electrophilicity index of the substituent. In Chapter 2, a scalable synthesis of Fmoc-protected blue fluorescent amino acid, L-4-cyanotryptophan (W4CN), exploiting an enantioselective phase-transfer catalyzed alkylation is presented. Finally, in Chapter 3, Large-Scale Synthesis and Assessment of the Potential Thermal Hazards of 3,6-dichlorotetrazine (DCT) will be discussed.enChemistryDissertation/Thesis2023-11-22