Doctor of Philosophy (PhD)
ABSTRACT Chapter 1 describes the most stable isomer of porphyrin called porphycene. In this chapter photodynamic therapy (PDT) is explained, and the application of porphycenes in PDT is also described. Other biological applications and its uses in catalysis are also summarized here. The general chemical reactions of porphycenes are also explained. Chapter 2 involves the synthesis of pyrroles and bipyrroles. Functionalization of pyrrollic substituents is demonstrated using organometallic coupling reactions like Stille coupling and Grubbs olefin metathesis. The synthesis of divinyl bipyrroles is intended to provide an important precursor to porphycene synthesis via ring closing metathesis using Grubbs catalyst. Chapter 3 describes the synthesis of new 5,5’-dimethyl-2,2’-bipyrrole. The methyls at the alpha-position of the pyrroles are reactive and are shown to be susceptible to halogenation, acetylation and oxidation reactions, giving new useful products for the synthesis of various porphyrinoids. Chapter 4 explains the new approach towards porphycene synthesis via the synthesis of benzo-bridged 1,2-di(2-pyrrolyl)ethenes. Named coupling reactions like Ullmann, Suzuki, and Sonogashira, were performed on pyrrole derivatives. The synthesis of other possible porphyrinoids was also attempted.
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Ihachi, Moses Inyanje, "New strategies for the synthesis of porphyrinoids" (2013). LSU Doctoral Dissertations. 3186.
Smith, Kevin M.