Doctor of Philosophy (PhD)



Document Type



Chapter 1 presents a concise introduction to porphyrins, especially on the synthesis of meso-tetraphenylporphyrins, which were synthesized during the course of my research and were used for further purposes in the following chapters. Chapter 2 describes the synthesis of a series of cobaltacarborane-porphyrin conjugates for the boron neutron capture therapy (BNCT) of tumors. Using an efficient and high yield ring-opening reaction, N-substituted porphyrins were also synthesized. The spectroscopic and structural properties of these compounds are presented. These high percentage boron and amphiphilic compounds are promising boron delivery agents for BNCT (prelimary cellular studies using some of these compounds have been performed). In Chapter 3 a new efficient route to synthesize a series of novel carboranylporphyrins is successfully developed, using Suzuki couplings on either the β or meso positions of porphyrins. Furthermore, efficient one pot syntheses of carboranylporphyrins and carboranylchlorins are reported. Chapter 4 reports the development of a new efficient synthetic route to a series of novel carboranylpyrroles and carboranylthiophenes. Those novel monomers were found to form polymers with extremely high thermal and electrochemical stability. Chapter 5 introduces oxacalixarene as a novel spacer to efficiently build cofacial bisporphyrins and higher oligomers. This is a general method to build a variety of cofacial architectures. The spectroscopic and structural properties of these new compounds are presented. The resulting porphyrins and their metal complexes are good models for studying energy transfer mechanisms and can also find application in the area of multi-electron redox catalysis. Chapter 6 reports a new efficient synthetic route to carbohydrate-porphyrin conjugates.



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Committee Chair

M. Graca H. Vicente

Included in

Chemistry Commons