A Cyclophane-Based Approach to Highly Strained [n]Cycloparaphenylenes and Synthesis of Hexa-substituted Pyrenes and Their Application to Polycyclic Aromatic Hydrocarbon Synthesis
Type of DegreePhD Dissertation
Chemistry and Biochemistry
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Chapter 1: The synthesis of highly strained carbon nanoring, CPP and its potential precursor has been an ever-increasing level of interest in the past few decades. The biggest challenge in CPP synthesis is macrocyclization and aromatization. Two macrocyclization strategies have been developed for the syntheses of CPP derivative and CPP as well as several intermediates as the potential precursors for CPP derivative and CPP. Chapter 2: The synthesis of 1,2,4,5,7,8-hexasubstituted pyrene has been achieved by initially functionalization the K-region of pyrene. Bromination, borylation, and oxidation reactions afford high regioselectivity at 1,8-position, which controlled the functionalization of 2,7-position. 1,2,4,5,7,8-hexasubstituted pyrene is a valuable building block for the construction of polycyclic aromatic hydrocarbons, several pi-extension reactions have been conducted on hexasubstituted pyrene by using Suzuki-Miyaura reaction and Scholl reaction.