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A Cyclophane-Based Approach to Highly Strained [n]Cycloparaphenylenes and Synthesis of Hexa-substituted Pyrenes and Their Application to Polycyclic Aromatic Hydrocarbon Synthesis




Wang, Mengzhou

Type of Degree

PhD Dissertation


Chemistry and Biochemistry


Chapter 1: The synthesis of highly strained carbon nanoring, [4]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 [4]CPP derivative and [5]CPP as well as several intermediates as the potential precursors for [4]CPP derivative and [5]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.