Synthesis and Characterization of Small Molecule Carbon Nanotube Fragments
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Cycloparaphenylenes (CPPs) can be considered the smallest possible fragment of an armchair carbon nanotube (CNT), yet they were envisioned as synthetic targets almost 70 years before CNTs were discovered. Having succumbed to total synthesis in the past decade, these strained carbon-rich macrocycles, as described in Chapter I, have emerged as both interesting materials for applications in organic electronics as well as promising candidates to seed the “bottom-up” growth of CNTs. Herein I first report methodology that has facilitated the rapid construction of CPPs from simple building blocks as well as the current limitations to access functionalized CPPs with these strategies in Chapter II. With the ability to access CPPs in unprecedented quantities, some interesting physical organic properties were revealed through oxidation and subsequent optoelectronic characterization in Chapter III. Efforts then turned towards the synthesis of more rigid CNT fragments in Chapters IV and V, resulting in the synthesis of two CPP dimers, (3,10)-dibenzo[a,h]anthracenyl-nanohoop and (2,11)-dibenzo[c,m]pentapheneyl-nanohoop. Lastly, progress towards [n]cyclophenacene, an aromatic belt, is presented. This dissertation contains both previously published and unpublished co-authored material.