Synthetic Methods Towards Strained Aromatic Nanohoops and their Application in Electronics
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Carbon nanohoops represent an interesting and exciting structural motif with many potential material applications. To this end we have developed design several synthetic strategies to access a wide variety of functionalized hoops. Chapter I outlines the current state of the “Nanohoop” field focusing on the size-dependent properties of -cycloparaphenylene. This introduction walks through the interesting properties highlighting several interesting phenomena associated with nanohoops including their photophysical and electronic properties. To appreciate these properties it is necessary to understand the synthetic advances that lead to their fundamental understanding. Chapter II outlines the original size-selective synthesis of -cycloparaphenylene and their fluorescence quantum yields. Chapter III describes the seminal synthesis of the smallest nanohoop to date, CPP utilizing a series of mild reactions. In Chapter IV, the key step from this synthesis was expanded into a strain building coupling strategy not only for the synthesis of nanohoops but also for natural products. With scalable strategies available, we designed a series of nitrogen doped nanohoops in the pursuit of true donor-acceptor systems as a means to tune the electronics of nanohoops. Chapter V details the design principals that were uncovered and highlight the unique properties that can only be achieved in the nanohoop scaffold.