Synthesis of Small, Chiral, and Photoswitchable Cycloparaphenylenes
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Cycloparaphenylenes (CPPs) represent the unit-cycles of conductive armchair carbon nanotubes (CNTs). In addition to their utility for the bottom-up synthesis of CNTs with discrete diameter and chirality, these strained hydrocarbon macrocycles have attractive properties of their own for material science and organic electronics. Herein I report research focused on advancing the synthetic technology behind CPPs, culminating in the synthesis of CPP, the smallest and most highly-strained member of the CPP series to date, as well as the derivitization of the CPP platform to include chiral nanohoops with a spiral carbon backbone and photoswitchable nanohoops based on azobenzene incorporation into the CPP architecture. The synthesis and characterization of CPP, 1,5-naphthylCPP, azoCPP, and azoCPP are reported along with advanced intermediates towards rotationally restricted 2,6-naphthylCPP and preliminary photoisomerization results for azoCPP and azoCPP. This dissertation contains both previously published and unpublished co-authored material.