The conversion of curved benzenoid units into polycyclic aromatic hydrocarbon (PAH) units represents a strategy for the bottom-up chemical synthesis of carbon nanotubes (CNTs). Macrocyclic carbon nanohoops, known as cycloparaphenylenes (CPPs), containing curved aromatic rings have been synthesized, however, their conversion into PAH segments of CNTs has been challenging. CPPs represent the smallest possible horizontal segment of CNTs and are, in principle, ideally suited as diameter defining templates for the synthesis of monodisperse CNTs. This presentation will discuss the use of oxidative aryl coupling reactions in facilitating the pi-extension required to convert curved benzenoid units into curved PAH units.

Longitudinal pi-extension of strained benzenoid macrocycles to PAH-containing macrocycles

256th National Meeting (2018)

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