Late-Stage Transformations of Cycloparaphenylenes

Abstract

Exploring the synthesis and properties of non-planar aromatics is an important endeavor, as technology is often advanced when new structures and materials are realized. The Jasti lab specializes in making cycloparaphenylene (CPP) derivatives, which are highly strained aromatic macrocycles with valuable properties accessible via precise synthetic control. This dissertation focuses on late-stage transformations of CPPs decorated with versatile functional groups. Late-stage transformations allow for efficient synthesis of a wide variety of derivatized CPPs. Herein we focus on utilizing fluorinated and alkyne-containing CPPs to make novel extended structures. Structures of interest include metalated CPPs, redox-active CPPs, novel guest-host CPP-fullerene complexes, and trimeric CPPs. This work applies well-studied reactions that have been investigated on planar aromatics to the growing field of CPP chemistry.