Synthetic approaches to rigid "rod-and-panel" macrocycles

Timothy Newhouse

Document Type Dissertation/Thesis


This thesis reports a synthetic approach to a variety of macrocycles comprised of anthracene, phenylene, and ethynylene subunits. Most examples have ethynylene rods spacing the aromatic groups and others are spaced solely by aromatic panels. These purely hydrocarbon compounds exhibit interesting architectures with cavities governed by their connectivity to the central phenylene rings. The synthetic approach to these macrocycles utilizes a variety of cross-coupling procedures, most notably Suzuki and Sonagashira couplings, from readily synthesized dihalide and diethynyl anthracene precursors.