Synthesis of Nanocup Molecules Constructed by Macrocyclization on Triptycene Platform

Abstract We describe the synthesis of nanocup molecules by using triptycene as a rigid three-dimensional template that preorganized three benzanilide-based pillars for intramolecular macrocyclization. Triple Suzuki coupling, Rh-catalyzed [2+2+2] cycloaddition, and triple olefin metathesis each furnished macrocyclic ring closure at the pillar termini, affording well-defined cup-shaped architectures. X-ray crystallography confirmed the formation of rigid nanocups with characteristic depth, aperture, and axial chirality arising from oriented amide carbonyl groups. The template-based approach enables controlled construction of cyclo-ortho,meta-phenylene and cyclophane frameworks, demonstrating that the triptycene platform preorganizes the reactive sites and facilitates the formation of defined macrocyclic architectures. These nanocup structures provide a new class of three-dimensionally preorganized aromatic macrocycles.