Adaptive nitrogen-containing buckybowl: a versatile receptor for curved and planar aromatic molecules

Abstract

Bowl-shaped polycyclic aromatic hydrocarbons (PAHs), or buckybowls, are renowned for their unique structures and physicochemical properties, making them promising fragments for functional materials. While well-known examples like corannulene and sumanene demonstrate their potential, synthetic challenges have limited the development of other fullerene fragments. Recent advancements, particularly the incorporation of heteroatoms, have expanded the structural diversity of buckybowls. In this study, we report the synthesis of a novel nitrogen-containing buckybowl (1) using the core-periphery strategy that connects two half-bowls via a single carbon–carbon bond, followed by peripheral stitching. This molecule features two nitrogen atoms within its bowl-shaped framework, representing a significant advancement in structural diversity. Compound 1 exhibits intense red emission with high color purity and quantum yield in solution. Additionally, it possesses adaptive curvature adjustment and shows excellent binding affinity to the curved PAH corannulene, the spherical PAH C₆₀, as well as the planar PAH pyrene. These versatile assembly capabilities highlight its potential applications in supramolecular chemistry and materials science, paving the way for advancements in molecular electronics and photonics.