Periphery-Core Strategy to Access a Bowl-Shaped Molecule Bearing Multiple Heteroatoms

Most of the bowl-shaped molecules are synthesized via a core-periphery strategy with the bowl rim closed at the final stage. However, the construction of heteroatom-doped buckybowls by the periphery-core method with the bowl bottom sealed by inserting new atoms in the last step is quite limited. Herein we report the synthesis of a bowl-shaped compound containing four sulfur atoms and two embedded N-B bonds with the ratio of carbon atom and heteroatom as low as four through a periphery-core strategy. Crystallographic analysis confirms the formation of a bowl-shaped structure. The multiple heteroatoms alter the molecular electronic structure, thus resulting in the distinct aromaticity when compared with its all-carbon congener. The electron-rich buckybowl shows a strong interaction with the electron-deficient fullerene C₆₀ by forming a 1 : 1 complex in toluene.