N-Embedded Cubarene: A Quadrangular Member of the Macrocycle Family

Despite the large number of synthetic macrocycles, the cubarenes, the quadrangular-shaped macrocyclic arenes, remain less investigated, possibly due either to synthetic challenges or to the lack of suitable building blocks. In this paper, a N-embedded cubarene (cub[4]indolocarbazole) is facilely synthesized by FeCl3·6H2O-catalyzed cyclization in dichloromethane. The endo cavity of cub[4]indolocarbazole can bury quaternary ammonium salts in an intramolecular manner, whereas the intermolecular interaction between its exo walls with Cu2+ generates two-dimensional supramolecular tessellation.