Synthesis and Structure of Pillar[<i>m</i>]arene[1]phthalimide and Pillar[<i>m</i>]arene[1]naphthalimide

A series of monofunctionalized pillar[<i>n</i>]arenes skeleton macrocycles pillar[<i>m</i>]arene[1]phthalimide and pillar[<i>m</i>]arene[1]naphthalimide (<i>m</i> = 4–6) were synthesized successfully through fragment coupling cyclization in a one-pot reaction. The introduction of pyromellitic diimide and naphthalene diimide units into the pillar[<i>n</i>]arenes skeleton not only disturbs the symmetry of the pillar[<i>n</i>]arenes but also changes their self-assembly behavior in the solid state. This functionalization approach greatly expands the structural diversity of the pillar[<i>n</i>]arenes.