Supramolecular Exchange Reaction in the Cavity of Naphthalene Diimides Extended-Pillar[6]arene.

A new naphthalene diimides extended-pillar[6]arene 1 with a large cavity and rich host-guest complexation properties was synthesized in high yield. It can not only form 1 : 2 complexes with large size polycyclic aromatic hydrocarbons but also form 1 : 1 : 1 ternary complex with perylene and 2,7-diazapyrenium. Moreover, the supramolecular exchange reaction from a 1 : 2 host-guest complex 1 ⋅ (G3) formed by 1 and perylene to a 1 : 1 : 1 ternary complex 1 ⋅ G3 ⋅ G5 formed by 1 with perylene and 2,7-diazapyrenium salt was also investigated by H NMR experiments as well as theoretically calculations.