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

Chem Asian J. 2024 Oct 16;19(20):e202400767. doi: 10.1002/asia.202400767. Epub 2024 Sep 12.

Abstract

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)2 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 1H NMR experiments as well as theoretically calculations.

Keywords: host-guest chemistry; naphthalene diimides; pillar[6]arene; supramolecular exchange reaction.