Self-Assembly of a Purely Organic Bowl in Water via Acylhydrazone Formation

Abstract

A bowl-shaped molecule can be self-assembled by condensing a triscationic hexaaldehyde compound and three equiv. of a dihydrazide linkers in pure water. The molecular bowl is thus composed of a triscationic π-electron deficient platform, as well as a hexagonal rim that contains six acylhydrazone functions. When the counteranions are chloride, the solid-state structure reveals that this molecular bowl undergoes dimerization via N–H···Cl hydrogen bonds, forming a cage-like dimer with a huge inner cavity. This molecular bowl can employ its cavity to accommodate a hydrophobic guest, namely 1-adamantanecarboxylic acid in aqueous media.

Keywords

• self-assembly
• dynamic covalent chemistry