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

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 pi-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 center dot center dot center dot 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.

Automated summary

A bowl-shaped molecule can be formed by condensing a triscationic hexaaldehyde compound and dihydrazide linkers in water. The molecular bowl has a platform with a pi-electron deficiency and a hexagonal rim with acylhydrazone functions. In the presence of chloride counteranions, the molecular bowl undergoes dimerization through N-H···Cl hydrogen bonds, forming a cage-like dimer. The cavity of the molecular bowl can accommodate a hydrophobic guest, such as 1-adamantanecarboxylic acid, in aqueous media.