Mechanically induced pyrogallol[4]arene hexamer assembly in the solid state extends the scope of molecular encapsulation.

Pyrogallol[4]arene hexamers are hydrogen-bonded molecular capsules of exceptional kinetic stability that can entrap small molecule guests indefinitely, without exchange, at ambient temperatures. Here, we report on the use of a ball mill to induce self-assembly of the capsule components and the guests in the solid state. Stoichiometric amounts of pyrogallol[4]arene and a guest, which can be an arene, alkane, amine, or carboxylic acid, were milled at 30 Hz for fixed durations, dissolved, and characterization by NMR.