Suit[4]ane

Abstract

Suitanes are two-component mechanically interlocked molecules in which one (torso) of the components, with several protruding limbs, is encompassed by another (suit) all-in-one component. This kind of molecular ship-in-a-bottle architecture remains a challenging one to make. Herein, we report a porphyrin-based suit[4]ane, which is composed of a porphyrin with four protruding ligands (two phenyl groups and two bromine atoms) called the limbs that are encompassed by a tricyclic octacationic cyclophane. The suit[4]ane can be obtained by slippage, a mechanism by which the cyclophane is able to open up two of its entrances in order to take up the porphyrin at high temperature and close them down at low temperature, locking the porphyrin inside its binding cavity. Dynamic 1H NMR spectroscopy reveals that the trapped porphyrin inside the cyclophane rocks back and forth in the suit[4]ane about 1000 times a second.