Host-Enhanced Phenyl-Perfluorophenyl Polar-pi Interactions.

Phenyl-perfluorophenyl polar-pi interactions have been revisited for the design and fabrication of functional supramolecular systems. The relatively weak associative interactions (DeltaG approximately -1.0 kcal/mol) have limited their use in aqueous self-assembly to date. Herein, we propose a strategy to strengthen phenyl-perfluorophenyl polar-pi interactions by encapsulation within a synthetic host, thus increasing the binding affinity to DeltaG approximately -15.5 kcal/mol upon formation of heteroternary complexes through social self-sorting. These heteroternary complexes were used as dynamic, yet strong, cross-linkers in the fabrication of supramolecular gels, which exhibited excellent viscoelasticity, stretchability, self-recovery, self-healing as well as energy dissipation. This work unveils a general approach to exploit host-enhanced polar-pi interactions in the design of robust aqueous supramolecular systems.