Rigid tetraarylene-bridged cavitands from reduced-symmetry resorcin[4]arene derivatives

Container molecules (cavitands) derived from resorcin[4]arene are of broad interest in supramolecular chemistry as hosts and fragments of larger constructs. Herein is presented a new class of rigid cavitand where the resorcin[4]arene carbon framework is extended with four bridging arylene rings. Two tenable, isomeric precursors of differing symmetry (C_2v and C₄) were prepared, of which only one afforded the desired fused bowl. X-ray crystallographic studies provide conformational insight, and show that the cavitand can bind small molecules in the solid state.