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 and C) 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.