Megalo-Cavitands: Synthesis of Acridane[4]arenes and Formation of Large, Deep Cavitands for Selective C70 Uptake

Deep cavitands, concave molecular containers, represent an important supramolecular host class that has been explored for a variety of applications ranging from sensing, switching, purification and adsorption to catalysis. A major limitation in the field has been the cavitand volume that is restricted by the size of the structural platform utilized (diameter approx. 7 angstrom). We here report the synthesis of a novel, unprecedentedly large structural platform, named acridane[4]arene (diameter approx. 14 angstrom), suitable for the construction of cavitands with volumes of up to 814 angstrom(3). These megalo-cavitands serve as size-selective hosts for fullerenes with mM to sub-mu M binding affinity for C-60 and C-70. Furthermore, the selective binding of fullerene C-70 in the presence of C-60 was demonstrated.

Automated summary

This study reports the synthesis of a novel structural platform suitable for constructing megalo-cavitands with large volumes. These megalo-cavitands selectively bind to C-60 and C-70.