Reversible encapsulation and release of fullerenes using calix[n]phenoxazines

This investigation presents the synthesis of butyl-decorated calix[n]phenoxazines of varying sizes by kinetic control and the ring-expansion of calix[3]phenoxazine, which uniquely exhibits distinct binding affinities for fullerenes C₆₀ and C₇₀. Calix[3]phenoxazine demonstrates a higher binding affinity for cationic ammonium, which can be reversibly deprotonated and protonated, enabling the reversible release and reloading of fullerenes. This system holds potential for applications in fullerene extraction and separation.