Geminiarene: Molecular Scale Dual Selectivity for Chlorobenzene and Chlorocyclohexane Fractionation

In
this work, a new version of macrocyclic arenes, namely geminiarene,
has been designed and synthesized for guest complexation and chlorobenzene/chlorocyclohexane
mixture separation with excellent dual selectivity. Due to its unique
dual/gemini conformational feature, not only chlorocyclohexane can
be separated from chlorobenzene with exceeding 97% purity but also
chlorobenzene can be separated from chlorocyclohexane with purity
over 88%, and the dual selective fractionation process could be achieved
in only one cycle of operation. Significantly, we demonstrate that
the dual selectivity capability is essentially a competition of the
stability between the guest-free and guest-loaded crystalline phases
of geminiarene. We strongly believe that this work and the idea of
multiple selective separation systems will open up new perspectives
on macrocycle-based solid-state host–guest chemistry and molecular
scale separation materials.