Highly Selective Separation of Isopropylbenzene and α-Methylstyrene by Nonporous Adaptive Crystals of Perbromoethylated Pillararene via Vapor- and Liquid-Phase Adsorptions

Isopropylbenzene (IPB) and a-methylstyrene (AMS), two members of C9 aromatics, are important in both industrial production and laboratory research, but the separation of IPB/AMS mixtures is still a big challenge. Here, we provide a new strategy to separate IPB and AMS using nonporous adaptive crystals of four pillararenes, perethylated pillar[5]arene, perethylated pillar[6]arene, perbromoethylated pillar[5]arene, and perbromoethylated pillar[6]arene (BrP6). Among them, BrP6 selectively adsorbs IPB from an equal volume mixture of IPB and AMS with >95% purity for solid-vapor phase adsorption and >94% purity for solid-liquid phase adsorption, while the selectivities for the other three pillararenes are unsatisfactory. Single-crystal structural analyses combined with powder X-ray diffraction and differential scanning calorimetry experiments demonstrate that the selectivity arises from the different stabilities of guest-loaded BrP6 crystals. Moreover, the reversible transitions between guest-free and IPB-loaded structures indicate the preeminent recycling performance of BrP6 crystals.

Automated summary

The separation of IPB and AMS using nonporous adaptive crystals of four pillararenes, particularly BrP6, is effective and demonstrates excellent recycling performance. BrP6 shows high selectivity for adsorbing IPB and has reversible transitions between guest-free and IPB-loaded structures, making it a promising material for separation applications.