Near-Ideal Xylene Selectivity in Adaptive Molecular Pillar[ n]arene Crystals

Journal of the American Chemical Society
Kecheng JieAndrew I Cooper

Abstract

The energy-efficient separation of alkylaromatic compounds is a major industrial sustainability challenge. The use of selectively porous extended frameworks, such as zeolites or metal-organic frameworks, is one solution to this problem. Here, we studied a flexible molecular material, perethylated pillar[ n]arene crystals ( n = 5, 6), which can be used to separate C8 alkylaromatic compounds. Pillar[6]arene is shown to separate para-xylene from its structural isomers, meta-xylene and ortho-xylene, with 90% specificity in the solid state. Selectivity is an intrinsic property of the pillar[6]arene host, with the flexible pillar[6]arene cavities adapting during adsorption thus enabling preferential adsorption of para-xylene in the solid state. The flexibility of pillar[6]arene as a solid sorbent is rationalized using molecular conformer searches and crystal structure prediction (CSP) combined with comprehensive characterization by X-ray diffraction and 13C solid-state NMR spectroscopy. The CSP study, which takes into account the structural variability of pillar[6]arene, breaks new ground in its own right and showcases the feasibility of applying CSP methods to understand and ultimately to predict the behavior of soft, adaptive molec...Continue Reading

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Citations

Nov 13, 2018·Chemical Communications : Chem Comm·Hui LiWei Tian
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Methods Mentioned

BETA
NMR
X-ray
differential scanning calorimetry

Software Mentioned

Global Lattice Energy Explorer
INADEQUATE
Gaussian09
BIOVIA
Gaussian
CHLEPG
Materials Studio
MacroModel
DMACRYS
COMPACK

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