Dihalobenzene Shape Sorting by Nonporous Adaptive Crystals of Perbromoethylated Pillararenes

The separation of dihalobenzene isomers, such as dichlorobenzene isomers and difluorobenzene isomers, has a high practical value in both synthetic chemistry and industrial production. Herein we provide a simple to operate and energy‐efficient adsorptive separation method using nonporous adaptive cry...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-03, Vol.58 (12), p.3981-3985
Main Authors: Li, Errui, Zhou, Yujuan, Zhao, Run, Jie, Kecheng, Huang, Feihe
Format: Article
Language:English
Subjects:
Adsorptivity
Crystal structure
Crystals
Dichlorobenzene
host–guest systems
Industrial production
Isomers
molecular separation
nonporous adaptive crystals
Organic chemistry
pillararenes
Selectivity
Separation
supramolecular chemistry
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Summary:The separation of dihalobenzene isomers, such as dichlorobenzene isomers and difluorobenzene isomers, has a high practical value in both synthetic chemistry and industrial production. Herein we provide a simple to operate and energy‐efficient adsorptive separation method using nonporous adaptive crystals of perbromoethylated pillar[5]arene (BrP5) and pillar[6]arene (BrP6). BrP6 crystals show a preference towards the ortho isomer of dichlorobenzene in isomer mixtures, but cannot discriminate difluorobenzene isomers. Single‐crystal structures reveal that this selectivity is derived from the stability of the new host–guest crystal structure of BrP6 after uptake of the preferred guest and the binding strength of the host–guest interactions. Furthermore, because of the reversible transition between guest‐free and guest‐loaded structures, BrP6 crystals are recyclable. Separate ways: A simple and energy‐efficient separation of dihalobenzenes is made possible by using nonporous perbromoethylated pillar[6]arene (BrP6) crystals. BrP6 crystals show a preference towards the ortho isomer of dichlorobenzene but cannot discriminate difluorobenzene isomers.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201900140