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Efficient Separation of cis ‐ and trans ‐1,2‐Dichloroethene Isomers by Adaptive Biphen[3]arene Crystals
Author(s) -
Wang Yiliang,
Xu Kaidi,
Li Bin,
Cui Lei,
Li Jian,
Jia Xueshun,
Zhao Hongbin,
Fang Jianhui,
Li Chunju
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201905563
Subject(s) - selectivity , sorption , chemistry , adsorption , cis–trans isomerism , solvent , crystallography , yield (engineering) , structural isomer , pentamer , topology (electrical circuits) , materials science , stereochemistry , organic chemistry , catalysis , biochemistry , mathematics , combinatorics , metallurgy
Reported here is the highly efficient separation of industrially important cis ‐ and trans ‐1,2‐dichloroethene ( cis ‐DCE and trans ‐DCE) isomers by activated crystalline 2,2′,4,4′‐tetramethoxyl biphen[3]arene (MeBP3) materials, MeBP3α. MeBP3 can be synthesized in excellent yield (99 %), and a cyclic pentamer is also obtained when using 1,2‐dichloroethane as the solvent. The structure of MeBP3 in the CH 3 CN@MeBP3 crystal displays a triangle‐shape topology, forming 1D channels through window‐to‐window packing. Desolvated crystalline MeBP3 materials, MeBP3α, preferentially adsorb cis ‐DCE vapors over its trans isomer. MeBP3α is able to separate cis ‐DCE from a 50:50 (v/v) cis / trans ‐isomer mixture, yielding cis ‐DCE with a purity of 96.4 % in a single adsorption cycle. Single‐crystal structures and powder X‐ray diffraction patterns indicate that the uptake of cis ‐DCE triggers a solid‐state structural transformation of MeBP3, suggesting the adaptivity of MeBP3α materials during the sorption process. Moreover, the separation can be performed over multiple cycles without loss of separation selectivity and capacity.