Journal
DALTON TRANSACTIONS
Volume 44, Issue 12, Pages 5692-5702Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4dt03848g
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Funding
- National Natural Science Foundation of China [21271092, 21071069, 21171078]
- Science Foundation of Gansu Province of China [1308RJ2A121]
- project for National Basic Science Personnel Training Fund [J1103307]
- ScGrid of Supercomputing Center of Chinese Academy of Sciences
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Seven new type metallocavitand complexes 1-7 were synthesized via the self-assembly of aluminum and magnesium atrane-likes. The recognition of R-2-butanol from racemic 2-butanol can be achieved in the chiral cavity of metallocavitand complex 5. The crystal structure of complex 5 showed that the enantio-selectivity of the center cavity for the inclusion of two 2-butanol molecules is higher than that of the groups at the outer rim, which indicates that the size-limited cavity is more sensitive to the chirality of 2-butanol. Furthermore, desorption of R-2-butanol is successful through vacuumization which afforded complex 6 and gives R-2-butanol with an enantiomeric excess (ee) value of 53(+/- 1)%. The reaction of enantiopure H3L2, (MgBu2)-Bu-n, and racemic 1-phenylethanol afforded complex 7. The structure of complex 7 showed that the center cavity was occupied by three H2O molecules and one molecular R-1-phenylethanol suspended in the outer rim of the metallocavitand via a hydrogen bond, which indicated that 1-phenylethanol is too bulky for the size-limited cavity. Because a certain amount of racemic 1-phenylethanol is also co-crystallized in the unit cell, the final separated 1-phenylethanol has an ee value of 33(+/- 1)%. The host-guest mechanism for the separation is clearly determined through X-ray crystal structural analysis.
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