Issue 6, 2015

Molecular recognition of upper rim functionalized cavitand and its unique dimeric capsule in the solid state

Abstract

Cavitand 1 possesses four 2,2′-bipyridyl pillars on its upper rim that encapsulates small guests, such as nitromethane, acetonitrile, methyl acetate, ethyl acetate, and N-methylacetamide, into a deep cavity to form host–guest complexes in a 1 : 1 ratio. Nitroethane, N,N-dimethylformamide, and N,N-dimethylacetamide were not bound in this manner. A guest-binding study and molecular mechanics calculations revealed that the four 2,2′-bipyridyl pillars of cavitand 1 created a steric boundary that is responsible for selective guest recognition. In the solid state, cavitand 2 formed a unique chiral capsule 22 by π–π stacking interactions between the 2,2′-bipyridyl pillars. A nitromethane molecule was unusually placed deep inside the cavity, as directed by the multiple hydrogen bonding interactions between the nitromethane oxygen atoms, the C–H bonds of the bridge methylenes and the pillar phenyl groups.

Graphical abstract: Molecular recognition of upper rim functionalized cavitand and its unique dimeric capsule in the solid state

Supplementary files

Article information

Article type
Paper
Submitted
22 Oct 2014
Accepted
19 Nov 2014
First published
21 Nov 2014

Org. Biomol. Chem., 2015,13, 1647-1653

Molecular recognition of upper rim functionalized cavitand and its unique dimeric capsule in the solid state

M. Kobayashi, M. Takatsuka, R. Sekiya and T. Haino, Org. Biomol. Chem., 2015, 13, 1647 DOI: 10.1039/C4OB02251C

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