Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 35, Pages 12170-12174Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201907040
Keywords
crystal engineering; hydrogen bonds; macrocycles; nanotubes; supramolecular chemistry
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Funding
- JST ERATO [JPMJER1301]
- KAKENHI [17H01033, 19H05376, 19H02552]
- Grants-in-Aid for Scientific Research [19H05376, 19H02552, 17H01033] Funding Source: KAKEN
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Upon encapsulating an oval-shaped hydrocarbon guest, a cylindrical host deforms its shape to maximize intermolecular contacts. Structure-assembly relationship studies with a series of hydrocarbon guests disclosed the importance of molecular shapes and CH-pi contacts. Multiple contacts and weak CH-pi hydrogen bonds resulted in an optimal assembly; however, the shape deformation resulted in severe retardation of rotational motions in the crystal. Thus, unlike a circular guest, the oval-shaped guest did not change its orientation in the host. Unexpectedly, the planar guest did not affect the packing structure to form a double helix in intertwined host arrays.
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