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Retarded Solid‐State Rotations of an Oval‐Shaped Guest in a Deformed Cylinder with CH–π Arrays
Author(s) -
Matsuno Taisuke,
Fukunaga Kengo,
Sato Sota,
Isobe Hiroyuki
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201907040
Subject(s) - planar , intermolecular force , cylinder , crystallography , hydrogen bond , close packing of equal spheres , deformation (meteorology) , materials science , hydrocarbon , solid state , chemical physics , crystal structure , orientation (vector space) , helix (gastropod) , chemistry , geometry , molecule , composite material , geology , paleontology , computer graphics (images) , mathematics , organic chemistry , snail , computer science
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–π contacts. Multiple contacts and weak CH–π 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.