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Atropisomerism in a Belt‐Persistent Nanohoop Molecule: Rotational Restriction Forced by Macrocyclic Ring Strain
Author(s) -
Hitosugi Shunpei,
Nakanishi Waka,
Isobe Hiroyuki
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200187
Subject(s) - atropisomer , ring (chemistry) , strain (injury) , chemistry , steric effects , stereochemistry , arylene , molecule , rotation (mathematics) , crystallography , computer science , artificial intelligence , biology , organic chemistry , alkyl , anatomy , aryl
Enough strain! Strain in a macrocyclic ring hinders the rotation of an arylene panel in a nanohoop molecule containing four chrysenylene units (see picture). Unlike conventional rotational restrictions in biaryl systems, the new atropisomerism does not require any steric hinderance from the substituents. The study of atropisomerism also provides the first experimental insights into the relative stability of nanohoop structures.