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Controlled Dynamic Helicity of a Folded Macrocycle Based on a Bisterephthalamide with a Twofold Z‐Shaped Structure
Author(s) -
Katoono Ryo,
Kusaka Keiichi,
Fujiwara Kenshu,
Suzuki Takanori
Publication year - 2014
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.201402658
Subject(s) - helicity , folding (dsp implementation) , chirality (physics) , crystallography , supramolecular chemistry , unit (ring theory) , chemistry , stereochemistry , physics , crystal structure , mathematics , engineering , chiral symmetry breaking , mathematics education , particle physics , quantum mechanics , quark , nambu–jona lasinio model , electrical engineering
Dynamic helicity in a folded macrocycle and control of the helical preference are described. We designed macrocycle 1 with a dual mode of folding through the integration of two flexible units that are arranged twice to form a cyclic structure. As a folding unit, we used a terephthalamide skeleton and a Z‐shaped hydrocarbon: the former acted as a control unit to induce a preference of a particular sense of dynamic helicity and the latter was just a spacer. A terephthalamide unit provided a binding site for capturing a ditopic hydrogen‐bonding guest when it adopted helically folded syn forms ( M / P ). Thus, only the terephthalamide unit controlled the helical sense of dynamic helicity in a folded macrocycle through the supramolecular transmission of chirality upon complexation with a chiral ditopic guest. In addition, chirality on a host could also contribute to the control of the helical preference in a folded macrocycle, which led to exceptionally enhanced chiroptical signals.