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Redox‐Triggered Chirality Switching and Guest‐Capture/Release with a Pillar[6]arene‐Based Molecular Universal Joint
Author(s) -
Xiao Chao,
Wu Wanhua,
Liang Wenting,
Zhou Dayang,
Kanagaraj Kuppusamy,
Cheng Guo,
Su Dan,
Zhong Zhihui,
Chruma Jason J.,
Yang Cheng
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201916285
Subject(s) - chirality (physics) , moiety , enantiopure drug , chemistry , ferrocene , molecular switch , conformational change , circular dichroism , redox , supramolecular chemistry , molecule , self assembly , crystallography , stereochemistry , photochemistry , electrochemistry , crystal structure , enantioselective synthesis , electrode , organic chemistry , catalysis , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
A chiral electrochemically responsive molecular universal joint (EMUJ) was synthesized by fusing a macrocyclic pillar[6]arene (P[6]) to a ferrocene‐based side ring. A single crystal of an enantiopure EMUJ was successfully obtained, which allowed, for the first time, the definitive correlation between the absolute configuration and the circular dichroism spectrum of a P[6] derivative to be determined. The self‐inclusion and self‐exclusion conformational change of the EMUJ led to a chiroptical inversion of the P[6] moiety, which could be manipulated by both solvents and changes in temperature. The EMUJ also displayed a unique redox‐triggered reversible in/out conformational switching, corresponding to an occupation/voidance switching of the P[6] cavity, respectively. This phenomenon is an unprecedented electrochemical manipulation of the capture and release of guest molecules by supramolecular hosts.