Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 21, Pages 8094-8098Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201916285
Keywords
chirality inversion; electrochemistry; molecular universal joint; pillar[6]arene; supramolecular chemistry
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Funding
- National Natural Science Foundation of China [21871194, 21971169, 21572142]
- National Key Research and Development Program of China [2017YFA0505903]
- Science & Technology Department of Sichuan Province [2019YJ0160, 2019YJ0090, 2017SZ0021]
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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.
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