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Issue 47, 2014
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Chiroptical molecular propellers based on hexakis(phenylethynyl)benzene through the complexation-induced intramolecular transmission of local point chirality

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Abstract

We designed hexakis(phenylethynyl)benzene derivatives with a tertiary amide group on each blade to achieve a helically biased propeller arrangement through the complexation-induced intramolecular transmission of point chirality. A hydrogen-bonding ditopic guest was captured at two amide groups, and thus could pair two neighboring blades to form a supramolecular cyclic structure, in which an auxiliary chiral group associated with a blade acted as a chiral handle to control the helical bias, while the chiral auxiliary did not exert any helical influence on the dynamic helicity in the absence of a guest due to the high flexibility of each blade.

Graphical abstract: Chiroptical molecular propellers based on hexakis(phenylethynyl)benzene through the complexation-induced intramolecular transmission of local point chirality

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Publication details

The article was received on 28 Jul 2014, accepted on 28 Aug 2014 and first published on 28 Aug 2014


Article type: Paper
DOI: 10.1039/C4OB01601G
Citation: Org. Biomol. Chem., 2014,12, 9532-9538
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    Chiroptical molecular propellers based on hexakis(phenylethynyl)benzene through the complexation-induced intramolecular transmission of local point chirality

    R. Katoono, K. Kusaka, S. Kawai, Y. Tanaka, K. Hanada, T. Nehira, K. Fujiwara and T. Suzuki, Org. Biomol. Chem., 2014, 12, 9532
    DOI: 10.1039/C4OB01601G

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