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Chiroptical molecular propellers based on hexakis(phenylethynyl)benzene through the complexation-induced intramolecular transmission of local point chirality†
Keiichi Kusaka,Shunsuke Kawai,Yuki Tanaka,Keisuke Hanada,Tatsuo Nehira,Kenshu Fujiwara,Takanori Suzuki
Organic & Biomolecular Chemistry Pub Date : 08/28/2014 00:00:00 , DOI:10.1039/C4OB01601G
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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