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Updated: May 29, 2025

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Published on: February 7, 2017
Chiroptical Properties of Chiral Macrocycles Composed of Axially Chiral Binaphthyl and Bithiophene
Hikari Kawashima1, Daiki Tauchi1, Misa Sakura2
1Department of Chemistry, Graduate School of Science, Kitasato University, 1-15-1 Kitasato Minami-ku, Sagamihara, Kanagawa, 252-0373, Japan.
Abstract:
Stereogenic macrocycles composed of axially chiral binaphthyls and bithiophenes were synthesized. The bis(1,5-cyclooctadiene)nickel(0)-catalyzed coupling of an enantiomeric precursor yielded a cyclic dimer and trimer with doubly-twisted and triply-twisted triangular geometries, respectively. The orientation of the bithiophenes, s-cis, and s-trans in the cyclic compounds significantly altered their macrocyclic structure. Mixing of conformers in the cyclic dimer results in complex chiroptical properties, leading to bisignate-type spectra, which are rarely observed in circularly polarized luminescence.
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