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Updated: Jun 14, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
One-pot enantioselective extraction of chiral fullerene C76 using a cyclic host carrying an asymmetrically distorted,
Yoshiaki Shoji1, Kentaro Tashiro, Takuzo Aida
1Department of Chemistry and Biotechnology, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.
Abstract:
Optical resolution of nonsubstituted chiral fullerenes such as C(76) is one of the most challenging subjects in host-guest chemistry. The novel cyclic host 1(2H), which bears a meso-diaryl-beta-octaethylporphyrin (P(2H)) unit on one side and its chiral N-2-acetoxyethyl derivative (P(N-EtOAc)) on the other, traps C(76) enantioselectively in its cavity and furnishes 7% enantiomeric excess in a single extraction. Control experiments using reference hosts indicated the importance of the high pi-basicity and large asymmetric distortion of the chiral N-substituted porphyrin unit (P(N-EtOAc)) in 1(2H) for the enantioselection of C(76).
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