One-pot enantioselective extraction of chiral fullerene C76 using a cyclic host carrying an asymmetrically distorted, highly pi-basic porphyrin module.
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).
Shoji
Yoshiaki
Y
Department of Chemistry and Biotechnology, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.
Tashiro
Kentaro
K
Aida
Takuzo
T