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Short Paper | Regular issue | Vol 94, No. 6, 2017, pp.1123-1132
Published online, 8th May, 2017
DOI: 10.3987/COM-17-13674
Stereoselective Encapsulation for a Triarylmethylium o,o-Dimer by Natural γ-Cyclodextrin: Origin of Chiral Recognition for the Axially Chiral Dicationic Guest

Takanori Suzuki,* José P. Cerón-Carrasco, Hitomi Tamaoki, Yusuke Ishigaki, Ryo Katoono, Takanori Fukushima, and Horacio Pérez-Sánchez*

*Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan

Abstract

Upon 1:1 complexation with γ-cyclodextrin (CyD) in water, easily interconverting rotational isomers of biphenyl-2,2'-diylbis[bis(4- dimethylaminophenyl)methylium] (R)/(S)-1a2+ were biased to prefer an R configuration (75 : 25 at 25 ºC). Docking and quantum chemical calculations revealed two modes (on-top and botton-side) of encapsulation of γ-CyD, which shed a light on the origin of the first chiral recognition of axially chiral dicationic dyes by using natural CyDs.