Issue 22, 2012
From the journal:

Chemical Communications

Induced preference for axial chirality in a triarylmethylium o,o-dimer upon complexation with natural γ-cyclodextrin: strong ECD signaling and fixation of supramolecular chirality to molecular chirality†

Takanori Suzuki,*a   Hitomi Tamaoki,a   Kazuhisa Wada,a   Ryo Katoono,a   Tatsuo Nehira,b   Hidetoshi Kawai‡a  and  Kenshu Fujiwaraa  

* Corresponding authors

a Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan
E-mail: tak@sci.hokudai.ac.jp
Fax: +81 11 706 2714
Tel: +81 11 706 2714

b Graduate School of Integrated Arts and Sciences, Hiroshima University, Higashi-hiroshima 739-8521, Japan

Abstract

The ratio of the easily interconverting rotational isomers of biphenyl-2,2′-diylbis[bis(4-dimethylaminophenyl)methylium] (R)/(S)-1a2+ can be biased to prefer an R configuration upon 1 : 1 complexation with γ-cyclodextrin in water. Through the reaction with Na2S, the preference of 1a2+@γ-CyD for an axial chirality of R can be fixed as the M-helicity of dihydrothiepin 2.

Graphical abstract: Induced preference for axial chirality in a triarylmethylium o,o-dimer upon complexation with natural γ-cyclodextrin: strong ECD signaling and fixation of supramolecular chirality to molecular chirality

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Article information

DOI
https://doi.org/10.1039/C2CC17475H
Article type
Communication
Submitted
30 Nov 2011
Accepted
17 Jan 2012
First published
18 Jan 2012

Chem. Commun., 2012,48, 2812-2814

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Induced preference for axial chirality in a triarylmethylium o,o-dimer upon complexation with natural γ-cyclodextrin: strong ECD signaling and fixation of supramolecular chirality to molecular chirality

T. Suzuki, H. Tamaoki, K. Wada, R. Katoono, T. Nehira, H. Kawai and K. Fujiwara, Chem. Commun., 2012, 48, 2812 DOI: 10.1039/C2CC17475H

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