Consequences of Subtle Chiral Effects: From ‘Majority-Rules’ to ‘Minority-Rules’
Patrick J. M. Stals A B C , Müge Artar A B , Pim Vendrig A , Anja R. A. Palmans A B and E. W. Meijer A B D
+ Author Affiliations
- Author Affiliations
A Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, NL 5600 MB Eindhoven, The Netherlands.
B Institute for Complex Molecular Systems, Eindhoven University of Technology, PO Box 513, NL 5600 MB Eindhoven, The Netherlands.
C DSM Coating Resins, Sluisweg 12, 5145 PE Waalwijk, The Netherlands.
D Corresponding author. Email: e.w.meijer@tue.nl
Australian Journal of Chemistry 68(4) 622-626 https://doi.org/10.1071/CH14596
Submitted: 29 September 2014 Accepted: 22 October 2014 Published: 22 December 2014
Abstract
Mixing experiments were conducted on dilute solutions of asymmetrically substituted benzene-1,3,5-tricarboxamides (BTAs) with stereogenic methyl groups ranging from the α- to the δ-position with respect to the amide in one of the three side groups. While normally the majority compound determines the helical sense preference of the formed supramolecular polymers, we find here that several combinations show a helical preference governed by the minority compound. BTAs with the methyl substituent at the α- and γ-position overrule the helical preference of BTAs with the methyl substituent at the β- and δ-position. This new effect is referred to as a ‘minority-rules’ system.
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