Homochiral [2]Catenane and Bis[2]catenane from Alleno-Acetylenic Helicates - A Highly Selective Narcissistic Self-Sorting Process

Homochiral strands of alternating alleno-acetylenes and phenanthroline ligands (P)-1 and (P 2)-2, as well as their corresponding enantiomers, selectively assemble with the addition of silver­(I) salt to yield dinuclear and trinuclear double helicates, respectively. Upon increasing the solvent polari...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-10, Vol.137 (39), p.12502-12505
Main Authors: Gidron, Ori, Jirásek, Michael, Trapp, Nils, Ebert, Marc-Olivier, Zhang, Xiangyang, Diederich, François
Format: Article
Language:English
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Summary:Homochiral strands of alternating alleno-acetylenes and phenanthroline ligands (P)-1 and (P 2)-2, as well as their corresponding enantiomers, selectively assemble with the addition of silver­(I) salt to yield dinuclear and trinuclear double helicates, respectively. Upon increasing the solvent polarity, the dinuclear and trinuclear helicates interlock to form a [2]­catenane and bis[2]­catenane, bearing 14 chirality elements, respectively. The solid-state structure of the [2]­catenane reveals a nearly perfect fit of the interlocked strands, and the ECD spectra show a significant amplification of the chiroptical properties upon catenation, indicating stabilization of the helical secondary structure. Highly selective narcissistic self-sorting was demonstrated for a racemic mixture consisting of both short and long alleno-acetylenic strands, highlighting their potential for the preparation of linear catenanes of higher order.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b08649