Issue 10, 2009
From the journal:

New Journal of Chemistry

[3]Rotaxanes and [3]pseudorotaxanes with a rigid two-bidentate chelate axle threaded through two coordinating rings†

Jean-Paul Collin,a   Jean-Pierre Sauvage,*a   Yann Troleza  and  Kari Rissanen‡b  

* Corresponding authors

a Laboratoire de Chimie Organo-Minérale, Institut de Chimie, LC3 UMR 7177 du CNRS, Université de Strasbourg, 4 rue Blaise Pascal, France
E-mail: sauvage@chimie.u-strasbg.fr
Fax: +33 (0)3 90 24 13 68

b Nanoscience Center, Department of Chemistry, University of Jyväskylä, P.O. Box 35, Finland
E-mail: kari.t.rissanen@jyu.fi

Abstract

New [3]rotaxanes and [3]pseudorotaxanes have been synthesised using the “gathering and threading” effect of copper(I). By using click chemistry as the “stoppering” reaction, a good yield of the [3]rotaxane was obtained, either as a dicopper complex or as a metal-free compound after demetallation. The axle contains a central rigid aromatic block incorporating two bidentate chelates, and the threaded macrocycles are 30-membered rings. A model dicopper(I) [3]pseudorotaxane whose axle was end-functionalised by triisopropylsilyl groups could be crystallised and studied by X-ray diffraction. A particularly attractive structure was obtained showing a “slanted” geometry for the two rings and the axle, the two 1,10-phenanthroline units of the rings being almost parallel to one another but their respective mean planes being more than 7 Å apart.

Graphical abstract: [3]Rotaxanes and [3]pseudorotaxanes with a rigid two-bidentate chelate axle threaded through two coordinating rings

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Article information

DOI
https://doi.org/10.1039/B9NJ00278B
Article type
Paper
Submitted
22 Jun 2009
Accepted
23 Jul 2009
First published
19 Aug 2009

New J. Chem., 2009,33, 2148-2154

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[3]Rotaxanes and [3]pseudorotaxanes with a rigid two-bidentate chelate axle threaded through two coordinating rings

J. Collin, J. Sauvage, Y. Trolez and K. Rissanen, New J. Chem., 2009, 33, 2148 DOI: 10.1039/B9NJ00278B

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