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Formation of copper(I)-templated [2]rotaxanes using “click” methodology: influence of the base, the thread and the catalyst

  • Fabien Durola
  • Stéphanie Durot
  • Valérie Heitz
  • Antoine Joosten
  • Jean-Pierre Sauvage
  • Yann Trolez
Original Article

Abstract

Three new copper(I)-assembled [2]rotaxanes incorporating the same macrocycle and different axes containing a bipy, a phen or a terpy have been synthesized thanks to CuAAC reaction for attaching the stoppers. The influence of the nature of the base used for the stoppering reaction was investigated on the formation of the bipy-containing rotaxane. The yield of the [2]rotaxane synthesis was increased when using a phen as a coordinating unit in the thread with [Cu(CH3CN)4](PF6) as catalyst. The strong influence of the nature of the catalyst was clearly evidenced for the formation of the terpy rotaxane, increasing the yield of the stoppering reaction from 0 to 95% by just substituting the Cu(I) catalyst. Finally, the best conditions found for our systems are the use of Na2CO3 as a base and Cu(tren′)Br as a catalyst.

Keywords

Rotaxane Copper(I) Click chemistry Phenanthroline Bipyridine Terpyridine 

Notes

Acknowledgments

We thank the Agence Nationale de la Recherche (ANR no. 07-Blan-0174, MOLPress) for its financial support as well as the French Ministry of Research for a fellowship to YT.

Supplementary material

10847_2011_9986_MOESM1_ESM.doc (174 kb)
Supplementary material 1 (DOC 174 kb)

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Copyright information

© Springer Science+Business Media B.V. 2011

Authors and Affiliations

  • Fabien Durola
    • 1
  • Stéphanie Durot
    • 1
  • Valérie Heitz
    • 1
  • Antoine Joosten
    • 1
  • Jean-Pierre Sauvage
    • 1
  • Yann Trolez
    • 1
  1. 1.Laboratoire de Chimie Organo-MinéraleInstitut de Chimie de Strasbourg, UMR 7177 CNRS, Université de StrasbourgStrasbourg CedexFrance

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