Elsevier

Tetrahedron Letters

Volume 50, Issue 10, 11 March 2009, Pages 1146-1150
Tetrahedron Letters

Synthesis of linked symmetrical [3] and [5]rotaxanes having an oligomeric phenylene ethynylene (OPE) core skeleton as a π-conjugated guest via double intramolecular self-inclusion

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Abstract

Linked symmetrical [3] and [5]rotaxanes consisting of an oligomeric phenylene ethynylene (OPE) framework as a π-conjugated guest moiety and lipophilic permethylated α-cyclodextrins (PM α-CDs), as macrocyclic hosts have been prepared by double intramolecular self-inclusion of an OPE guest unit carrying two PM α-CDs followed by capping with bulky stopper groups using click azide–alkyne Huisgen cycloaddition or Sonogashira coupling. The structures of these linked rotaxanes were determined by MALDI-TOF mass spectrum and two-dimensional NMR spectroscopy.

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Acknowledgments

The authors thank instrumental Analysis Center, Faculty of Engineering, Osaka University, for 2D NMR experiments. One of the authors S.T. express his special thanks for The Global coe (center of excellence) Program ‘Global Education and Research Center for Bio-Environmental Chemistry’ of Osaka University.

References and notes (13)

  • Tsuda, S.; Terao, J.; Tsurui, K.; Kambe, N., in...
  • P. Wautelet et al.

    Macromolecules

    (1996)
    S.P. Mcllroy et al.

    J. Org. Chem.

    (2005)
    Y. Zhao et al.

    Chem. Eur. J.

    (2005)
    S.W. Robey et al.

    J. Phys. Chem. C

    (2007)
    O. Mongin et al.

    Chem. Eur. J.

    (2007)
  • W. Holzer et al.

    Opt. Commun.

    (1999)
    J.M. Hong et al.

    Synth. Met.

    (1999)
    N.G. Pschirer et al.

    Chem. Commun.

    (2000)
    C. Huber et al.

    J. Am. Chem. Soc.

    (2001)
    W. Chen et al.

    J. Phys. Chem. B

    (2003)
    A.P.-Z. Clark et al.

    Nano Lett.

    (2005)
    Y.-G. Zhi et al.

    Eur. J. Org. Chem.

    (2006)
    C. Ding et al.

    Synlett

    (2007)
    A. Satrijo et al.

    Macromolecules

    (2007)
    X. Zhao et al.

    Macromolecules

    (2008)
    K. Kokado et al.

    J. Poly. Sci. Part A: Poly. Chem.

    (2008)
  • M. Hirohata et al.

    Synth. Met.

    (1997)
    A. Montali et al.

    Synth. Met.

    (1998)
    E. Arias-Marin et al.

    Langmuir

    (2000)
    S. Anderson

    Chem. Eur. J.

    (2001)
    S. Lu et al.

    Synth. Met.

    (2004)
    C.A. Breen et al.

    Nano Lett.

    (2005)
    L. Fenenko et al.

    Chem. Commun.

    (2007)
  • M.J. Frampton et al.

    Angew. Chem., Int. Ed.

    (2007)
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