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Triptycene-Derived Oxacalixarenes as New Wheels for the Synthesis of [2]Rotaxanes: Acid–Base- and Metal-Ion-Switchable Complexation Processes

Authors

  • Shu-Zhen Hu,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China), Fax: (+86) 10-62554449
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  • Prof. Chuan-Feng Chen

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China), Fax: (+86) 10-62554449
    • Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China), Fax: (+86) 10-62554449
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Abstract

A pair of triptycene-derived oxacalixarenes, 1 a and 1 b, containing two naphthyridine subunits have been synthesized by a convenient one-pot approach. Macrocycles 1a and 1b are diastereomers, with 1a being a cis isomer with a boat-like 1,3-alternate conformation and 1b being a trans isomer with a curved boat-like conformation in the solid state. Both 1a and 1b have fixed conformations in solution at room temperature, as revealed by variable-temperature 1H NMR spectroscopy experiments. It was found that oxacalixarenes 1a and 1b could both form 1:1 [2]pseudorotaxane-type complexes with paraquat derivatives with different functional groups in solution and in the solid state, which resulted in the further synthesis of a pair of novel isomeric [2]rotaxanes. Moreover, the controlled dethreading and rethreading processes of the [2]pseudorotaxanes were also easily achieved by acid–base stimuli or Hg2+ association/dissociation.

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