Tetraamido-oxacalix[4]arene Derivatives: Synthesis, Structures and Supramolecular Assemblies

Authors

  • Lingwei Kong,

    1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China
    Search for more papers by this author
  • Mingliang Ma,

    Corresponding author
    1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China
    • Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China, Tel.: 0086-021-20325166; Fax: 0086-021-20325173
    Search for more papers by this author
  • Xiaoli Zhao,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, and Department of Chemistry, East China Normal University, Shanghai 200062, China
    Search for more papers by this author
  • Yahua Liu,

    1. Medicinal Chemistry, ChemBridge Research Laboratories Inc., San Diego, CA 92127, USA
    Search for more papers by this author
  • Xianqiang Mi,

    1. Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
    Search for more papers by this author
  • Biao Jiang,

    Corresponding author
    1. Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
    • Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
    Search for more papers by this author
  • Ke Wen

    Corresponding author
    1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China
    2. Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
    • Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China, Tel.: 0086-021-20325166; Fax: 0086-021-20325173
    Search for more papers by this author

Abstract

Tetraamido-oxacalix[4]arene derivatives have been synthesized via the reactions of tetraamino-oxacalix[4]arene with excess butyryl chloride, octanoyl chloride, benzoyl chloride and p-toluenesulfonyl chloride, respectively. 1H NMR results suggest that these oxacalix[4]arene derivatives preferentially adopt the 1,3-alternate (saddle-like) conformation in solution, which were also the case in the solid state as demonstrated by single crystal X-ray analysis. A dimerized slipped capsule could be formed by tetra-butyramido-oxacalix[4]arene in the solid state via intermolecular hydrogen bond interactions under the assistance of two encapsulated methanol molecules. On the other hand, a molecular cavity was formed by tetra-p-toluenesulfonamido-oxacalix[4]arene which can encapsulate a solvent molecule of ethyl acetate.

Ancillary