Tetraamido-oxacalix[4]arene Derivatives: Synthesis, Structures and Supramolecular Assemblies
Lingwei Kong
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China
Search for more papers by this authorCorresponding Author
Mingliang Ma
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China
Mingliang Ma, 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
Biao Jiang, Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
Ke Wen, 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 authorXiaoli Zhao
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 authorYahua Liu
Medicinal Chemistry, ChemBridge Research Laboratories Inc., San Diego, CA 92127, USA
Search for more papers by this authorXianqiang Mi
Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
Search for more papers by this authorCorresponding Author
Biao Jiang
Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
Mingliang Ma, 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
Biao Jiang, Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
Ke Wen, 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 authorCorresponding Author
Ke Wen
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China
Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
Mingliang Ma, 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
Biao Jiang, Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
Ke Wen, 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 authorLingwei Kong
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China
Search for more papers by this authorCorresponding Author
Mingliang Ma
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China
Mingliang Ma, 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
Biao Jiang, Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
Ke Wen, 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 authorXiaoli Zhao
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 authorYahua Liu
Medicinal Chemistry, ChemBridge Research Laboratories Inc., San Diego, CA 92127, USA
Search for more papers by this authorXianqiang Mi
Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
Search for more papers by this authorCorresponding Author
Biao Jiang
Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
Mingliang Ma, 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
Biao Jiang, Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
Ke Wen, 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 authorCorresponding Author
Ke Wen
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China
Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
Mingliang Ma, 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
Biao Jiang, Sustainable Technology Research Center, Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201203, China
Ke Wen, 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 authorAbstract
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.
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