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J Org Chem. 2015 Aug 21;80(16):7994-8000. doi: 10.1021/acs.joc.5b01038. Epub 2015 Aug 7.

Selectivity and Cooperativity in the Binding of Multiple Guests to a Pillar[5]arene-Crown Ether Fused Tricyclic Host.

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†Shanghai Advanced Research Institute, Chinese Academy of Science, Shanghai 201210, China.
‡University of Chinese Academy of Sciences, Beijing 100039, P. R. China.
§School of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, Sichuan, P. R. China.
∥Shanghai Key Laboratory of Green Chemistry and Chemical Processes and Department of Chemistry, East China Normal University, Shanghai 200062, China.
⊥Medicinal Chemistry, ChemBridge Research Laboratories, Inc., San Diego, California 92127, United States.
#School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China.


A novel tricylic host molecule 1 that consists of two pillar[5]arene units and a crown ether ring was found to selectively bind two kinds of guest molecules with different shapes, sizes, and electronic constitutions, namely 1,4-dicyanobutane G1 and paraquat G2, with its two macrocyclic subunits, to form a four-component complex 2G1⊂1⊃G2. An (1)H NMR study of stepwise bindings of G1 and G2 to host 1 in CDCl3/DMSO-d6 revealed that the strength of the association between complex 2G1⊂1 and guest G2 was only one-fourth of that between free 1 and G2, demonstrating a negative heterotropic cooperativity of G1 in the binding of G2 to host 1.

[Indexed for MEDLINE]

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