Format

Send to

Choose Destination
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.

Author information

1
†Shanghai Advanced Research Institute, Chinese Academy of Science, Shanghai 201210, China.
2
‡University of Chinese Academy of Sciences, Beijing 100039, P. R. China.
3
§School of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, Sichuan, P. R. China.
4
∥Shanghai Key Laboratory of Green Chemistry and Chemical Processes and Department of Chemistry, East China Normal University, Shanghai 200062, China.
5
⊥Medicinal Chemistry, ChemBridge Research Laboratories, Inc., San Diego, California 92127, United States.
6
#School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China.

Abstract

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.

PMID:
26219027
DOI:
10.1021/acs.joc.5b01038
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center