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An efficient [3]catenane formation in a dynamic combinatorial library
Jianwei Li and Sijbren Otto
University of Groningen, Centre for System Chemistry, Stratingh Institute, Nijenborgh 4, 9747 AG
Groningen, The Netherlands
E-mail: Jianwei.li@rug.nl
Catenanes, consisting of two or more interlocked macrocyclic rings, often exhibit
markedly novel properties 1 . Although there are several strategies to synthesize this kind
of molecules, synthetic challenges still remain 1 . Dynamic combinatorial chemistry is a
useful tool to explore synthetic receptors and ligands for biomolecules 2 . Dynamic
combinatorial libraries (DCLs) are produced by linking building blocks together using a
reversible reaction, resulting in a thermodynamically controlled product distribution.
Addition of a guest or a biomolecule shifts the distribution to those library members that
bind best to the external target; a process referred to as templating. Considering the
interaction between cyclodextrin homologues and azobenzene derivatives is strong, we
set up a library using β-cyclodextrin and a dithiol-azobenzene derivative. We have
found that two molecules of β-cyclodextrin were interlocked on one disulfide bonds
linking tetramer macrocycle. The yield of the [3]catenane formation is 95%. This
efficient synthesis of catenane by is proved by HPLC/MS and 1
H NMR. These results
provide a new strategy for synthesizing catenane.
1. O. S. Miljanic, J. R. Heath and J. F. Stoddart, J. Am. Chem. Soc., 2007, 129, 8236-8246.
2. (a) P. T. Corbett, J. Leclaire, L. Vial, K. R. West, J. L. Wietor, J. K. M. Sanders and S. Otto, Chem.
Rev. 2006, 106, 3652-3711. (b) R. A. R. Hunt and S. Otto, Chem. Commun. 2011, 47, 847-858.