Issue 12, 2013

Optimizing the formation of 2,6-bis(N-alkyl-benzimidazolyl)pyridine-containing [3]catenates through component design

Abstract

The 2,6-bis(N-alkyl-benzimidazolyl)pyridine (Bip) ligand has been utilized to access mechanically interlocked [3]catenanes via metal-templating. Components containing the Bip ligand, namely macrocycles and linear threads, were designed to self-assemble upon the addition of transition metal ions into [3]metallopseudorotaxanes that require a single olefin metathesis reaction to yield the [3]catenate. Utilizing two-dimensional diffusion-ordered NMR spectroscopy (DOSY) the crude reaction mixture resulting from the ring-closing reaction of this template was studied. It was shown that the yield of the [3]catenates was dependent on the preorganization and conformational flexibility of the thread-like component and the size of the N-alkyl substituents on the Bip in the macrocyclic component. Through judicious design of both components the resulting reaction distribution can be altered to predominantly favour the formation of the [3]catenate. Furthermore, after de-metalation and purification the resulting [3]catenanes were fully characterized by a variety of NMR and mass spectroscopy techniques.

Graphical abstract: Optimizing the formation of 2,6-bis(N-alkyl-benzimidazolyl)pyridine-containing [3]catenates through component design

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Jul 2013
Accepted
10 Sep 2013
First published
20 Sep 2013

Chem. Sci., 2013,4, 4440-4448

Optimizing the formation of 2,6-bis(N-alkyl-benzimidazolyl)pyridine-containing [3]catenates through component design

R. J. Wojtecki, Q. Wu, J. C. Johnson, D. G. Ray, L. T. J. Korley and S. J. Rowan, Chem. Sci., 2013, 4, 4440 DOI: 10.1039/C3SC52082J

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