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

Rudy J. Wojtecki, Qiong Wu, J. Casey Johnson, Dale G. Ray, Lashanda T J Korley, Stuart J. Rowan

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4440-4448
Number of pages9
JournalChemical Science
Volume4
Issue number12
DOIs
Publication statusPublished - 2013
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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