Nondegenerate π-donor/π-acceptor [2]catenanes containing proton-ionizable 1H-1,2,4-triazole subunits: Synthesis and spontaneous resolution

Ermitas Alcalde, Lluïsa Pérez-García*, Susana Ramos, J. Fraser Stoddart, Andrew J P White, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Scopus citations


Chirality can hold the key to inducing directionality of motion in components of molecular devices. With this idea in mind, we describe here 1) the template-directed synthesis of two [2]catenanes wherein cyclobis(paraquat-p- phenylene) is interlocked with polyether macrocycles containing, in addition to one 3,5-bis(oxymethylene)-1H-1,2,4-triazole unit, either one 1,4-dioxybenzene or one 1,5-dioxynaphthalene ring system. We also report 2) the full characterization of both [2]catenanes by fast atom bombardment mass spectrometry (FABMS), X-ray crystallography, and dynamic 1H NMR spectroscopy. We reveal 3) the fact that the [2]catenanes not only exist, both in the solution-state and in the solid-state, as strictly one of the two possible translational isomers, but that they also exhibit spontaneous resolution on crystallization leading to formation of homochiral crystals, as indicated by X-ray crystallography and circular dichroism (CD) experiments. Finally, we comment 4) on the chances of switching these catenanes chemically.

Original languageEnglish (US)
Pages (from-to)3964-3979
Number of pages16
JournalChemistry - A European Journal
Issue number14
StatePublished - Jun 21 2007


  • Catenanes
  • Self-assembly
  • Spontaneous resolution
  • Supramolecular chemistry
  • Template synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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