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 journalArticle

22 Scopus citations

Abstract

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
Volume13
Issue number14
DOIs
StatePublished - Jun 21 2007

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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