A switchable hybrid [2]-catenane based on transition metal complexation and π-electron donor-acceptor interactions

David B. Amabilino, Christiane O. Dietrich-Buchecker, Aude Livoreil, Lluïsa Pérez-García, Jean Pierre Sauvage*, J. Fraser Stoddart

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

103 Scopus citations

Abstract

A bimodal [2]-catenane has been synthesized via a copper(I) templated synthesis. The compound contains both a transition metal coordination site and a set of π-electron rich and π-electron deficient aromatic units suitable for the formation of acceptor-donor complexes. Each constituent ring is thus different from the other, and the organic backbone can adopt two favored contrasting orientations by circumrotation of one ring within the other: (i) in the metal complex mode, each dpp unit (dpp = 2,9-diphenyl-1,10-phenanthroline) is entwined about the other, while a cationic species is complexed in the coordination site thus created; (ii) in the organic π-electron acceptor-donor complex mode, the dpp fragments are remote from one another, and the π-electron rich and π-electron deficient units stack to form a complex. The conversion of one binding mode to the other implies complete topographical rearrangement of the molecule. It can be triggered by adding or removing the cation center (Cu+, Li+, or H+), bonded to the dpp-containing complexing site. Interestingly, this switching process can be easily monitored by 1H NMR, since it involves drastic relative orientational changes. It can also be evidenced by electronic spectroscopy. In particular, the proton-driven rearrangement reactions lead to significant changes in the absorption spectrum, which correspond to the appearance (by deprotonation) and disappearance (by protonation of the dpp) of a charge transfer band (around 470 nm) resulting from the π-electron donor-acceptor noncovalent interaction.

Original languageEnglish (US)
Pages (from-to)3905-3913
Number of pages9
JournalJournal of the American Chemical Society
Volume118
Issue number16
DOIs
StatePublished - Apr 24 1996

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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