Controlled dethreading/rethreading of a scorpion-like pseudorotaxane and a related macrobicyclic self-complexing system

V. Balzani*, P. Ceroni, A. Credi, M. Gómez-López, C. Hamers, J. F. Stoddart, R. Wolf

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

A scorpion-like pseudorotaxane (1 · H2+), composed of a macrocyclic polyether containing a 1,5-dioxynaphthalene (1,5-DON) and a 1,3-dioxybenzene (1,3-DOB) electron-donor unit, the latter bearing a 4,4′-bipyridinium electron-acceptor tail, underwent threading/dethreading motions under control of (i) solvent polarity and (ii) solution acidity. Furthermore, the complexation of 1 · H2+ with the trans-1,2-bis(1-benzyl-4-pyridinio)ethylene electron acceptor can be acid/base controlled. The spectroscopic properties of a related macrobicyclic compound 24+ (comprised of an electron-donor and an electron-acceptor macrocycle that share a benzene ring) have also been investigated. The results obtained for 24+ are consistent with the presence of intramolecular self-complexed species where the electron-donor macrocycle is threaded through the electron-acceptor one. Electrochemical experiments confirm the self-complexing structures of 1 · H2+ and 24+. It seems likely that both compounds undergo decomplexation upon electrochemical stimulation.

Original languageEnglish (US)
Pages (from-to)25-31
Number of pages7
JournalNew Journal of Chemistry
Volume25
Issue number1
DOIs
StatePublished - Mar 1 2001

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

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