Molecular meccano, 57: Template-directed syntheses, spectroscopic properties, and electrochemical behavior of [n]catenanes

Peter R. Ashton, Virna Baldoni, Vincenzo Balzani, Christian G. Claessens, Alberto Credi, H. D.Andreas Hoffmann, Françisco M. Raymo, J. Fraser Stoddart, Margherita Venturi, Andrew J.P. White, David J. Williams

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

Catenanes composed of two, three, five, or seven interlocked macrocycles have been synthesized in yields ranging from 1 to 30%. Their template- directed syntheses rely on a series of cooperative noncovalent bonding interactions between π-electron rich 1,5-dioxynaphthalene ring systems and π-electron deficient bipyridinium units which are incorporated within the macrocyclic components. The interlocked structure associated with one of the [3]catenanes was demonstrated unequivocally by single crystal X-ray analysis which also revealed the formation of polar stacks stabilized by intermolecular [π···π] interactions. The number of interlocked components of each catenane was determined by liquid secondary ion, matrix- assisted laser desorption ionization/time-of-flight, and/or electrospray mass spectrometries. The absorption spectra, emission spectra, and electrochemical properties of the macrocyclic components and of the catenanes have been investigated. Two kinds of charge-transfer absorption bands (intramolecular in the cyclophanes containing electron-donor and electron-acceptor units, intercomponent in the catenanes) have been found. Such charge-transfer excited states are responsible for the quenching of the potentially fluorescence units of the cyclophanes, and of the crown ethers in the catenanes. Charge-transfer electronic interactions are also evidenced by the electrochemical behavior. Correlations among the redox potentials of the various compounds are reported and discussed.

Original languageEnglish (US)
Pages (from-to)1121-1130
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number7
DOIs
StatePublished - Apr 2000
Externally publishedYes

Keywords

  • Catenanes
  • Cyclophanes
  • Electrochemistry
  • Electronic spectroscopy
  • Template- directed synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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    Ashton, P. R., Baldoni, V., Balzani, V., Claessens, C. G., Credi, A., Hoffmann, H. D. A., Raymo, F. M., Stoddart, J. F., Venturi, M., White, A. J. P., & Williams, D. J. (2000). Molecular meccano, 57: Template-directed syntheses, spectroscopic properties, and electrochemical behavior of [n]catenanes. European Journal of Organic Chemistry, (7), 1121-1130. https://doi.org/10.1002/1099-0690(200004)2000:7<1121::aid-ejoc1121>3.0.co;2-3