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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

37 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

Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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