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, Francisco Raymo, J. Fraser Stoddart, Margherita Venturi, Andrew J P White, David J. Williams

Research output: Contribution to journalArticle

36 Citations (Scopus)

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
Pages (from-to)1121-1130
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number7
StatePublished - Apr 1 2000
Externally publishedYes

Fingerprint

Catenanes
templates
charge transfer
synthesis
Charge transfer
Electrons
electrons
Absorption spectra
absorption spectra
Crown Ethers
interactions
X ray analysis
ethers
emission spectra
Electrochemical properties
mass spectroscopy
Excited states
desorption
quenching
Ionization

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Ashton, P. R., Baldoni, V., Balzani, V., Claessens, C. G., Credi, A., Hoffmann, H. D. A., ... 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.

Molecular meccano, 57 : Template-directed syntheses, spectroscopic properties, and electrochemical behavior of [n]catenanes. / Ashton, Peter R.; Baldoni, Virna; Balzani, Vincenzo; Claessens, Christian G.; Credi, Alberto; Hoffmann, H. D Andreas; Raymo, Francisco; Stoddart, J. Fraser; Venturi, Margherita; White, Andrew J P; Williams, David J.

In: European Journal of Organic Chemistry, No. 7, 01.04.2000, p. 1121-1130.

Research output: Contribution to journalArticle

Ashton, PR, Baldoni, V, Balzani, V, Claessens, CG, Credi, A, Hoffmann, HDA, Raymo, F, Stoddart, JF, Venturi, M, White, AJP & Williams, DJ 2000, 'Molecular meccano, 57: Template-directed syntheses, spectroscopic properties, and electrochemical behavior of [n]catenanes', European Journal of Organic Chemistry, no. 7, pp. 1121-1130.
Ashton, Peter R. ; Baldoni, Virna ; Balzani, Vincenzo ; Claessens, Christian G. ; Credi, Alberto ; Hoffmann, H. D Andreas ; Raymo, Francisco ; Stoddart, J. Fraser ; Venturi, Margherita ; White, Andrew J P ; Williams, David J. / Molecular meccano, 57 : Template-directed syntheses, spectroscopic properties, and electrochemical behavior of [n]catenanes. In: European Journal of Organic Chemistry. 2000 ; No. 7. pp. 1121-1130.
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