EPR Studies of the Binding Properties, Guest Dynamics, and Inner-Space Dimensions of a Water-Soluble Resorcinarene Capsule

Mehmet Menaf Ayhan, Gilles Casano, Hakim Karoui, Antal Rockenbauer, Valérie Monnier, Micaël Hardy, Paul Tordo, David Bardelang, Olivier Ouari

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Nitroxide free radicals have been used to study the inner space of one of Rebek's water-soluble capsules. EPR and 1H NMR spectroscopy, ESI-MS, and DFT calculations showed a preference for the formation of 1:2 complexes. EPR titrations allowed us to determine binding constants (Ka) in the order of 107 M-2. EPR spectral-shape analysis provided information on the guest rotational dynamics within the capsule. The interplay between optimum hydrogen bonding upon capsule formation and steric strain for guest accommodation highlights some degree of flexibility for guest inclusion, particularly at the center of the capsule where the hydrogen bond seam can be barely distorted or slightly disturbed.

Original languageEnglish
Pages (from-to)16404-16410
Number of pages7
JournalChemistry - A European Journal
Volume21
Issue number46
DOIs
Publication statusPublished - Nov 1 2015

Keywords

  • EPR spectroscopy
  • capsules
  • host-guest systems
  • nitroxides
  • supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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