Synthesis of fullerodendrons with an ammonium unit at the focal point and their cooperative self-assembly on a fluorescent ditopic crown ether receptor

Jean François Nierengarten, Uwe Hahn, Ali Trabolsi, Haiko Herschbach, François Cardinali, Mourad Elhabiri, Emmanuelle Leize, Alain Van Dorsselaer, Anne Marie Albrecht-Gary

Research output: Contribution to journalArticlepeer-review

Abstract

Dendritic branches with 1, 2, or 4 peripheral fullerene subunits and an ammonium function at the focal point have been prepared. Their ability to form self-assembled dendritic structures with oligophenylenevinylene receptors bearing one or two crown ether moieties has been evidenced by ES-MS studies for the first time. These supramolecular complexes are multicomponent photoactive devices in which the emission of the central receptor is dramatically quenched by the fullerene units. This new property resulting from the association of the different molecular subunits allowed detailed investigations of the self-assembly process by means of fluorescence titrations. The binding studies have revealed positive cooperative effects for the assembly of the fullerodendrimers with the ditopic receptor. Interestingly, the stability of the supramolecular 2:1 structures increases as the size of the dendritic unit increases. This positive dendritic effect has been explained by the larger number of possible intramolecular fullerene-fullerene interactions between the two dendritic guests when the number of fullerene subunits is increased.

Original languageEnglish (US)
Pages (from-to)3365-3373
Number of pages9
JournalChemistry - A European Journal
Volume12
Issue number12
DOIs
StatePublished - Apr 12 2006

Keywords

  • Cooperative phenomena
  • Crown compounds
  • Dendrimers
  • Fullerenes
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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