Metallomacrocycles that incorporate cofacially aligned diimide units

Meisa S. Khoshbin, Maxim V. Ovchinnikov, Khalid S. Salaita, Chad A. Mirkin*, Charlotte L. Stern, Lev N. Zakharov, Arnold L. Rheingold

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

Pyromellitic diimide and naphthalene diimide moieties were incorporated into hemilabile phosphanylalkyl thioether ligands. These ligands reacted with [Cu(CH3CN)PF6 and [Rh(NBD)Cl]2 (NBD = norbornadiene) by the weak-link approach to form condensed intermediates. Upon reaction of each diimide ligand with these transition-metal precursors, the two diimide units became cofacially aligned within a supramolecular macrocyclic architecture. The introduction of ancillary ligands to each of these condensed intermediates caused the weak thioether-metal bonds to break, thus general ing a large macrocycle in which the distance between diimide units is significantly larger than for the condensed intermediates. The two Rh1 cationic condensed intermediates were characterized by single-crystal X-ray diffraction studies, and the electrochemical activity of these macrocycles was demonstrated with the naphthalene diimide-Cu1 macrocycles.

Original languageEnglish (US)
Pages (from-to)686-692
Number of pages7
JournalChemistry - An Asian Journal
Volume1
Issue number5
DOIs
StatePublished - Dec 11 2006

Keywords

  • Electron-deficient compounds
  • Hemilabile ligands
  • Macrocycles
  • Metallacycles
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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