New guests for the cucurbit[8]uril host. Formation of G 2H ternary complexes

Sanem Senler, Lu Cui, Ana Michelle Broomes, Erika L. Smith, James N. Wilson, Angel E. Kaifer

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

On the basis of the highly stable G 2H (2:1) ternary complex formed by two methyl viologen cation radicals inside the cavity of cucurbit[8]uril, we prepared three monocationic 4-phenylpyridinium derivatives: 1-(hydroxyethyl)-4-phenyl-pyridinium (1 +) bromide, 1-(octaethyleneglycol)-4-phenyl-pyridinium (2 +) chloride, and 4-[4-(methoxymethoxy)phenyl]pyridinium (3 +) iodide, as possible guests for 2:1 complexation inside cucurbit[8]uril. We also investigated a fourth monocationic guest (4 +), in which a central vinylidene group is inserted to elongate the 4-phenyl-pyridinium residue. Using 1H NMR and UV-Vis spectroscopic data and mass spectrometric data, we obtained unequivocal evidence for the formation of G 2H (2:1) ternary complexes in all cases. The stoichiometry of the complexes was further verified by continuous variation (Job) plots, and in some cases, high resolution ESI-MS spectrometric data. Diffusion coefficient measurements, using 1H NMR pulse gradient spin echo techniques, yielded values consistent with the formation and expected structures of the ternary complexes.

Original languageEnglish (US)
Pages (from-to)592-596
Number of pages5
JournalJournal of Physical Organic Chemistry
Volume25
Issue number7
DOIs
StatePublished - Jul 1 2012

Keywords

  • cucurbituril hosts
  • host-guest complexes
  • inclusion complexes
  • ternary complexes

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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