Resorcinarenes are hexameric capsules in solution

Tamar Evan-Salem, Inbal Baruch, Liat Avram, Yoram Cohen, Liam C. Palmer, Julius Rebek*

*Corresponding author for this work

Research output: Contribution to journalArticle

103 Scopus citations

Abstract

The host-guest complexes of resorcin[4]arenes with small molecules in organic solutions are examined using modern NMR spectroscopic methods. The complexation of glutaric acid and β-methyl D-glucopyranoside in chloroform were investigated through 2D COSY, 2D NOESY, 1D NOE, and diffusion-ordered NMR spectroscopy (DOSY) techniques. These methods indicate that the complex is a self-assembled capsule composed of six resorcinarenes that surround six guest molecules of glutaric acid or three molecules of β-methyl D-glucopyranoside inside. The multiplicity of guest proton signals shows that the capsule provides an asymmetric magnetic environment that persists on the 1H NMR time scale. The encapsulation of these guests and common solvents suggests that the phenomenon of reversible encapsulation in chemistry may be a century old.

Original languageEnglish (US)
Pages (from-to)12296-12300
Number of pages5
JournalProceedings of the National Academy of Sciences of the United States of America
Volume103
Issue number33
DOIs
StatePublished - Aug 15 2006

Keywords

  • Diffusion spectroscopy
  • Encapsulation
  • Self-assembly

ASJC Scopus subject areas

  • General

Fingerprint Dive into the research topics of 'Resorcinarenes are hexameric capsules in solution'. Together they form a unique fingerprint.

  • Cite this