Manifesting Subtle Differences of Neutral Hydrophilic Guest Isomers in a Molecular Container by Phase Transfer

Hyun Hee L. Lee, Jong Wha Lee, Yoonjung Jang, Young Ho Ko, Kimoon Kim, Hugh I. Kim

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Achieving strong host–guest interactions between synthetic hosts and hydrophilic guests in solution is challenging because solvation effects overwhelm other effects. To resolve this issue, we transferred complexes of cucurbit[7]uril (CB[7]) and monosaccharides to the gas phase and report here their intrinsic host–guest chemistry in the absence of solvation effects. It was observed that effective host–guest interactions in the gas phase mediated by ammonium cations allow the differentiation of the monosaccharide isomers in complex with CB[7] upon vibrational excitation. The potential of the unique observation was extended to a quantitative supramolecular analytical method for the monosaccharide guests. The combination of host–guest chemistry and phase transfer presented in this study is an effective approach to overcome current limitations in supramolecular chemistry.

Original languageEnglish
Pages (from-to)8249-8253
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number29
DOIs
Publication statusPublished - 2016 Jan 1

Keywords

  • cucurbit[7]uril
  • gas-phase chemistry
  • host–guest systems
  • mass spectrometry
  • monosaccharides

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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