Oligoindole-based foldamers with a helical conformation induced by chloride

Kyoung Jin Chang, Byung Nam Kang, Min Hee Lee, Kyu Sung Jeong

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Abstract

As a new type of foldamers, oligoindoles containing 4, 6, and 8 indole rings were synthesized, and their folding properties were characterized by a combination of 1H NMR techniques and UV/visible titration experiments. When chloride was added, the NH signals of the oligoindoles were downfield shifted as a result of hydrogen-bond formation, and the aromatic signals were upfield shifted by stacking between two indoles. Moreover, the ROESY experiment provided definitive NOE evidence for the helical stacking in the presence of chloride. Finally, the UV/visible titration experiments demonstrated that the oligoindoles formed 1:1 complexes with chloride, and the association constants greatly increased with increasing the number of the indole NHs. These observations are all consistent with the fact that oligoindoles adopt a helical conformation when complexed with chloride by hydrogen-bonding interactions.

Original languageEnglish
Pages (from-to)12214-12215
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number35
DOIs
Publication statusPublished - 2005 Sep 7

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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