Oligoindole-based foldamers with a helical conformation induced by chloride

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

Research output: Contribution to journalArticle

162 Citations (Scopus)

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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Conformations
Chlorides
Titration
Hydrogen bonds
Indoles
Experiments
Hydrogen Bonding
Nuclear magnetic resonance
Association reactions
Hydrogen
indole

All Science Journal Classification (ASJC) codes

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

Cite this

Chang, Kyoung Jin ; Kang, Byung Nam ; Lee, Min Hee ; Jeong, Kyu Sung. / Oligoindole-based foldamers with a helical conformation induced by chloride. In: Journal of the American Chemical Society. 2005 ; Vol. 127, No. 35. pp. 12214-12215.
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Oligoindole-based foldamers with a helical conformation induced by chloride. / Chang, Kyoung Jin; Kang, Byung Nam; Lee, Min Hee; Jeong, Kyu Sung.

In: Journal of the American Chemical Society, Vol. 127, No. 35, 07.09.2005, p. 12214-12215.

Research output: Contribution to journalArticle

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