Indolocarbazole-based foldamers capable of binding halides in water

Jae Min Suk, Kyu Sung Jeong

Research output: Contribution to journalArticle

114 Citations (Scopus)

Abstract

A series of indolocarbazole-based foldamers have been prepared which can fold into a helical array with an internal cavity encircled by multiple indole NHs, thus allowing for binding anions by hydrogen bonds. The helical folding has been confirmed by computer modeling, 1H NMR spectroscopy, 2D ROESY experiments, and binding studies. A water-soluble derivative binds small, hydrophilic anions in the order Cl- > F- > Br- but negligibly with large, diffuse anions such as I- and ClO4-. Interestingly, the relative binding affinities of the fluoride and chloride ions in water are opposite to each other in an organic medium 4:1 (v/v) DMSO/MeOH, possibly due to the difference in the competing solvation energy.

Original languageEnglish
Pages (from-to)11868-11869
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number36
DOIs
Publication statusPublished - 2008 Sep 10

All Science Journal Classification (ASJC) codes

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

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