A foldamer-based chiroptical molecular switch that displays complete inversion of the helical sense upon anion binding

Jae Min Suk, Veluru Ramesh Naidu, Xinfang Liu, Myoung Soo Lah, Kyu Sung Jeong

Research output: Contribution to journalArticle

122 Citations (Scopus)

Abstract

Chiral indolocarbazole dimers fold into a helical conformation by virtue of intramolecular hydrogen bonds, as demonstrated by 1H NMR and CD spectra and optical rotations. In particular, the optical properties of the dimers were found to be extremely sensitive to the nature of the solvent, depending on whether they are folded or not. The helical sense of the dimers can be reversibly switched by binding sulfate ion, which gives rise to complete inversion of the CD spectra. The binding mode and absolute stereochemistry of the sulfate complexes was unequivocally determined by single-crystal X-ray structures, which are all consistent with the CD and 1H NMR spectra in solution.

Original languageEnglish
Pages (from-to)13938-13941
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number35
DOIs
Publication statusPublished - 2011 Sep 7

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Dimers
Sulfates
Anions
Negative ions
Switches
Optical Rotation
Nuclear magnetic resonance
Optical rotation
Hydrogen
Stereochemistry
X-Rays
Ions
Conformations
Hydrogen bonds
Optical properties
Single crystals
X rays
Proton Magnetic Resonance Spectroscopy

All Science Journal Classification (ASJC) codes

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

Cite this

Suk, Jae Min ; Naidu, Veluru Ramesh ; Liu, Xinfang ; Lah, Myoung Soo ; Jeong, Kyu Sung. / A foldamer-based chiroptical molecular switch that displays complete inversion of the helical sense upon anion binding. In: Journal of the American Chemical Society. 2011 ; Vol. 133, No. 35. pp. 13938-13941.
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A foldamer-based chiroptical molecular switch that displays complete inversion of the helical sense upon anion binding. / Suk, Jae Min; Naidu, Veluru Ramesh; Liu, Xinfang; Lah, Myoung Soo; Jeong, Kyu Sung.

In: Journal of the American Chemical Society, Vol. 133, No. 35, 07.09.2011, p. 13938-13941.

Research output: Contribution to journalArticle

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