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Author

Lah, Myoung Soo
Nanoporous Materials Lab
Research Interests
  • Metal-Organic Frameworks (MOFs)

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A Foldamer-Based Chiroptical Molecular Switch That Displays Complete Inversion of the Helical Sense upon Anion Binding

Cited 52 times inthomson ciCited 44 times inthomson ci
Title
A Foldamer-Based Chiroptical Molecular Switch That Displays Complete Inversion of the Helical Sense upon Anion Binding
Author
Suk, Jae-minNaidu, Veluru RameshLiu, XinfangLah, Myoung SooJeonet, Kyu-Sung
Keywords
Absolute stereochemistry; Anion binding; Binding modes; CD spectra; H NMR spectra; Helical conformation; Helical sense; Indolocarbazoles; Intramolecular hydrogen bond; Molecular switches; Single crystal x-ray structures; Sulfate complexes; Sulfate ion
Issue Date
201109
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.133, no.35, pp.13938 - 13941
Abstract
Chiral indolocarbazole dimers fold into a helical conformation by virtue of intramolecular hydrogen bonds, as demonstrated by (1)H 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 (1)H NMR spectra in solution.
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DOI
http://dx.doi.org/10.1021/ja206546b
ISSN
0002-7863
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