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Poly(arylisocyanides) as Versatile, Enantiodiscriminating Alignment Media for Small Molecules

Wesp, Svenja ; Wolf, Kai ; Immel, Stefan ; Reggelin, Michael (2022):
Poly(arylisocyanides) as Versatile, Enantiodiscriminating Alignment Media for Small Molecules. (Publisher's Version)
In: ChemPlusChem, 87 (1), Wiley-VCH, e-ISSN 2192-6506,
DOI: 10.26083/tuprints-00021547,
[Article]

Abstract

Lyotropic liquid crystalline (LLC) phases of amino acid derived polyarylisocyanides were employed as chiral alignment media for the measurement of residual dipolar couplings (RDCs) of small chiral organic molecules. Anisotropic samples in CDCl₃ displayed quadrupolar splittings of the deuterium signal in the range of several hundreds of Hertz. The LLC phases showed excellent orienting properties for a broad range of analytes bearing various functional groups. The precise extraction of RDCs in the range of up to ±40 Hertz from F2‐coupled HSQC spectra was possible. Additionally, the chiral environment offers the opportunity for diastereomorphous interactions with the enantiomers of chiral analytes leading to two different sets of RDCs. This differential order effect was particularly pronounced with ketones and alcohols.

Item Type: Article
Erschienen: 2022
Creators: Wesp, Svenja ; Wolf, Kai ; Immel, Stefan ; Reggelin, Michael
Origin: Secondary publication DeepGreen
Status: Publisher's Version
Title: Poly(arylisocyanides) as Versatile, Enantiodiscriminating Alignment Media for Small Molecules
Language: English
Abstract:

Lyotropic liquid crystalline (LLC) phases of amino acid derived polyarylisocyanides were employed as chiral alignment media for the measurement of residual dipolar couplings (RDCs) of small chiral organic molecules. Anisotropic samples in CDCl₃ displayed quadrupolar splittings of the deuterium signal in the range of several hundreds of Hertz. The LLC phases showed excellent orienting properties for a broad range of analytes bearing various functional groups. The precise extraction of RDCs in the range of up to ±40 Hertz from F2‐coupled HSQC spectra was possible. Additionally, the chiral environment offers the opportunity for diastereomorphous interactions with the enantiomers of chiral analytes leading to two different sets of RDCs. This differential order effect was particularly pronounced with ketones and alcohols.

Journal or Publication Title: ChemPlusChem
Journal Volume: 87
Issue Number: 1
Place of Publication: Darmstadt
Publisher: Wiley-VCH
Collation: 8 Seiten
Uncontrolled Keywords: anisotropic phases, helical chirality, lyotropic liquid crystals, NMR, polymers
Divisions: 07 Department of Chemistry
07 Department of Chemistry > Organ Chemistry
Date Deposited: 24 Jun 2022 12:45
DOI: 10.26083/tuprints-00021547
URL / URN: https://tuprints.ulb.tu-darmstadt.de/21547
URN: urn:nbn:de:tuda-tuprints-215479
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