Residual‐Chemical‐Shift‐Anisotropy‐Based Enantiodifferentiation in Lyotropic Liquid Crystalline Phases Based on Helically Chiral Polyacetylenes

Author:

Fuentes‐Monteverde Juan Carlos1ORCID,Noll Markus2,Das Akhi3ORCID,Immel Stefan2ORCID,Reggelin Michael2ORCID,Griesinger Christian1ORCID,Nath Nilamoni3ORCID

Affiliation:

1. Max Planck Institute for Multidisciplinary Sciences Department of NMR-Based Structural Biology Am Fassberg 11 37077 Göttingen Germany

2. Department of Chemistry Technical University of Darmstadt Alarich Weiss Straße 4 64287 Darmstadt Germany

3. Department of Chemistry Gauhati University Guwahati Jalukbari 781014 India

Abstract

AbstractAnisotropic NMR spectroscopy, revealing residual dipolar couplings (RDCs) and residual chemical shift anisotropies (RCSAs) has emerged as a powerful tool to determine the configurations of synthetic and complex natural compounds. The deduction of the absolute in addition to the relative configuration is one of the primary goals in the field. Therefore, the investigation of the enantiodiscriminating capabilities of chiral alignment media becomes essential. While RDCs and RCSAs are now used for the determination of the relative configuration routinely, RCSAs have not been measured in chiral alignment media such as chiral liquid crystals. Herein, we present this application by measuring RCSAs for chiral analytes such as indanol and isopinocampheol in the lyotropic liquid crystalline phase of an L‐valine derived helically chiral polyacetylenes. We have also demonstrated that a single 1D 13C−{1H} NMR spectrum suffices to get the RCSAs circumventing the necessity to acquire two spectra at two alignment conditions.

Funder

Max-Planck-Gesellschaft

Deutsche Forschungsgemeinschaft

Publisher

Wiley

Subject

General Medicine

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