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Residual-Chemical-Shift-Anisotropy-Based Enantiodifferentiation in Lyotropic Liquid Crystalline Phases Based on Helically Chiral Polyacetylenes.
Angew Chem Int Ed Engl
November 2023
Department of Chemistry, Gauhati University Guwahati, Jalukbari, 781014, India.
Anisotropic 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.
View Article and Find Full Text PDFSelf-Assembly of Helical Polymers and Oligomers to Create Liquid Crystalline Alignment for Anisotropic NMR Parameters.
Macromol Rapid Commun
July 2022
State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, Jilin Province, 130012, China.
The measurement of anisotropic residual dipolar couplings (RDCs) parameters for the structure elucidation of organic molecules relies on suitable alignment media. Employment of self-assembled liquid crystalline systems to create anisotropic alignment can be an effective way to realize aligned samples and acquire RDCs. This Mini-review highlights the recent advances on amino acid-based helical polymers and supramolecular oligomers forming rigid, rod-like structures that aggregate into ordered liquid crystalline phases, including amino acid-based helical polyisocyanides, polyacetylenes, polypeptides, and oligopeptides assembled alignment media.
View Article and Find Full Text PDFOptically active porous hybrid particles constructed by alkynylated cellulose nanocrystals, helical substituted polyacetylene, and inorganic silica for enantio-differentiating towards naproxen.
Chirality
January 2022
State Key Laboratory of Chemical Resource Engineering and College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing, China.
This article reports on a novel type of ternary chiral porous hybrid particles (TCPHPs) constructed by alkynylated cellulose nanocrystals (A-CNCs), helical substituted polyacetylene, and inorganic silica. The resulting TCPHPs combine the respective advantages of the three components. A-CNCs serve as stabilizer, co-monomer, and chiral source simultaneously and transfer their chirality to the resulting helical substituted polyacetylenes in the course of copolymerization with achiral acetylenic monomer following "sergeants and soldiers rule".
View Article and Find Full Text PDFValine derived poly (acetylenes) as versatile chiral lyotropic liquid crystalline alignment media for RDC-based structure elucidations.
Magn Reson Chem
May 2021
Clemens Schöpf Institut for Organic Chemistry and Biochemistry, Technical University of Darmstadt, Darmstadt, Germany.
Anisotropic samples of lyotropic liquid crystalline (LLC) phases of valine derived polyaryl acetylenes were employed as chiral alignment media for the measurement of residual dipolar couplings (RDCs) of 12 small, chiral, organic molecules. The quadrupolar splitting of the deuterium signal of CDCl can be adjusted by temperature and concentration changes from 0 to 350 Hz. The LLC phases showed excellent orienting properties for all analytes bearing various functional groups.
View Article and Find Full Text PDFH and C NMR-Based Enantiodetection Using Polyacetylene versus Polypeptide Aligning Media: Versatile and Complementary Tools for Chemists.
Chempluschem
February 2019
Clemens-Schöpf-Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Alarich-Weiss-Strasse 4, 64287, Darmstadt, Germany.
Invited for this month's cover are the collaborating groups of Dr. Philippe Lesot (DR CNRS) at Université Paris-Sud/Université Paris-Saclay, France, and Professor Michael Reggelin at TU Darmstadt, Germany. The cover shows the proton-decoupled natural abundance deuterium (NAD-{ H}) Q-resolved Fz 2D-NMR spectrum of (±)-3-methylhexane measured in the anisotropic lyotropic chiral liquid-crystalline phase formed by a concentrated solution of a helically chiral polyarylacetylene in chloroform solvent.
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