Triptycene derivatives as chiral probes for studying the molecular enantiorecognition on sub-2-μm particle cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase

Alessia Rosetti; Giovanni Preda; Claudio Villani; Marco Pierini; Dario Pasini; Roberto Cirilli

doi:10.1002/chir.23358

Triptycene derivatives as chiral probes for studying the molecular enantiorecognition on sub-2-μm particle cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase

Chirality. 2021 Dec;33(12):883-890. doi: 10.1002/chir.23358. Epub 2021 Sep 27.

Authors

Alessia Rosetti¹, Giovanni Preda², Claudio Villani¹, Marco Pierini¹, Dario Pasini², Roberto Cirilli³

Affiliations

¹ Department of Chemistry and Drug Technology, Sapienza University of Rome, Rome, Italy.
² Department of Chemistry and INSTM Research Unit, University of Pavia, Pavia, Italy.
³ National Center for the Control and Evaluation of Drugs, Istituto Superiore di Sanità, Rome, Italy.

PMID: 34571576
DOI: 10.1002/chir.23358

Abstract

Two chiral triptycene derivatives were analyzed on the Chiralpak IB-U column packed with cellulose tris(3,5-dimethylphenylcarbamate)-based sub-2-μm diameter particles. Under normal-phase conditions, sub-minute baseline enantioseparations were obtained. Differences in structural elements and chromatographic behavior of the investigated compounds were evaluated to identify the interactions that drive the chiral discrimination process. From the evaluation of the experimental chromatographic data, it was found that hydrogen bond formation is essential for the separation of enantiomers.

Keywords: absolute configuration; cellulose-based CSP; chiralpak IB-U; hydrogen bonding; triptycene; ultrafast enantioselectivity.