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Chiral separation of novel diazenes on a polysaccharide‐based stationary phase in the reversed‐phase mode
Author(s) -
Vojtylová Terézia,
Hamplová Věra,
Galewski Zbigniew,
Korbecka Izabela,
Sýkora David
Publication year - 2017
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.201601386
Subject(s) - enantiomer , chemistry , moiety , phase (matter) , chromatography , chiral resolution , resolution (logic) , chiral stationary phase , chiral column chromatography , chirality (physics) , analytical chemistry (journal) , organic chemistry , stereochemistry , chiral symmetry breaking , physics , quantum mechanics , artificial intelligence , computer science , nambu–jona lasinio model , quark
Chiral high‐performance liquid chromatography separation of two recently synthesized liquid crystalline materials C1 and C2 was studied in the reversed‐phase mode. Both materials have an azo‐moiety and one chiral center in their molecular structures. They were available in racemic and pure S forms. For the enantiomeric separations, a Chiralpak AY‐RH stationary phase based on amylose tris(5‐chloro‐2‐methylphenylcarbamate) coated on 5 μm silica was used. The compounds were analyzed in both of their possible forms, the more thermodynamically stable E form and the labile Z form. The conditions and time scale of the UV‐induced E to Z transition were briefly evaluated. Under the optimized conditions, we were able to baseline separate S and R enantiomers of both of the studied materials not only in their E forms, but also in their Z forms. In comparison to the separation in the normal‐phase mode, which we have reported recently, the resolution in the reversed‐phase mode is significantly better. Interestingly, peak reversal was noticed for the S and R enantiomers when the separation was carried out with E versus Z forms of both compounds.