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Novel Pirkle‐type quinine 3,5‐dinitrophenylcarbamate chiral stationary phase implementing click chemistry
Author(s) -
Kacprzak Karol M.,
Lindner Wolfgang
Publication year - 2011
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.201100395
Subject(s) - chemistry , click chemistry , moiety , combinatorial chemistry , selectivity , triazole , cycloaddition , cyclodextrin , quinoline , organic chemistry , catalysis
A new Pirkle‐anion exchange hybrid‐type chiral stationary phase (CSP‐1) has been synthesized by immobilizing 10,11‐didehydroquinine 3,5‐dinitrophenylcarbamate onto 3‐azidopropyl silica gel using click chemistry (1,3‐dipolar Huisgen cycloaddition). This chiral selector and CSP contain a strong π‐accepting 3,5‐dinitrophenyl residue besides the π‐basic quinoline group and an ionizable tertiary amino group. In concert with ion pairing it offers π‐donor–π‐acceptor interactions resulting in an enhancement of the selectivity toward specific π‐donating analytes such as aryloxypropionic acids and profens. A representative set of these analytes has been investigated under various chromatographic conditions (polar‐organic, reversed‐ and normal‐phase) leading to base‐line enantioseparations with selectivity (α) values up to 1.8. Control experiments with related quinine tert ‐butylcarbamate phase grafted onto the surface either by thioether (Chiralpak QN‐AX) or 1,2,3‐triazole linker revealed the impact of the additional aromatic moiety in the chiral selector motif.