Effective HPLC resolution of [4]heterohelicenium dyes on chiral stationary phases using reversed-phase eluents.
[4]Heterohelicenium cations 1a-c adopt a twisted helical structure that renders them chiral. They are configurationally stable and their enantiomers have been resolved, for the first time, by HPLC on Chiralcel OD-RH and Chirobiotic TAG chiral stationary phases (CSPs). Chiral cations 1a-c have been resolved by HPLC using water-based eluents containing KPF(6) as additive. The elution order of the analyte enantiomers was determined by on-line CD detection, and was found to be opposite on the two CSPs. The effect of mobile phase composition and analyte structure on retention and enantioselectivity was investigated.
Villani
Claudio
C
Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università di Roma La Sapienza, Roma, Italy. claudio.villani@uniroma1.it
Laleu
Benoît
B
Mobian
Pierre
P
Lacour
Jérôme
J
D002851:Chromatography, High Pressure Liquid / Q000379:methods; D002942:Circular Dichroism; D004396:Coloring Agents / Q000737:chemistry / Q000302:isolation & purification*; D008968:Molecular Conformation; D011083:Polycyclic Compounds / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism
D004396:Coloring Agents; D011083:Polycyclic Compounds; C031660:helicenes