Enantioseparation tuned by solvent polarity on a β‐cyclodextrin clicked chiral stationary phase

Abstract

The efficient enantioseparation of 26 racemates has been achieved with the perphenylcarbamoylated cyclodextrin clicked chiral stationary phase by screening the optimum composition of mobile phase in high-performance liquid chromatography. The chromatographic results indicate that both the retention and chiral resolution of racemates are closely related to the polarity of the mobile phases and the structures of analytes. The addition of alcohols can significantly tune the enantioseparation in normal-phase high-performance liquid chromatography. The addition of methanol and the ratio of ethanol/methanol or isopropanol/methanol played a key role on the resolution of flavonoids in ternary eluent systems. The chiral separation of flavonoids with pure organic solvent as mobile phase indicates the preferential order for chiral resolution is methanol>ethanol>isopropanol>n-propanol>acetonitrile.

Cationic cyclodextrin clicked chiral stationary phase for versatile enantioseparations in high-performance liquid chromatography

“…6). The chiral recognition ability of this cationic CD-CSP was further compared with its counterpart CCC3M4-CSP as reported recently by our group [32]. Unfortunately, this cationic CD-CSP afforded worse enantioselectivities for four flavonoids than CCC3M4-CSP in both binary and ternary NP modes (see Fig.…”

“…The click preparation of MPCCC3M4-CSP was performed according to our recently reported procedure for CCC3M4-CSP [32][33][34]. As the synthetic route shown in Fig.…”

Functionalities tuned enantioselectivity of phenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC

“…The enhanced enantioseparations in RP‐HPLC were attributed to the formation of extra hydrogen bonding between ‐NH‐ and C=O in phenylcarbamate moieties, which facilitated the formation of the inclusion complex with enantiomers adopting a favorable conformation. In addition, π–π stacking and dipole–dipole interactions also contributed to the enantioseparation …”

“…The functionalities modulated enantioselectives of CD clicked CSPs have been a research theme in our group . A series of mixed chloro‐ and methyl‐substituted phenylcarbamate β‐CD clicked CSPs has been developed .…”

“…In addition, π-π stacking and dipole-dipole interactions also contributed to the enantioseparation. 4,6,23,24 The functionalities modulated enantioselectives of CD clicked CSPs have been a research theme in our group. 19,22,24 A series of mixed chloro-and methyl-substituted phenylcarbamate β-CD clicked CSPs has been developed.…”