Synthesis and characterization of a novel resorcinarene-based stationary phase bearing polar headgroups for use in reversed-phase high-performance liquid chromatography

Ruderisch, Alexander; Iwanek, Waldemar; Pfeiffer, Jens; Fischer, Gert; Albert, Klaus; Schurig, Volker

doi:10.1016/j.chroma.2005.07.109

Cited by 42 publications

(22 citation statements)

References 19 publications

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“…Several recent papers have addressed the characterisation and comparison of novel polar-embedded stationary phases [9][10][11][12][13]. These stationary phases contain a polar functionality, such as an amide, carbamate, urea, sulphonamide or phenyl ether group, directly linked to the alkyl chain in close proximity to the silica surface.…”

Section: Introductionmentioning

confidence: 99%

Use of a polar-embedded stationary phase for the separation of tocopherols by CEC

Carabias‐Martínez¹,

Rodríguez‐Gonzalo²,

Smith³

et al. 2006

Electrophoresis

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A polar-embedded stationary phase (ULTIMA C18) has been investigated for the separation of alpha-, beta-, gamma- and delta-tocopherols by CEC in comparison with commercially available C(18) and C(30) n-alkyl RPs. The behavior of this stationary phase was tested for different mobile phases based on methanol, ACN, or mixtures thereof and different separation parameters such as retention factors and resolution were evaluated. The main feature of this stationary phase is the improved selectivity for the separation of beta- and gamma-tocopherols (positional isomers) when compared with the pure n-alkyl C(18) material, which was unable to resolve these compounds. Additionally, it is possible to observe a reversal in the elution order of the beta- and gamma-tocopherol isomers with respect to that obtained on the C(30) column. The resulting data indicate that the enhanced selectivity obtained with the polar-embedded stationary phase, with respect to the conventional C(18) material, is due to the participation of both hydrophobic and polar interactions: these latter are of the hydrogen bridge type with the amide group of the polar-embedded stationary phase, which increases the retention of the tocopherols and facilitates the discrimination between the beta- and gamma-isomers. Adequate separation of the four tocopherols was obtained by CEC using the polar-embedded stationary phase and 95:5 v/v methanol/water (5 mM Tris, final concentration) as the mobile phase.

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Section: Introductionmentioning

confidence: 99%

Use of a polar-embedded stationary phase for the separation of tocopherols by CEC

Carabias‐Martínez¹,

Rodríguez‐Gonzalo²,

Smith³

et al. 2006

Electrophoresis

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“…The family of calix [4]resorcinarenes has also been used for various functions such as additive for capillary electrophoresis, 10 liquid membrane, 11,12 extraction, 13 chemical sensing, 14,15 and HPLC stationary phase. 16,17 Nonetheless, there are still limited reports on the utilization of calix [4]resorcinarenes 18 as adsorbent for heavy metal cations. C-Methylcalix [4]resorcinarene (CMCR) is calix [4]resorcinarene having four benzene rings and eight hydroxyl groups (Fig.…”

Section: Introductionmentioning

confidence: 99%

Adsorption Characteristics of Pb(II) and Cr(III) onto C-Methylcalix[4]resorcinarene

Jumina¹,

Sarjono²,

Siswanta³

et al. 2011

Journal of the Korean Chemical Society

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has been conducted. CMCR was produced by one step synthesis from resorcinol, acetaldehyde, and HCl. Most parameters in batch system confirm that CMCR is a good adsorbent for Pb(II) and Cr(III). Cr(III) uptake was bigger than that of Pb(II), but Cr(III) adsorption rate was slower than Pb(II). The adsorption kinetic of Pb(II) and Cr(III) adsorptions in batch followed pseudo 2 nd order kinetics model, but the kinetic of Pb(II) adsorption in fixed bed column system followed first order model. Desorption studies to recover the adsorbed Pb(II) was performed sequentially with distilled water and HCl, and the results showed that the adsorption was dominated by chemisorption.

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“…Some other interactions, e.g., p-p interaction, 14 hydrogen-bonding interaction, and host-guest interaction, may play an important role for separation of the positional isomers under normal-phase conditions. 18 …”

Section: Results and Discussion Evaluation Of The New Stationary Phasmentioning

confidence: 97%

“…14 Compared with commercially available reversed-phase stationary phases, a new carbamate-functionalized resorcinarene-bonded silica stationary phase exhibited different retention characteristics because of multiple interaction mechanisms available for the new phase. 18 Because MCR has more phenol groups than calixarene and because MCR can easily introduce more chiral centers than resorcinarene when linked to a spacer ligand, we hypothesize that the MCR-based silica particles can exhibit better chromatographic performance than the previously reported calixarene-and resorcinarene-bonded silica particles when used as CSPs in HPLC.…”

Section: Introductionmentioning

confidence: 98%

Preparation and application of methylcalix[4]resorcinarene‐bonded silica particles as chiral stationary phase in high‐performance liquid chromatography

et al. 2011

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Two new types of methylcalix[4]resorcinarene-bonded stationary phases, (3-(C-methylcalix[4]resorcinarene)-2-hydroxypropoxy)-propylsilyl-appended silica particles (MCR-HPS) and bromoacetate-substituted MCR-HPS particles (BAMCR-HPS), have been synthesized and used as chiral stationary phases for high-performance liquid chromatography (HPLC) for the first time. The synthetic stationary phases are characterized by means of elemental analysis and Fourier-transform infrared spectroscopy. The chromatographic behavior of MCR-HPS and BAMCR-HPS was studied with several disubstituted benzenes and some chiral drug compounds under both normal phase and reversed-phase conditions. The results show that MCR-HPS has excellent selectivity for the separation of aromatic positional isomers and BAMCR-HPS exhibits excellent performance for separation of enantiomers of chiral compounds.

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Synthesis and characterization of a novel resorcinarene-based stationary phase bearing polar headgroups for use in reversed-phase high-performance liquid chromatography

Cited by 42 publications

References 19 publications

Use of a polar-embedded stationary phase for the separation of tocopherols by CEC

Use of a polar-embedded stationary phase for the separation of tocopherols by CEC

Adsorption Characteristics of Pb(II) and Cr(III) onto C-Methylcalix[4]resorcinarene

Preparation and application of methylcalix[4]resorcinarene‐bonded silica particles as chiral stationary phase in high‐performance liquid chromatography

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