New calixarene-bonded stationary phases in high-performance liquid chromatography: comparative studies on the retention behavior and on influences of the eluent

Sokoließ, Torsten; Menyes, Ulf; Roth, U.; Jira, Thomas

doi:10.1016/s0021-9673(00)00875-x

Cited by 52 publications

(47 citation statements)

References 30 publications

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“…The ability of the calixarenes to form complexes with other molecules and the possibility of choosing a cavity of suitable size as well as hydrophobicity makes the calixarenes a useful class of HPLC stationary phases when pharmaceutical compounds are to be separated [4,5]. Calixarene-based stationary phases have also proven to be superior in their separation of structurally similar compounds such as o, m, p-substituted aromatics [6 -9], polyaromatic hydrocarbons [4,9,10], cis/trans-isomers of dipeptides [11], and thioxanthenes [5] compared to conventional C 18 phases [4,6,8,11].…”

Section: Introductionmentioning

confidence: 99%

Investigation of the retention behaviour of steroids with calixarene‐based stationary phases by modern NMR spectroscopy

Skogsberg

Händel

Gesele

et al. 2003

J of Separation Science

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Investigation of the retention behaviour of steroids with calixarene-based stationary phases by modern NMR spectroscopy A separation of four structurally similar steroids was performed on two calix[8]arene based stationary phases. It was observed that two of the steroids had a reversed retention order when the columns were changed. This implies that two different retention mechanisms are taking place when the analytes are separated. In order to evaluate the mechanism responsible for the reversal of the retention order an extensive study of the interactions between the stationary phases and the analytes was undertaken. By performing a series of transferred NOESY measurements in the suspended state valuable information was obtained about the strengths of the interactions between the analytes and the stationary phases. The magnitudes of the integrals from the trNOESY measurements showed a good correlation with the k9 values obtained from the chromatographic evaluation. The retention mechanism is based mainly on hydrophobic interactions. However, the reversal of the elution order was mainly due to an additional p-p interaction between one of the analytes and the stationary phase.

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Section: Introductionmentioning

confidence: 99%

Investigation of the retention behaviour of steroids with calixarene‐based stationary phases by modern NMR spectroscopy

Skogsberg

Händel

Gesele

et al. 2003

J of Separation Science

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“…Figure 10 illustrates the effect of the resolution (Rs) for the four PAHs against the ACN concentration in C[4]-TMOS-VTMS column. As the ACN concentration increased from 20 to 50%, resolution for all the solutes increased and reached the maximum, whereas further increase in ACN from 50 to 70% would severely damage resolution, which might be explained that part of organic modifier is possibly included into cavity of the calixarene [47]. Such inclusion complex may influence the host-guest interactions toward solutes [48].…”

Section: Pahsmentioning

confidence: 99%

Calix[4] open‐chain crown ether‐modified, vinyl‐functionalized hybrid silica monolith for capillary electrochromatography

et al. 2008

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A novel calix[4] open-chain crown ether (p-tert-butylcalix[4]arene-1,3-bis(allyloxyethy) ether)-modified, organic-inorganic hybrid silica-based monolithic column possessing vinyl ligands for CEC is described. The monolithic silica matrix containing a vinyl functionality was synthesized by in situ cocondensation of tetramethoxysilane (TMOS) and vinyltrimethoxysilane (VTMS) via sol-gel process and chemically modified with calix[4] open-chain crown ether by free radical polymerization procedure using alpha, alpha'-azobisisobutyronitrile (AIBN) as an initiator. Morphology of the monolithic column was examined by SEM and the successful incorporation of calix[4] open-chain crown ether to the vinyl-hybrid monolith was characterized by infrared (IR) spectra. Compared with an unmodified vinyl-hybrid monolithic column, slightly stronger EOF at pH >7.5 was observed for this monolithic column due to the ionization of phenolic hydroxyls on the lower rim of calix[4]arene. VTMS/TMOS ratios in the reaction mixture were varied and 1:4 was found to be optimum to obtain homogeneous monolith with good permeability. The performance of the column was evaluated by nucleotides, beta-blockers, neurotransmitters, and PAHs as test solutes and compared with that of unmodified vinyl-hybrid monolithic column. Greatly improved column performance was obtained due to the host-guest interaction and intermolecular hydrogen bonding provided by the calix[4] open-chain crown ether moiety. The column efficiencies for neurotransmitters and nucleotides are up to 120 000 and 110 000 plates/m, respectively. Migration time and theoretical plate number reproducibilities were reasonable with RSDs less than 1.0 and 1.8% each for within column runs and not more than 7.2 and 8.6% each for column-to-column measurements, using four nucleotides as test solutes.

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“…The resulting solution was filtered through 0.22 μm filter and the filtrate (10 μL) was ready for analysis. p-tert-butyl-calix [8]arene steroids [25] calix [6]arene-p-sulfonate nitrophenol, methoxyphenol, cresol, aminophenol and chlorophenol [26] C-tetraundecylcalix [4]resorcinarene cytosine, uracil and thymine [27] calix [8]arene tricyclic neuroleptic [28] calix [4]arenes benzene or uracil derivatives [29] caltrex BIIE paracetamol, caffeine and acetylsalicylic acid [30] caltrex AIII celecoxib [31] fluorinated calix [4]arene fluorine compounds [32] p-tert-butyl-calix [8]arene aromatic carboxylic acids [33] 9-amino(9-deoxy)-epiquinine calix [4]arene, 9-amino(9-deoxy)-quinine calix [4]arene cyclic amino acids [34] caltrex AI, caltrex AII, caltrex AIII, caltrex BI, caltrex BII and caltrex BIII PAHs, phenols, substituted aromatics, xanthines, barbituric acid, benzoic acid esters [35] calix [4]arene tetradiethylamide amino acid ester hydrochlorides [36,37] calix [4]resorcinarene and calix [4,6,8]arene flupentixol, chlorprothixene, clopenthixol, and doxepin [38] p-tert-butylcalix [4,6,8]arene disubstituted aromatics, uracil derivatives, and estradiol epimers [39] p-tert-butylcalix [4,6,8]arene peptide bond isomers of proline [40] p-tert-butyl-calix [4]arene nucleosides, PAHs and bases [41] calix [6]<...>…”

Section: Materials and Apparatusmentioning

confidence: 99%

Preparation and Characterization of Bonded-Phases of Calixarene-Sulfonyl-Carboxamides in Partial-Cone Conformation for Determination of Salbutamol in Livestock by Nano-Mediated Bonded-Phases: Nano-Baskets of Calixarene in Partial-Cone Conformation

Bahram

Pourabdollah

2012

J. Chil. Chem. Soc.

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A new sensitive method for determination of salbutamol, as a nutrient repartitioning agent, in livestock is presented to protect the consumers. Eight nanobaskets of p-tert-calix [4]arene bearing di-[N-(X)sulfonyl carboxamide] and di-(1-propoxy) in partial-cone conformation were synthesized and were used to prepare bended phases of HPLC-UV. The new synthesized bonded-phases were characterized and optimized, the bonding interactions of solute and stationary phases were examined and the main interactions were reported. The results revealed that for the best bonded-phase, the LOD and LOQ were 0.02 and 0.06 μg/ mL, respectively.

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New calixarene-bonded stationary phases in high-performance liquid chromatography: comparative studies on the retention behavior and on influences of the eluent

Cited by 52 publications

References 30 publications

Investigation of the retention behaviour of steroids with calixarene‐based stationary phases by modern NMR spectroscopy

Investigation of the retention behaviour of steroids with calixarene‐based stationary phases by modern NMR spectroscopy

Calix[4] open‐chain crown ether‐modified, vinyl‐functionalized hybrid silica monolith for capillary electrochromatography

Preparation and Characterization of Bonded-Phases of Calixarene-Sulfonyl-Carboxamides in Partial-Cone Conformation for Determination of Salbutamol in Livestock by Nano-Mediated Bonded-Phases: Nano-Baskets of Calixarene in Partial-Cone Conformation

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