Calixarenes as Stationary Phases in High Performance Liquid Chromatography

Śliwka-Kaszyńska, Magdalena

doi:10.1080/10408340701244672

Cited by 35 publications

(28 citation statements)

References 83 publications

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“…The host -guest interactions of calixarenes with solutes are not determined solely by their hydrophobic cavities but also by additional functional groups attached at their rims, which can contribute to potential variations in these interactions. Several functionalized calixarenes have been utilized as selectors in LC [2,3]. The modifications to these macrocycles include conformations in which the calixarene molecules are blocked, the type of functional groups and substituents present at their upper and lower rims, the calixarene ring-size, and the type of spacer fixing the macrocycles to the solid support.…”

Section: Introductionmentioning

confidence: 99%

1,3‐Alternate calix[4]arene‐bonded silica stationary phases. Effect of calixarene skeleton substituents on the retention mechanism and column selectivity

Śliwka-Kaszyńska

Jaszcolt

Anusiewicz

2009

J of Separation Science

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Four novel 1,3-alternate calix[4]arene-bonded silica gel stationary phases possessing different aromatic and aliphatic substituents at the upper rim (CalixNph, CalixBph, CalixHex, and CalixDdc) were prepared and structurally characterized. The comparison and selectivity of these phases were done by using alkylbenzenes, fatty acid p-bromophenacyl esters, aromatic positional isomers, and polynuclear aromatic hydrocarbons as analytes. Quantum chemistry calculations have also been performed (using an ab initio method) to support the experimental findings. The effect of the type and content of organic modifier on the retention and selectivity of the alkylbenzenes was studied. The retention mechanism is also discussed. The results indicate that the stationary phases behave like RP packings. However, inclusion complex formation and hydrophobic and pi-pi interactions seem to be involved in the separation process.

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Section: Introductionmentioning

confidence: 99%

1,3‐Alternate calix[4]arene‐bonded silica stationary phases. Effect of calixarene skeleton substituents on the retention mechanism and column selectivity

Śliwka-Kaszyńska

Jaszcolt

Anusiewicz

2009

J of Separation Science

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“…The host-guest interactions of calixarenes with solutes are not determined solely by their hydrophobic cavities, but are also influenced by additional functional groups attached at their rims, which can contribute to potential variations in these interactions. Several functionalized calixarenes were utilized as selectors in liquid chromatography [3,4]. Modifications of these macrocycles comprised: conformations in which calixarene molecules are blocked; different types of functional groups and substituents present at their upper and lower rim; changes in the calixarene ring-size; and, finally, different types of spacer fixing macrocycles to the stationary phases.…”

Section: Introductionmentioning

confidence: 99%

“…Modifications of these macrocycles comprised: conformations in which calixarene molecules are blocked; different types of functional groups and substituents present at their upper and lower rim; changes in the calixarene ring-size; and, finally, different types of spacer fixing macrocycles to the stationary phases. Calix[n]arenes (n = 4,6,8) in cone conformation functionalized at the upper rim by tert-butyl substituents and permanently attached to solid support attracted great attention. However, some examples of calixarenes functionalized with other substituents, including chiral residues, were also successfully used as selectors in HPLC separations [5,6].…”

Section: Introductionmentioning

confidence: 99%

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Preparation and HPLC evaluation of a new 1,3‐alternate 25,27‐bis‐[p‐chlorobenzyloxy]‐26,28‐bis‐[3‐propyloxy]‐calix[4]arene silica bonded stationary phase

Śliwka-Kaszyńska

Karaszewski

2008

J of Separation Science

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The 1,3-alternate 25,27-bis-[p-chlorobenzyloxy]-26,28-bis-[3-propyloxy]-calix[4]arene-bonded silica gel stationary phase was synthesized, structurally characterized, and used as a selector in high performance liquid chromatography. Selectivity studies on that phase used aromatic positional isomers, alkylbenzenes, polynuclear aromatic hydrocarbons, sulfonamides, and non-steroidal anti-inflammatory drugs as analytes. The effects of organic modifier content and pH of the mobile phase on retention and selectivity of selected aromatic positional isomers were studied. Selectivity comparisons of the novel phase vs. 1,3-alternate 25,27-di-[benzyloxy]-26,28-bis-[3-propyloxy]-calix[4]arene phase and commercially available RP-Phenyl phases were performed. The retention mechanism was also discussed. The results indicated that the calixarene stationary phase behaves like a reversed-phase packing; however, other retention mechanisms seem to be involved in the separation process.

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“…These molecules have been used in a wide range of applications including chromatography and sensors [2,3]. The butyl and pentyl substituated structures have been reported [4,5].…”

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Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C₆₈H₁₀₄O₄

Patel

Samipillai

Friedrich

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1533990The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. to dimethyl sulfoxide (25 mL). The reaction mixture was warmed to 50°C. 1-Bromohexane (1.23 mmol, 0.203 g) was added and the mixture was stirred for 6 h at 70-75°C. After cooling to 20°C the reaction mixture was poured into dilute hydrochloric acid. The precipitate was dried and recrystallized from acetonitrile (0.14 g, 70%). m.p. 394-396 K. Crystals were grown at room temperature from acetone:acetonitrile (3:1). Experimental detailsAnisotropical displacement parameters for certain atoms were constrained. Certain carbon atoms were disordered over two positions and their site occupancy factors were refined. All hydrogen atoms were placed in idealised positions and refined in riding models with U iso assigned 1.2 or 1.5 times Ueq of their parent atoms and the bond distances were constrained to 0.95 Å, 0.98 Å or 0.99 Å. DiscussionThe title compound was first synthesised by Kenis et al. [1]. The tetraether compound belongs to the family of calixarenes.

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Calixarenes as Stationary Phases in High Performance Liquid Chromatography

Cited by 35 publications

References 83 publications

1,3‐Alternate calix[4]arene‐bonded silica stationary phases. Effect of calixarene skeleton substituents on the retention mechanism and column selectivity

1,3‐Alternate calix[4]arene‐bonded silica stationary phases. Effect of calixarene skeleton substituents on the retention mechanism and column selectivity

Preparation and HPLC evaluation of a new 1,3‐alternate 25,27‐bis‐[p‐chlorobenzyloxy]‐26,28‐bis‐[3‐propyloxy]‐calix[4]arene silica bonded stationary phase

Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C₆₈H₁₀₄O₄

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Calixarenes as Stationary Phases in High Performance Liquid Chromatography

Cited by 35 publications

References 83 publications

1,3‐Alternate calix[4]arene‐bonded silica stationary phases. Effect of calixarene skeleton substituents on the retention mechanism and column selectivity

1,3‐Alternate calix[4]arene‐bonded silica stationary phases. Effect of calixarene skeleton substituents on the retention mechanism and column selectivity

Preparation and HPLC evaluation of a new 1,3‐alternate 25,27‐bis‐[p‐chlorobenzyloxy]‐26,28‐bis‐[3‐propyloxy]‐calix[4]arene silica bonded stationary phase

Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C68H104O4

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Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C₆₈H₁₀₄O₄