Separation of Aromatic Isomers by Capillary Gas Chromatography with Two Calix[4]arene Polysiloxane Stationary Phases

Abstract

Two new stationary phases, cone bis(undecenyloxy)-p-t-butyl calix [4]crown-5 polysiloxanes (PSO-C-c[4]c-5) and partial cone 5,11,17,23-t-butyl-25,27-diethoxy-26,28-diundecenyl calix[4]arene polysiloxane (PSO-PC-c[4]E), are synthesized and used as stationary phases in capillary column gas chromatography. Their chromatographic characteristics, such as column efficiency, capacity factor, average polarity, operation temperature range, and peak asymmetry were measured. Their column efficiency is over 3000 plates m −1 , and their average polarities are between that of OV-1701 and SE-54. Their maximum allowable operating temperature is up to 310˚C. Then, 33 aromatic compounds and positional isomers were used to test the separation abilities of the two stationary phases. The results indicate that the synthetic calixarene stationary possess good separation ability for aromatic compounds and positional isomers. It is noticeable that the retention behavior of several positional isomers on the PSO-C-c[4]c-5 column are different from that on PSO-PC-c[4]E column. The separation mechanism is also discussed.

Syntheses and adsorption properties of novel calixarene polymers: Calix[6]-1,4-crown-4-based netty polymers

“…As calixcrowns possess well-preorganized structures and more rigid binding sites in comparison with calixarenes and crown ethers, they exhibited superior recognition ability, specially, the complexation selectivity toward cations [1,2]. With the extensive and in-depth studies of all kinds of calixcrowns, more and more attentions are paid to calixcrown-based polymers which may be processed into materials with potential applied perspective on ion exchange and adsorption [3], gas chromatogram [4], ion chromatogram [5], etc.…”

“…In 1995, Zhong et al [6] first reported the synthesis and properties of the calix [4]crown sioxane polymer. Arena reported the utility of calix [4] silica gel for the separation of Na + and Cs + in liquid chromatography [7].…”

“…Arena reported the utility of calix [4] silica gel for the separation of Na + and Cs + in liquid chromatography [7]. Kim et al [8] observed that the binding abilities of calix [4]crown telomers toward alkali metal and selected transition metal ions are higher than that of monomeric analogue. Yilmaz et al [9][10][11] reported a series of calix [4]crown-based polymers as well as their excellent complexation capabilities.…”

Bausteine mit Hohlräumen in supramolekularen Gelen

“…[39] In Kieselgel eingeschlossene Cavitanden wurden für Umweltüberwachung [40] und Chromatographie eingesetzt. [41] In den frühen 90er Jahren haben Shinkai und Mitarbeiter [42,43] [45][46][47] wird eine Vielzahl von möglichen Wirt-Gast-Elementen für solche supramolekularen Polymere aufgezeigt (Abbildung 1).…”

Study of the gas chromatographic properties of calix[4]arene derivatives containing different substituents on the upper rim

“…Since calixarene has a special cavity structure, high melting point and thermal stability, it was found to be useful in gas chromatography (GC) as stationary phase. Mangia et al [2] first reported in 1983 the separation of homologues of alcohol, chlorinated hydrocarbons and aromatics on a column packed with calix [8]arene supported on silanized Chromosorb W. Feltl et al [3,4] further reported the inclusion properties of unsubstituted calixarenes in gas chromatography, but, as the result of low column efficiency, their utility in GC is limited. Our group have synthesized several lowerrim modified calix [4]arene derivatives and evaluated their gas chromatographic properties.…”