Polycyclic aromatic hydrocarbons as test probes to investigate the retention behavior of 1,3‐alternate calix[4]arene silica‐bonded stationary phases |
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Authors: | Magdalena Śliwka‐Kaszyńska Marek Ślebioda |
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Affiliation: | 1. Department of Organic Chemistry, Gdansk University of Technology, Gdańsk, Poland;2. Perlan Technologies Sp. z.o.o., Warszawa, Poland |
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Abstract: | A series of polycyclic aromatic hydrocarbons (PAHs) of different size and shape has been used to characterize the chromatographic behavior of five calix[4]arene stationary phases in 1,3‐alternate conformation synthesized in our laboratory. The selection of linear, four‐ring nonlinear, and five‐ring PAHs gave data on selectivity changes across range of the calix[4]arene columns. Retention of the 12 aromatic solutes has been evaluated at various methanol contents in the mobile phase (70–100% v/v) and column temperatures (20–45°C). The thermodynamic parameters underlying the retention mechanisms revealed that each of the five calix[4]arene columns exhibited variation in selectivity and retention of PAHs caused by enthalpy and entropy effects. The calixarene stationary phases substituted with electron‐withdrawing groups exhibit enhanced selectivity toward PAHs in comparison to the rest of the investigated columns. The observed divergences are due to differences in solute–stationary phase interactions and originate in π–π and π‐electron transfer specific to the analytes and the type of calix[4]arene functionalization at the upper rim, as well as steric and sorption phenomena. |
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Keywords: | Calix[4]arene stationary phases Column characterization Polycyclic aromatic hydrocarbons Retention behavior Thermodynamics |
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