Unexpected Encapsulation of Selected Polycyclic Aromatic Hydrocarbons by β-Cyclodextrin Studied Using UV-Vis Spectrophotometry, Micro-Planar Chromatography and Temperature Dependent Inclusion Chromatography

Abstract

This research communication significantly extends our previous studies focusing on the temperature effects related to the unexpected chromatographic behavior of 1-acenaphthenol in the presence of native β-cyclodextrin (β-CD) additive, working under thin-layer chromatographic (TLC) conditions. We have applied complementary and orthogonal techniques including (i) temperature-controlled ultraviolet-visible (UV-VIS) spectroscopy, (ii) thermostated microplanar high-performance chromatography (micro-HPTLC) and (iii) temperature-dependent inclusion chromatography based on high-performance liquid chromatography (HPLC) to investigate the retention behavior of related host molecules. Particularly, various symmetric and asymmetric molecules were tested, such as: naphthalene and its derivatives including acenaphthylene, acenaphthene and selected dimethynaphthalenes: 1,8-DMN, 1,5-DMN, 2,3-DMN and 2,6-DMN. Reported raw experimental data, particularly performed in liquid phase and detected by UV-Vis spectrophotometry, may suggest that solubility changes of the supramolecular complexes studied and differences in total analysis time between TLC and HPLC separation can trigger strong retention of target components in planar chromatographic systems. This was also supported by principal component analysis (PCA) of the multi-source data obtained. It is hoped that the reported analyses enable the adjustment of phenomenological models describing liquid chromatography retention and the solubility behavior of low-molecular mass guest molecules, controlled by supramolecular interactions with selected macrocycles. It should be noted that the reported phenomenon, specifically supramolecular complexes precipitation, may have a number of practical applications. This can be used to improve the efficiency and selectivity of planar and/or microfluidic systems. On the other hand, precipitation via host-guest interactions may be applied for highly selective water purification technological processes that will be designed for the removal of given organic micropollutants.