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Herein, we synthesized and used a novel pillar[5]arene with two functionalizable rims (AP5A-C10-OAc) as stationary phase in gas chromatography (GC). The AP5A-C10-OAc column (0.25 mm, i.d.) showed a high column efficiency of 4107 plates/m and medium polarity. The AP5A-C10-OAc stationary phase possesses unique amphiphilic structure, including a π-electron rich cavity and two functionalized arms composed of five nonpolar alkyl chains and five polar ester chains, and showed good separation performance for diverse types of analytes and isomers (apolar/polar, aliphatic/aromatic). Particularly, the AP5A-C10-OAc phase showed high selectivity for the challenging isomers of chloronitrobenzenes, bromonitrobenzenes, benzenediols, and iodoanilines with distinct advantages if compared with the commercial polysiloxane column. [ABSTRACT FROM AUTHOR]

Pillar[ n ]arenes (P[ n ]As, n = 5–10), a new generation of macrocyclic hosts, display interesting properties such as 3D π -electron cavity, host-guest interactions, good stability, and easy functionalization, which make these polymers very promising for separation applications. In particular, extended P[ n ]As (EP[ n ]As) show large-sized cavities, structural flexibility, cavity adaptability, and synthetic accessibility. These characteristics have been exploited in this work, which reports for the first time the investigation of two EP[ n ]As (LP6A-C10 and BpP6A-C10) as stationary phases for gas chromatography (GC). LP6A-C10 and BpP6A-C10 columns exhibited moderate polarity (average polarity 117 and 118) and high column efficiencies (3000 plates/m and 3235 plates/m). These columns achieved complete challenging separation of halogenated benzene, benzaldehyde, phenol, and aniline isomers, which are difficult to resolve due to their high resemblance in structures and properties. Experimental results demonstrate the high selectivity and inertness of the prepared columns and their distinct advantages if compared with commercial HP-5 and HP-35 columns. EP[ n ]As columns displayed good separation repeatability with RSD values of 0.01%–0.02 % for run-to-run, 0.01%–0.22 % for day-to-day, and 1.36–3.56 % for column-to-column. This work demonstrates the promising future of EP[ n ]A stationary phases for chromatographic separations. [Display omitted] • Extended pillar[6]arenes explored as novel stationary phases in capillary gas chromatography. • High-resolution separation of halogenated benzene, benzaldehyde, phenol and aniline isomers. • Advantageous and unmatched performances of the proposed chromatographic columns over the commercial HP-5 and HP-35 columns. [ABSTRACT FROM AUTHOR]

[Display omitted] In this work, a novel pillar[6]arene bonded with octyl-imidazolium ionic liquids (IMP6A-C4) as a stationary phase for gas chromatographic (GC) separations was designed, synthesized, and characterized. The IMP6A-C4 capillary column, prepared by the static coating method, had medium polarity (1 3 3) and relatively high column efficiency of 4982 plates/m determined by n-dodecane at 120 ℃. As demonstrated, through the separation of the mixture of 17 aliphatic analytes and the mixture of 20 analytes with different polarities, the IMP6A-C4 column exhibited privileged retention and high resolving capacity for H-bonded and aromatic analytes, suggesting advantages over the P6A-C4 column and common polysiloxane HP-5 and HP-35 columns. Strikingly, it implemented high resolutions with good peak shapes for isomer mixtures of phenols, anilines, and benzaldehydes. These findings demonstrated that the excellent resolving performance of the IMP6A-C4 column can be attributed to the comprehensive interactions of its rigid 3D aromatic cavities and polar imidazolium ionic liquids, including π-π, ion-π, H-bonding, dipole–dipole interactions. On the other hand, the IMP6A-C4 capillary column exhibited good repeatability and reproducibility with the RSD% values in the range of 0.01–0.03% for run-to-run, 0.09–0.32% for day-to-day, and 2.72–5.23% for column-to-column. The satisfactory separation performance reveals the promising prospects of the IMP6A-C4 stationary phase in separation science. [ABSTRACT FROM AUTHOR]