Abstract <p>Pillar[<i>n</i>]arenes (<i>n</i> = 5–10), novel macrocycles, are gaining prominence in supramolecular studies owing to their distinctive three-dimensional architecture featuring a π-electron-rich cavity and have emerged as a key synthetic macrocyclic host in research. Extended pillar[<i>n</i>]arenes (<b>Ep[</b><Emphasis Type="BoldItalic">n</Emphasis><b>]As</b>) notably feature sizable internal voids, adaptable structures, versatile cavity shapes, and ease of synthesis. This work presents the first example of imidazolium ionic liquid-functionalized Ep[<i>n</i>]As (BpP6A-C10-IM-C8[NTf<sub>2</sub>]) as a gas chromatography stationary phase. The BpP6A-C10-IM-C8[NTf<sub>2</sub>] column was prepared by the static method, exhibiting medium polarity and high column efficiency (4660 plates/m, <i>k</i> = 2.29). The separation performance of the prepared column was evaluated for analytes, including a mixture of 22 analytes, more than 12 positional isomers, and 8 <i>cis-</i>/<i>trans-</i>isomers. Furthermore, the chromatograms of the challenging isomers of bromonitrobenzenes, chloronitrobenzenes, bromobenzaldehydes, toluidines, and dimethylanilines on the BpP6A-C10-IM-C8[NTf<sub>2</sub>] column were compared with those on the BpP6A-C10 column and commercial HP-5 and HP-35 columns. The BpP6A-C10-IM-C8[NTf<sub>2</sub>] column also showed high selectivity for biphenyl isomers, including methylbiphenyls, iodobiphenyls, and bromobiphenyls.</p>

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Imidazolium Ionic Liquid-Functionalized Extended Pillar[6]Arene with High Selectivity for Gas-Chromatographic Separations

  • Haolong Qi,
  • Haixin Liu,
  • Xin Shen,
  • Yuanyuan Zhang,
  • Xiang Xu,
  • Kexin Yang,
  • Linyi Wei,
  • Yongrui He,
  • Tao Sun,
  • Zhiqiang Cai

摘要

Abstract

Pillar[n]arenes (n = 5–10), novel macrocycles, are gaining prominence in supramolecular studies owing to their distinctive three-dimensional architecture featuring a π-electron-rich cavity and have emerged as a key synthetic macrocyclic host in research. Extended pillar[n]arenes (Ep[n]As) notably feature sizable internal voids, adaptable structures, versatile cavity shapes, and ease of synthesis. This work presents the first example of imidazolium ionic liquid-functionalized Ep[n]As (BpP6A-C10-IM-C8[NTf2]) as a gas chromatography stationary phase. The BpP6A-C10-IM-C8[NTf2] column was prepared by the static method, exhibiting medium polarity and high column efficiency (4660 plates/m, k = 2.29). The separation performance of the prepared column was evaluated for analytes, including a mixture of 22 analytes, more than 12 positional isomers, and 8 cis-/trans-isomers. Furthermore, the chromatograms of the challenging isomers of bromonitrobenzenes, chloronitrobenzenes, bromobenzaldehydes, toluidines, and dimethylanilines on the BpP6A-C10-IM-C8[NTf2] column were compared with those on the BpP6A-C10 column and commercial HP-5 and HP-35 columns. The BpP6A-C10-IM-C8[NTf2] column also showed high selectivity for biphenyl isomers, including methylbiphenyls, iodobiphenyls, and bromobiphenyls.