Aggregation Mode, Host-Guest Chemistry in Water, and Extraction Capability of an Uncharged, Water-Soluble, Liquid Pillar[5]arene Derivative

Inbar Horin, Ori Shalev, Yoram Cohen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

An uncharged, water-soluble per-ethylene-glycol pillar[5]arene derivative (1) was synthesized and its aggregation mode, host-guest chemistry in water and extraction ability was explored. Compound 1 is a liquid at room temperature; in water, limited self-aggregation occurred at high concentrations as deduced from diffusion NMR and dynamic light scattering. Compound 1 forms pseudo-rotaxane-like 1 : 1 host-guest complexes with 1,ω-di-substituted alkanes with association constants on the order of 103–104 m−1. Interestingly, NMR experiments showed that the guest location relative to the host ring system differs among the different complexes. In proof-of-concept experiments, compound 1 was shown to extract structurally related organic compounds from benzene into water with significant selectivity. Compound 1, which is a liquid at room temperature and has only limited interactions with its side arms, can, in principle, be regarded as a complement to or as a kind of type I porous liquid.

Original languageEnglish
Pages (from-to)1111-1115
Number of pages5
JournalChemistryOpen
Volume10
Issue number11
DOIs
StatePublished - Nov 2021

Keywords

  • extraction
  • host-guest complexes
  • liquid host
  • pillar[5]arene
  • water-soluble

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