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 language | English |
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Pages (from-to) | 1111-1115 |
Number of pages | 5 |
Journal | ChemistryOpen |
Volume | 10 |
Issue number | 11 |
DOIs | |
State | Published - Nov 2021 |
Keywords
- extraction
- host-guest complexes
- liquid host
- pillar[5]arene
- water-soluble