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

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.