Open AccessAggregation Mode, Host‐Guest Chemistry in Water, and Extraction Capability of an Uncharged, Water‐Soluble, Liquid Pillar[5]arene Derivative
Author(s) -
Horin Inbar,
Shalev Ori,
Cohen Yoram
Publication year - 2021
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.202100206
Subject(s) - chemistry , derivative (finance) , extraction (chemistry) , benzene , host–guest chemistry , ethylene glycol , liquid–liquid extraction , dynamic light scattering , pillar , organic chemistry , chemical engineering , molecule , supramolecular chemistry , structural engineering , nanoparticle , financial economics , engineering , economics
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 10 3 –10 4 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.