Cyclodextrin Porous Liquid Materials for Efficient Chiral Recognition and Separation of Nucleosides

Abstract

Porous liquids are porous materials that have exhibited unique properties in various fields. Herein, we developed a method to synthesize the type I porous liquids via liquefaction of cyclodextrins by chemical modification. The cyclodextrin porous liquids were characterized by Fourier-transform infrared (FTIR) spectroscopy, NMR, matrix-assisted laser desorption ionization-time-of-flight mass spectrometry (MALDI-TOF MS), circular dichroism (CD), and UV−vis spectroscopy. The measured ionic conductivity of the γ-cyclodextrin porous liquid was 500 times as great as that of its reactants, which was found to be the first instance with such great conductivity for a type I porous liquid. What is more, the γ-cyclodextrin porous liquid had been demonstrated experimentally to have outstanding chiral recognition ability toward pyrimidine nucleosides in water, which was further confirmed by computational simulations. Additionally, enantiomeric excess of the extracted nucleoside was achieved up to 84.81% by convenient extraction from the mixture of racemic nucleosides and γcyclodextrin porous liquid. The great features of the novel cyclodextrin porous liquids could bring opportunities in many fields, including the preparation of chiral separation materials, development of new drug screening mechanisms, and construction of chiral response materials.

Shining Light on Porous Liquids: From Fundamentals to Syntheses, Applications and Future Challenges

“…Before this, the previous review from Dai et al has stated that PLs can be used as a platform for novel chromatography columns. [17] This has been verified by the recent study of Wang et al [57] (Figure 24a,b). In this work, through liquefaction of cyclodextrins by chemical modification, a Type I PL was successfully prepared toward pyrimidine nucleosides separation in water.…”

“…Therefore, a homogeneous and stable UiO-66-OH PL with superior flowing ability at room temperature was obtained. In another study, Wang et al [57] prepared a Type 1 cyclodextrin PL via liquefaction of cyclodextrins (Figure 14b). In this paper, the cyclodextrins-based (α-CD, β-CD, and γ-CD) PLs were prepared via the reaction of imidazole-1-acetic chloride with γ-cyclodextrin in the presence of triethylamine.…”

“…[273][274][275][276][277] Toward this end, our group has prepared various nanoparticle ionic materials (NIMs) as novel nanofiller phases to enhance the damping property of polymer-based composites, such as including carbon nanotubes (CNTs)-based NIMs, graphene oxide (GO) based NIMs, (Reproduced with permission. [57] Copyright 2020, American Chemical Society). b) Left) Intermolecular interactions between γ-cyclodextrin PL and nucleosides in the lowest energy conformations by the IGM method.…”

“…(Reproduced with permission. [57] Copyright 2020, American Chemical Society). Right) Photos of as-prepared γ-cyclodextrin PL.…”

Type II porous ionic liquid based on metal-organic cage that enables L-tryptophan identification

“…Porous liquids consisting of molecular cages thereby exhibit host-guest properties, as exempli ed by the shape and size selectivity for a series of isomeric alcohols in Type I porous ionic liquids composed of tetrahedral coordination cage 4 . Most recently, Xia et al reported the use of the cyclodextrin-derived Type-I porous liquid for the e cient chiral recognition and separation of nucleosides in the solution 36 . Except for the two examples above, current research on the host-guest properties of the molecular cage-based porous liquids has been mainly focused on the accommodation of small gaseous molecules such as carbon dioxide 8,37,38 , methane 11,14,39 and chloro uorocarbon 4 .…”