Self-assembly of supra-amphiphiles building block fabricated by β-cyclodextrin and adamantane-based ionic liquid

Abstract

A new adamantane-based ionic liquid, (11-(((-adamantane-1-carbonyl)oxy)undecyl)-1-methylimidazol-3-ium bromide (AD-C 11 im), was synthesized from 1-adamantanecarboxylic acid and observed that it can aggregate into micelles in aqueous solution. A number of experiments were conducted to understand the self-assembly of supra-amphiphiles building block fabricated by b-cyclodextrin (b-CD) and adamantane-based ionic liquid at diverse molar ratios. Studies revealed that host-guest interaction between the adamantane group and b-CD occurred and AD-C 11 im@1b-CD building block formed when same amount b-CD was added. Then the micelles aggregates formed by AD-C 11 im only turned into spherical vesicles, which was confirmed by AFM, DLS and TEM.Besides, according to the results of AFM, it can be confirmed that the vesicles were monolayer structure. When double amount b-CD was added, both the adamantane group and the hydrophobic chain were encapsulated by b-CD and AD-C 11 im@2b-CD building block formed. Thus the aggregations changed from vesicles to net-like nanofiber, which was observed by TEM. When the b-CD concentration increased to 40 mM, the formation of light blue hydrogel was observed during the self-assembling process of AD-C 11 im@2b-CD building block.

Roles of Ionic Liquids in Adjusting Nature of Ionogels: A Mini Review

“…Zhong et al. [ 42 ] also introduced an adamantane‐based ionogel based on the host–guest interaction between β‐CD and with adamantane group. Except for cyclodextrin molecule, Ma et al.…”

“…This ionogel contains β-CD and an asymmetric Gemini ZIL which contains azobenzene and bis(trifluoromethanesulfonyl)imide (TFSI − ), the host-guest interaction between β-CD with photoresponsive azobenzene group and TFSI − ion can be control by regulating the photon radiation and temperature. Zhong et al [42] also introduced an adamantanebased ionogel based on the host-guest interaction between β-CD and with adamantane group. Except for cyclodextrin molecule, Ma et al [43] reported an ionogel with detectability to CO 2 based on host-guest interaction between a carbamate IL guest molecule with a bis-cyanostilbene derivative host molecule (Figure 3B).…”

Adsorptive removal of uranium(vi) from wastewater using a crosslinked amidoxime-functionalized β-cyclodextrin polymer

“…Hence, it has a hydrophobic inner cavity and a hydrophilic outer surface. 18 As a natural product, it is cheap, non-toxic, has good biocompatibility and excellent biodegradability and is easy to modify due to a large number of hydroxyl groups on its surface. In particular, its inner cavity can form inclusion complexes with specific pollutant molecules, so it has attracted a great deal of attention in the removal of pollutants from wastewater.…”

Ionic Liquid−β-Cyclodextrin Vesicle-Based Mechanochemical-Assisted Extraction for the Weak Acid Compounds from Mori Fructus

“…For example, Zhong et al found spherical vesicles AD-C 11 im@1β-CD formed when the amount of β-CD was added the same as 11-(((-adamantane-1carbonyl)oxy)undecyl)-1-methylimidazol-3-iumbromide (AD-C 11 im), which was also confirmed by atomic force microscopy (AFM), dynamic light scattering (DLS), and transmission electron microscopy (TEM). 22 Shi et al discovered the formation of vesicles in the concentrated aqueous solution of 1-dodecyl-3-methylimidazolium bromide (C 12 mimBr) and β-CD and thought that it was the H-bonding between β-CD and water, β-CDs, as well as the imidazolium headgroup of C 12 mim + and water that contribute to the C 12 mimBr@β-CD selfassembly vesicle system. 23 However, as far as we know, there have never been studies on the applications of ionic liquid@β-CD vesicles in the extraction fields.…”