Journal
MATERIALS ADVANCES
Volume 4, Issue 22, Pages 5564-5572Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3ma00698k
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This article presents an easy and reliable method to functionalize pillar[n]arene macrocycles through electrostatic interactions. The resulting ionic pillar[n]arenes self-organize into liquid crystal phases with good proton-conducting properties and exhibit interesting encapsulation properties. Moreover, the presence of coumarin moieties in the chemical structure allows for light-responsive properties and photo-induced release of encapsulated molecules.
Liquid crystal (LC) pillar[n]arenes have been barely explored due to their time-consuming and complicated synthesis, despite their promising properties for metal-ion separation, drug delivery, or surface functionalization. Herein, we report an easy and reliable method to functionalize pillar[n]arene macrocycles through electrostatic interactions. These ionic materials were prepared by ionically functionalizing a pillar[n]arene containing ten amine terminal groups with six different carboxylic acids. This supramolecular approach results in ionic pillar[n]arenes which self-organize into LC phases with good proton-conducting properties. Moreover, ionic functionalization provides a new amphiphilic character to the pillar[n]arenes, which self-assemble in water to produce a variety of nanoobjects (i.e., spherical or cylindrical micelles, vesicles, solid nanospheres, or nanotubes) that are capable of encapsulating a model hydrophobic drug. Interestingly, the presence of coumarin moieties in the chemical structure of the ionic pillar[n]arenes results in self-organized materials with light-responsive properties due to the ability of coumarins to undergo photo-induced [2+2] cycloaddition. In particular, we demonstrate that coumarin pohotodimerization can be employed to fabricate mechanically stable proton-conductive LC materials, as well as to obtain photo-responsive nanocarriers with light-induced release of encapsulated molecules. An easy and fast method to functionalize pillararenes through ionic bonds to obtain interesting materials for their encapsulation properties and proton conduction.
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