Ionic self-assembly of pillar[5]arenes: proton-conductive liquid crystals and aqueous nanoobjects with encapsulation properties

Marín, Iván (Universidad de Zaragoza) ; Merino, Rosa I. ; Barberá, Joaquín (Universidad de Zaragoza) ; Concellón, Alberto (Universidad de Zaragoza) ; Serrano, José L. (Universidad de Zaragoza)

Resumen: 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.

Idioma: Inglés

DOI: 10.1039/d3ma00698k

Año: 2023

Publicado en: Materials Advances 4, 22 (2023), 5564-5572
ISSN: 2633-5409

Factor impacto CITESCORE: 7.6 - Chemistry (miscellaneous) (Q1) - Materials Science (all) (Q1)

Factor impacto SCIMAGO: 1.033 - Materials Science (miscellaneous) (Q1) - Chemistry (miscellaneous) (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E47-23R
Financiación: info:eu-repo/grantAgreement/ES/MICINN-FEDER/PID2021-122882NB-I00
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PGC2018-097583-I00
Financiación: info:eu-repo/grantAgreement/ES/MICINN/RYC2021-031154-I

Tipo y forma: Article (Published version)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)