Ionic bent-core pillar[n]arenes: from liquid crystals to nanoaggregates and functional applications

Marín, Iván ; Castillo-Vallés, Martín ; Merino, Rosa I. ; Folcia, César L. ; Barberá, Joaquín (Universidad de Zaragoza) ; Ros, M. Blanca (Universidad de Zaragoza) ; Serrano, José L. (Universidad de Zaragoza)

Resumen: Herein, we report the first examples of supramolecular systems from bent-core-based pillar[n]arenes through ionic bonds. These ionic materials have been prepared by the interaction of an amino-ended pillar[5]arene (P5N10) and three different carboxylic acids, including bent-core moieties. The bent-core units are based on ester, biphenyl, and azobenzene structures bearing two different flexible spacers between the carboxyl group and the central bent-core aromatic units. The ionic pairs segregate the molecular blocks, leading to columnar liquid crystal organizations. These ionic supramolecular compounds exhibit interesting results as proton-conductive materials. Furthermore, the introduction of azobenzene units in the bent-core structure has provided a photoresponse to the proton conduction materials. Interestingly, the amphiphilic character generated by the ionic pairs and the hydrophobic bent-core structures allows their molecular self-assembly in water solution, resulting in aggregates of appealing morphologies. The structural modifications of the bent-core units (i.e., connecting bonds at the lateral structure and spacer lengths) provide an attractive analysis on the relationship between the chemical structure and the morphology of the aggregates (fibers, chiral ribbons, nanotubes...). Additionally, the self-assembly process and evolution of the aggregates from fibers to nanotubes have been studied with several techniques.

Idioma: Inglés

DOI: 10.1021/acs.chemmater.4c01952

Año: 2024

Publicado en: Chemistry of materials 36, 19 (2024), 9793-9805
ISSN: 0897-4756

Financiación: info:eu-repo/grantAgreement/ES/DGA/E47-23R
Financiación: info:eu-repo/grantAgreement/ES/DGA/T02-23R
Financiación: info:eu-repo/grantAgreement/ES/MICINN-FEDER/PID2021-122882NB-I00
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PID2023-150255NB-I00

Tipo y forma: Article (Published version)

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