Self-Assembly of Hollow Organic Nanotubes Driven by Arene Regioisomerism

Alegre-Requena, J.V. ; Pérez Herrera, Raquel (Universidad de Zaragoza) ; Díaz Díaz, D.

Resumen: Arene regioisomerism in low-molecular-weight gelators can be exploited as a tool to modulate the micro-structures of the corresponding xerogel networks by using the three different possible substitution patterns ortho, meta and para. This aromatic regioisomer-driven strategy has been used with a cholesterol-based gelator to prepare hollow self-assembled organic nanotubes (S-ONTs) with inside and outside diameters of ca. 35 and 140 nm, respectively. Electron microscopy imaging and theoretical calculations were employed to rationalize the formation mechanism of these S-ONTs. From the three possible regioisomers, only the ortho-disubstituted cholesteryl-based gelator showed the optimal angle and distance between substituents to afford the formation of the cyclic assemblies required for nanotube growth by assembling 30–40 units of the gelator. This study opens fascinating opportunities to expand the synthesis of controllable and unique microstructures by modulating geometrical parameters through aromatic regioisomers.

Idioma: Inglés

DOI: 10.1002/cplu.202000473

Año: 2020

Publicado en: ChemPlusChem 85, 11 (2020), 2372-2375
ISSN: 2192-6506

Factor impacto JCR: 2.863 (2020)

Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 95 / 178 = 0.534 (2020) - Q3 - T2

Factor impacto SCIMAGO: 0.801 - Chemistry (miscellaneous) (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA-FSE/E07-20R
Financiación: info:eu-repo/grantAgreement/ES/MCIU/RED2018-102471-T
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2017-88091-P

Tipo y forma: Article (Published version)

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