Self-Assembly of Hollow Organic Nanotubes Driven by Arene Regioisomerism

Alegre-Requena, Juan and Herrera, Raquel P. and Diaz Diaz, David (2020) Self-Assembly of Hollow Organic Nanotubes Driven by Arene Regioisomerism. CHEMPLUSCHEM, 85 (11). pp. 2372-2375. ISSN 2192-6506,

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Abstract

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 patternsortho,metaandpara. 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 theortho-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.

Item Type: Article
Uncontrolled Keywords: SOL-GEL TRANSCRIPTION; BASIS-SETS; HELICAL RIBBON; TEMPLATE; ORGANOGEL; CREATION; OPTIMIZATION; DERIVATIVES; SOLVENTS; gels; nanotubes; regioisomers; self-assembly; supramolecular chemistry
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie
Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. David Díaz Díaz
Depositing User: Dr. Gernot Deinzer
Date Deposited: 16 Mar 2021 07:30
Last Modified: 16 Mar 2021 07:30
URI: https://pred.uni-regensburg.de/id/eprint/44006

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