Issue 27, 2021

Nanopatterns of molecular spoked wheels as giant homologues of benzene tricarboxylic acids

Abstract

Molecular spoked wheels with D3h and Cs symmetry are synthesized by Vollhardt trimerization of C2v-symmetric dumbbell structures with central acetylene units and subsequent intramolecular ring closure. Scanning tunneling microscopy of the D3h-symmetric species at the solid/liquid interface on graphite reveals triporous chiral honeycomb nanopatterns in which the alkoxy side chains dominate the packing over the carboxylic acid groups, which remain unpaired. In contrast, Cs-symmetric isomers partially allow for pairing of the carboxylic acids, which therefore act as a probe for the reduced alkoxy chain nanopattern stabilization. This observation also reflects the adsorbate substrate symmetry mismatch, which leads to an increase of nanopattern complexity and unexpected templating of alkoxy side chains along the graphite armchair directions. State-of-the-art GFN-FF calculations confirm the overall structure of this packing and attribute the unusual side-chain orientation to a steric constraint in a confined environment. These calculations go far beyond conventional simple space-filling models and are therefore particularly suitable for this special case of molecular packing.

Graphical abstract: Nanopatterns of molecular spoked wheels as giant homologues of benzene tricarboxylic acids

Supplementary files

Article information

Article type
Edge Article
Submitted
08 Mar 2021
Accepted
08 Jun 2021
First published
09 Jun 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 9352-9358

Nanopatterns of molecular spoked wheels as giant homologues of benzene tricarboxylic acids

T. J. Keller, C. Sterzenbach, J. Bahr, T. L. Schneiders, M. Bursch, J. Kohn, T. Eder, J. M. Lupton, S. Grimme, S. Höger and Stefan-S. Jester, Chem. Sci., 2021, 12, 9352 DOI: 10.1039/D1SC01381E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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