Issue 18, 2021

Expanded all-phenylene molecular spoked wheels: cutouts of graphenylene-3

Abstract

All-phenylene molecular spoked wheels, cutouts of graphenylene-3, have been synthesized by intramolecular Yamamoto coupling of the respective dodecabromides. The uneven number of aromatics at the sides of the wheels requires a non-D6h symmetric precursor that is available via Vollhardt trimerization of an unsymmetrically substituted acetylene. The coupling gives a considerably lower yield. This is attributable to a supramolecular aggregation of the ring precursors during the coupling process that gives rise to an intermolecular dimer and oligomer formation. Larger side groups allow us to diminish this problem to a certain extent and increase the wheel yield. Scanning tunneling microscopy investigations clearly reveal the structures of the compounds with submolecular resolution and reflect the aggregation behavior. Time-resolved photoluminescence spectroscopy shows that there is no energy transfer from the rim to the spokes of the wheels due to an interruption of the conjugation at the center of the molecules.

Graphical abstract: Expanded all-phenylene molecular spoked wheels: cutouts of graphenylene-3

Supplementary files

Article information

Article type
Research Article
Submitted
10 iyn 2021
Accepted
23 iyn 2021
First published
28 iyn 2021

Org. Chem. Front., 2021,8, 4980-4985

Expanded all-phenylene molecular spoked wheels: cutouts of graphenylene-3

C. Sterzenbach, T. J. Keller, D. Kraus, J. M. Lupton, Stefan-S. Jester and S. Höger, Org. Chem. Front., 2021, 8, 4980 DOI: 10.1039/D1QO00876E

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