Sterzenbach, Christopher and Keller, Tristan J. and Kraus, Daniel and Lupton, John M. and Jester, Stefan-S. and Hoeger, Sigurd (2021) Expanded all-phenylene molecular spoked wheels: cutouts of graphenylene-3. ORGANIC CHEMISTRY FRONTIERS, 8 (18). pp. 4980-4985. ISSN 2052-4129
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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-D-6h 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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | SYSTEMS |
| Subjects: | 500 Science > 530 Physics |
| Divisions: | Physics > Institute of Experimental and Applied Physics > Chair Professor Lupton > Group John Lupton |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 23 Aug 2022 11:29 |
| Last Modified: | 23 Aug 2022 11:29 |
| URI: | https://pred.uni-regensburg.de/id/eprint/46849 |
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