Sarkar, SuchetanaÁlvarez, BertaHo Au-Yeung, KwanCobas Martínez, AgustínRobles, RobertoLorente, NicolásPeña Gil, DiegoPérez Meirás, María DoloresMoresco, Francesca2024-11-122024-11-122024-07-20S. Sarkar, B. Álvarez, K. Ho Au-Yeung, A. Cobas, R. Robles, N. Lorente, D. Peña, D. Pérez, F. Moresco, Chem. Eur. J. 2024, 30, e202402297. https://doi.org/10.1002/chem.202402297https://hdl.handle.net/10347/37673The on-surface synthesis of an isomer of undecacene, bearing two four-membered rings and two para-quinodimethane moieties, starting from a tetramethyl-substituted diepoxy precursor, is presented. The transformation implies a thermal double deoxygenation followed by a stepwise double dehydrogenation reaction on the Au(111) surface, locally induced by inelastic tunneling electrons. This results in the transformation of para-dimethylbenzene moieties into non-aromatic para-quinodimethanes. The structures and electronic properties of the intermediate and final products are investigated at the single molecule level with high spatial resolution, using both scanning tunneling microscopy/spectroscopy and non-contact atomic force microscopy. The experimental results are supported by density functional theory calculations.eng© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbHhttp://creativecommons.org/licenses/by-nc-nd/4.0/On-Surface SynthesisUndecacene isomerPara-quinodimethane moietiesInvestigaciónjournal article10.1002/chem.2024022971521-3765open access