On-surface synthesis is an emerging approach to obtain, in a single step, precisely defined chemical species that cannot be obtained by other synthetic routes. The control of the electronic structure of organic/metal interfaces is crucial for defining the performance of many optoelectronic devices. A facile on-surface chemistry route has now been used to synthesize the strong electron-acceptor organic molecule quinoneazine directly on a Cu(110) surface, via thermally activated covalent coupling of para-aminophenol precursors. The mechanism is described using a combination of in situ surface characterization techniques and theoretical methods. Owing to a strong surface-molecule interaction, the quinoneazine molecule accommodates 1.2 electrons at its carbonyl ends, inducing an intramolecular charge redistribution and leading to partial conjugation of the rings, conferring azo-character at the nitrogen sites.

Centre for Mechanical Technology and Automation University of Aveiro 3810 193 Aveiro Portugal

ESISNA Group Materials Science Factory Institute of Materials Science of Madrid Sor Juana Inés de la Cruz 3 28049 Madrid Spain

Institute of Physics Academy of Sciences of the Czech Republic Cukrovarnicka 10 1862 53 Prague Czech Republic

Laboratorio TASC CNR IOM Basovizza SS 14 Km 163 5 34149 Trieste Italy

Polymer Physics Group Institute of Polymer Science and Technology Juan de la Cierva 3 28006 Madrid Spain

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