On-surface synthesis has emerged as a potent tool for crafting intricate molecules and materials that prove challenging in traditional in-solution chemistry. In this work, a cyclopenta[c,d]azulene chevron-like graphene nanoribbon (GNR) has been synthesized from a cyclooctatetraene (COT) containing precursor. The on-surface COT-cyclopenta[c,d]azulene rearrangement was investigated through computational studies, unveiling a specific dependence on the curvature of the initial COT-containing polymer (concavity vs convexity). The electronic properties of the GNR showcases a bandgap shortening induced by the non-benzenoid rings in comparison to pristine chevron-GNRs. This work contributes to a deeper understanding of the stability of higher-order non-hexagonal rings and the impact of its curvature on the on-surface reactions, while paving the way for tailoring the properties of GNRs such as electronic bandgap through the introduction of non-benzenoid rings.

Resumen del trabajo presentado al On-Surface Synthesis Workshop (OSS24), celebrado en Sant Feliu de Guíxols (España) del 2 al 7 de junio de 2024.

Peer reviewed