ArticleJournal of the American Chemical Society2025
On-Surface Synthesis of a Nitrogen-Doped Curved Cycloarene: π-Extended Pentaazaquintulene and Its Gold Complex.
Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
The interplay between π-electron conjugation and molecular geometry has been a central focus in the development of modern hydrocarbon research. Herein, we report the on-surface synthesis and characterization of the nonplanar, π-extended, nitrogen-doped quintulene C85N5 on a Au(111) surface. The as-synthesized C85N5 adopts a convex geometry, which can be inverted to a concave geometry by single-molecule manipulation. In its convex conformation, C85N5 may coordinate a gold atom within its central pore, forming an Au-C85N5 complex through interactions with the pyridinic nitrogen atoms. The structures and electronic properties of these cycloarenes are elucidated by noncontact atomic force microscopy (nc-AFM), scanning tunneling microscopy and spectroscopy (STM/STS), and density functional theory (DFT) calculations. Our results highlight that on-surface synthesis enables the atomically precise generation of curved (hetero)nanographenes and their metal complexes. Despite the inherent challenges of the nonplanar π-system, both geometric and electronic features can be characterized in detail, and controlled manipulation by scanning probe techniques is feasible.
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