Synthesis of a Negatively Curved Nanocarbon Molecule with an Octagonal Omphalos via Design‐of‐Experiments Optimizations Supplemented by Machine Learning

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A saddle-shaped nanocarbon molecule was synthesized, which revealed the existence of negative Gauss curvatures on a >3-nm molecular structure possessing 192 π-electrons. The synthesis was facilitated by a protocol developed with Design-of-Experiments optimizations and machine-learning predictions, and spectroscopy and crystallography were used to reveal the saddle-shaped structure of the molecule. Solution-phase analyses showed the presence of dimeric assembly, and crystallographic analyses revealed the stacked dimeric structures. The stacked crystal structure was scrutinized by various methods, including Gauss curvatures derived from the discrete surface theory of geometry, to reveal the important role of the molecular Gauss curvature in dimeric assembly.