Here, we demonstrate a bottom-up synthesis of three novel nanographenes (1−3) with well-defined defects in which seven-five-seven (7−5−7)-membered rings were introduced to their sp2 carbon frameworks. From the X-ray crystallographic analysis, compound 1adopts a nearly planar structure. Compound 2, with an additional five-membered ring compared to 1, possesses a slightly saddle-shaped geometry. Compound 3, which can be regarded as the “head-to-head” fusion of 1 with two bonds, features two saddles connected together. Detailed experimental and theoretical investigations elucidate that these three nanographenes 1−3 exhibit an anti-aromatic character in their ground states and display a high stability under ambient conditions, which contrast with the reported unstable biradicaloid nanographenes that contain heptagons. Our work reported herein offers insights into the understanding of structure-related properties and enables the control of the electronic structures of expanded nanographenes with atomically precise defects.

Defective Nanographenes Containing Seven-Five-Seven (7−5−7)-Membered Rings

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