Pancake bonding has recently come back into focus due to unique structural and physical properties of such systems. Pancake bonds occur through conjugated organic radicals which display highly overlapping π-stacks resulting from the energy lowering of the singly occupied molecular orbitals (SOMOs). Specific structural characteristics such as intermolecular contacts shorter than van der Waals (vdW) radii, atom over atom configurations, and slight deviations in planarity are consistently observed. Physical properties, such as tunable conductivity and magnetism, arise from the formation of the propagating π-stacked columns which provide pathways for electron transport. For these reasons, we have set to explore the formation of pancake bonded compounds with various fragments of planar nanographene through one electron oxidation, using a broad set of oxidants. As a result, several singly-oxidized compounds have been isolated and characterized, revealing formation of infinite π-stacked nanographenes, such as pyrene and others, held between respective counter anions. X-ray crystallographic studies of these compounds reveal the unique structural characteristics consistent with pancake bonded compounds, with interplanar distances shorter than vdW radii (3.4 Å), atom over atom configurations, and minor losses of planarity.

Oxidation and complexation of nanographene fragments: The pursuit of pancake bonded compounds

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ACS Fall 2022

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