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Antiaromatic and open-shell molecules are attractive because of their distinct electronic and magnetic behaviour. However, their increased reactivity creates a challenge for probing their properties. Here, we describe the on-surface and in-solution generation and characterisation of a highly reactive antiaromatic molecule: indeno[1,2- b ]fluorene ( IF ). In solution, we generated  IF  by KI-induced dehalogenation of a dibromo-substituted precursor molecule and found that  IF  survives for minutes at ambient conditions. Using atom manipulation at low temperatures we generated  IF  on Cu(111) and on bilayer NaCl. On these surfaces, we characterised  IF  by bond-order analysis using non-contact atomic force microscopy with CO-functionalised tips and by orbital imaging using scanning tunnelling microscopy. We found that the closed-shell configuration and antiaromatic character predicted for gas-phase  IF  are preserved on the NaCl film. On Cu(111), we observed significant bond-order reorganisation within the  s -indacene moiety because of chemisorption, highlighting the importance of molecule surface interactions on the  π -electron distribution.

Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces