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For a molecular radical to be stable, the environment needs to be inert.Furthermore, an unpaired electron is less likely to react chemically, when itis placed in an extended orbital. Here, we use the tip of a scanning tunnelingmicroscope to abstract one of the pyrrolic hydrogen atoms from phthalocyanine(H2Pc) deposited on a single layer of molybdenum disulfide (MoS2) on Au(111).We show the successful dissociation reaction by current-induced three-levelfluctuations reflecting the inequivalent positions of the remaining H atom inthe pyrrole center. Tunneling spectroscopy reveals two narrow resonances insidethe semiconducting energy gap of MoS2 with their spatial extent resembling thehighest occupied molecular orbital (HOMO) of H2Pc. By comparison to simpledensity functional calculations of the isolated molecule, we show that thesecorrespond to a single occupation of the Coulomb-split highest molecularorbital of HPc. We conclude that the dangling $\sigma$ bond after N-H bondcleavage is filled by an electron from the delocalized HOMO. The extendednature of the HOMO together with the inert nature of the MoS2 layer favor thestabilization of this radical state.

$\pi$-Radical Formation by Pyrrolic H Abstraction of Phthalocyanine Molecules on Molybdenum Disulfide