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The controlled and reversible interconversion between the free-base and thedoubly dehydrogenated form of a 5,10,15,20-tetra(p-hydroxyphenyl)porphyrinmolecule in an ordered array is demonstrated. This is achieved through voltagepulses by hydrogen transfer between the center of the porphyrin and the tip ofa scanning tunneling microscope (STM). The local dehydrogenation leads tosignificant shifts in the energetic positions of the molecular orbitals.Density functional theory (DFT) calculations corroborate our conclusions andallow to gain more insight into the different energy level alignment before andafter dehydrogenation. Due to the different conductance at a given voltage aclear distinction of both molecular species is possible, which also enables theapplication as a single-molecular switch.

Manipulation of the electronic structure by reversible dehydrogenation of tetra(p-hydroxyphenyl)porphyrin molecules