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

Abstract

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

arXiv comment10 pages, 6 figures

References in corpus (3)

• Reversible Photomechanical Switching of Individual Engineered Molecules at a Surface
• Manipulating Kondo Temperature via Single Molecule Switching
• Reversible Single Spin Control of Individual Magnetic Molecule by Hydrogen Atom Adsorption

Cited by in corpus (4)

• Self-Metalation of Phthalocyanine Molecules with Silver Surface Atoms by Adsorption on Ag(110)
• Interplay of hydrogen bonding and molecule-substrate interaction in self-assembled adlayer structures of a hydroxyphenyl-substituted porphyrin
• $\pi$-Radical Formation by Pyrrolic H Abstraction of Phthalocyanine Molecules on Molybdenum Disulfide
• Photoelectron spectroscopy investigation of the temperature-induced deprotonation and substrate-mediated hydrogen transfer in a hydroxyphenyl-substituted porphyrin