Issue 2, 2023

Tautomerization of single asymmetric oxahemiporphycene molecules on Cu(111)

Abstract

We have studied 22-oxahemiporphycene molecules by a combination of scanning tunneling microscopy at low temperatures and density functional theory calculations. In contrast to other molecular switches with typically two switching states, these molecules can in principle exist in three different tautomers, due to their asymmetry and three inequivalent binding positions of a hydrogen atom in their macrocycle. Different tautomers are identified from the typical appearance on the surface and tunneling electrons can be used to tautomerize single molecules in a controllable way with the highest rates if the STM tip is placed close to the hydrogen binding positions in the cavity. Characteristic switching processes are explained by the different energy pathways upon adsorption on the surface. Upon applying higher bias voltages, deprotonation occurs instead of tautomerization, which becomes evident in the molecular appearance.

Graphical abstract: Tautomerization of single asymmetric oxahemiporphycene molecules on Cu(111)

Supplementary files

Article information

Article type
Paper
Submitted
11 Oct 2022
Accepted
09 Dec 2022
First published
19 Dec 2022
This article is Open Access
Creative Commons BY license

Phys. Chem. Chem. Phys., 2023,25, 1096-1104

Tautomerization of single asymmetric oxahemiporphycene molecules on Cu(111)

S. Jaekel, E. Durant, M. Schied, M. Persson, J. Ostapko, M. Kijak, J. Waluk and L. Grill, Phys. Chem. Chem. Phys., 2023, 25, 1096 DOI: 10.1039/D2CP04746B

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