New Class of Metal Bound Molecular Switches Involving H-Tautomerism

Citations Over TimeTop 10% of 2014 papers

Abstract

A potential end-point in the miniaturization of electronic devices lies in the field of molecular electronics, where molecules perform the function of single components. To date, hydrogen tautomerism in unimolecular switches has been restricted to the central macrocycle of porphyrin-type molecules. The present work reveals how H-tautomerism is the mechanism for switching in substituted quinone derivatives, a novel class of molecules with a different chemical structure. We hence reveal that the previous restrictions applying to tautomeric molecular switches bound to a surface are not valid in general. The activation energy of switching in a prototypical quinone derivative is determined using inelastic electron tunneling. Through computational modeling, we show that the mechanism underlying this process is tautomerization of protons belonging to two amino groups. This switching property is retained upon functionalization by the addition of side groups, meaning that the switch can be chemically modified to fit specific applications.

Related Papers

• → One molecule, two states: Single molecular switch on metallic electrodes(2020)21 cited
• → The Tautomerism of Heterocycles: Substituent Tautomerism of Six-Membered Ring Heterocycles(2006)58 cited
• → Tautomeric behavior of 1,2,4-triazole derivatives: combined spectroscopic and theoretical study(2022)9 cited
• → Tautomerism in 4‐substituted 1‐phenyl‐3‐methyl‐pyrazolin‐5‐ones—a theoretical ab initio and 13C NMR study(2001)32 cited
• → Study of the Tautomerism by Experimentally and Theoretically Estimated 13 C and 15 N Chemical Shifts(1997)8 cited