New class of metal bound molecular switches involving H-tautomerism

Grant James Simpson, Simon William Leslie Hogan, Marco Caffio, Christopher J. Adams, Herbert Anton Fruchtl, Tanja van Mourik, Renald Schaub

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)


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 tautomerisation 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.
Original languageEnglish
Pages (from-to)634-639
JournalNano Letters
Issue number2
Early online date28 Jan 2014
Publication statusPublished - 12 Feb 2014


  • STM
  • Tautomerisation
  • Molecular switches
  • Inelastic tunneling


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