An Arylazopyrazole-Based N-Heterocyclic Carbene as a Photoswitch on Gold Surfaces: Light-Switchable Wettability, Work Function, and Conductance

D. Thao Nguyen, Matthias Freitag, Christian Gutheil, Kai Sotthewes, Bonnie J. Tyler, Marcus Böckmann, Mowpriya Das, Friederike Schlüter, Nikos L. Doltsinis, Heinrich F. Arlinghaus, Bart Jan Ravoo*, Frank Glorius*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

3 Citations (Scopus)

Abstract

A novel photoresponsive and fully conjugated N-heterocyclic carbene (NHC) has been synthesized that combines the excellent photophysical properties of arylazopyrazoles (AAPs) with an NHC that acts as a robust surface anchor (AAP-BIMe). The formation of self-assembled monolayers (SAMs) on gold was proven by ToF-SIMS and XPS, and the organic film displayed a very high stability at elevated temperatures. This stability was also reflected in a high desorption energy, which was determined by temperature-programmed SIMS measurements. E-/Z-AAP-BIMe@Au photoisomerization resulted in reversible alterations of the surface energy (i.e. wettability), the surface potential (i.e. work function), and the conductance (i.e. resistance). The effects could be explained by the difference in the dipole moment of the isomers. Furthermore, sequential application of a dummy ligand by microcontact printing and subsequent backfilling with AAP-BIMe allowed its patterning on gold. To the best of our knowledge, this is the first example of a photoswitchable NHC on a gold surface. These properties of AAP-BIMe@Au illustrate its suitability as a molecular switch for electronic devices.

Original languageEnglish
Pages (from-to)13651-13656
Number of pages6
JournalAngewandte Chemie - International Edition
Volume59
Issue number32
DOIs
Publication statusPublished - 3 Aug 2020

Keywords

  • UT-Hybrid-D
  • electronics
  • molecular photoswitches
  • N-heterocyclic carbenes
  • self-assembled monolayers
  • arylazopyrazoles

Fingerprint Dive into the research topics of 'An Arylazopyrazole-Based N-Heterocyclic Carbene as a Photoswitch on Gold Surfaces: Light-Switchable Wettability, Work Function, and Conductance'. Together they form a unique fingerprint.

Cite this