An Arylazopyrazole-Based N-Heterocyclic Carbene as a Photoswitch on Gold Surfaces: Light-Switchable Wettability, Work Function, and Conductance.
N-heterocyclic carbenes
arylazopyrazoles
electronics
molecular photoswitches
self-assembled monolayers
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
03 Aug 2020
03 Aug 2020
Historique:
received:
08
03
2020
revised:
08
04
2020
pubmed:
10
4
2020
medline:
10
4
2020
entrez:
10
4
2020
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 32271973
doi: 10.1002/anie.202003523
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
13651-13656Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : SFB 858
Organisme : Deutsche Forschungsgemeinschaft
ID : Leibniz Award
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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