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Aromatic self-assembled monolayers with pentafluoro-λ6-sulfanyl (- SF5) termination: molecular organization and charge transport properties

A series of molecules with oligophenylene backbone, thiolate anchoring group, and pentafluoro-λ6-sulfanyl (−SF5) tail group was synthesized and used as precursors to form self-assembled monolayers (SAMs) on Au(111) substrates. The resulting SAMs feature dense molecular packing, upright molecular ori...

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Main Authors: Liu, Yangbiao (Author) , Zeplichal, Marc (Author) , Katzbach, Sonja (Author) , Wiesner, Adrian (Author) , Das, Saunak (Author) , Terfort, Andreas (Author) , Zharnikov, Michael (Author)
Format: Article (Journal)
Language:English
Published: 2023
In: Nano research
Year: 2023, Volume: 16, Issue: 5, Pages: 7991-8002
ISSN:1998-0000
DOI:10.1007/s12274-022-5350-8
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1007/s12274-022-5350-8
Verlag, kostenfrei, Volltext: https://link.springer.com/article/10.1007/s12274-022-5350-8
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Author Notes:Yangbiao Liu, Marc Zeplichal, Sonja Katzbach, Adrian Wiesner, Saunak Das, Andreas Terfort, and Michael Zharnikov

MARC

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520 |a A series of molecules with oligophenylene backbone, thiolate anchoring group, and pentafluoro-λ6-sulfanyl (−SF5) tail group was synthesized and used as precursors to form self-assembled monolayers (SAMs) on Au(111) substrates. The resulting SAMs feature dense molecular packing, upright molecular orientation, and chemically homogeneous SAM-ambient interface, comprised entirely of the −SF5 moieties. These SAMs exhibit exceptional wetting and electrostatic properties, showing advancing water contact angles up to 103° and work function values up to 5.96 eV—probably the highest values reported for any aromatic monolayers on gold. They also feature a comparably low value of the tunnelling decay coefficient (0.38 ± 0.07 Å−1), typical of oligophenylene backbone, which is not affected by the introduction of the −SF5 group. The latter also hardly affects the current densities at a specific bias compared to analogous monolayers with other electronegative tail groups. The superior electrostatic and good charge transport properties of the designed, SF5-terminated SAMs make them potentially useful for interface engineering in organic electronics and photovoltaics. 
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