Importance of the anchor group position (para versus meta) in tetraphenylmethane tripods: synthesis and self-assembly features

Abstract The efficient synthesis of tripodal platforms based on tetraphenylmethane with three acetyl-protected thiol groups in either meta or para positions relative to the central sp3 carbon for deposition on Au (111) surfaces is reported. These platforms are intended to provide a vertical arrangem...

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Hauptverfasser: Lindner, Marcin (VerfasserIn) , Valášek, Michal (VerfasserIn) , Homberg, Jan (VerfasserIn) , Edelmann, Kevin (VerfasserIn) , Gerhard, Lukas (VerfasserIn) , Wulfhekel, Wulf (VerfasserIn) , Fuhr, Olaf (VerfasserIn) , Wächter, Tobias (VerfasserIn) , Zharnikov, Michael (VerfasserIn) , Kolivoška, Viliam (VerfasserIn) , Pospíšil, Lubomír (VerfasserIn) , Mészáros, Gábor (VerfasserIn) , Hromadová, Magdaléna (VerfasserIn) , Mayor, Marcel (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 09 August 2016
In: Chemistry - a European journal
Year: 2016, Jahrgang: 22, Heft: 37, Pages: 13218-13235
ISSN:1521-3765
DOI:10.1002/chem.201602019
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201602019
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201602019
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Verfasserangaben:Marcin Lindner, Michal Valášek, Jan Homberg, Kevin Edelmann, Lukas Gerhard, Wulf Wulfhekel, Olaf Fuhr, Tobias Wächter, Michael Zharnikov, Viliam Kolivoška, Lubomír Pospíšil, Gábor Mészáros, Magdaléna Hromadová, and Marcel Mayor

MARC

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520 |a Abstract The efficient synthesis of tripodal platforms based on tetraphenylmethane with three acetyl-protected thiol groups in either meta or para positions relative to the central sp3 carbon for deposition on Au (111) surfaces is reported. These platforms are intended to provide a vertical arrangement of the substituent in position?4 of the perpendicular phenyl ring and an electronic coupling to the gold substrate. The self-assembly features of both derivatives are analyzed on Au (111) surfaces by low-temperature ultra-high-vacuum STM, high-resolution X-ray photoelectron spectroscopy, near-edge X-ray absorption fine structure spectroscopy, and reductive voltammetric desorption studies. These experiments indicated that the meta derivative forms a well-ordered monolayer, with most of the anchoring groups bound to the surface, whereas the para derivative forms a multilayer film with physically adsorbed adlayers on the chemisorbed para monolayer. Single-molecule conductance values for both tripodal platforms are obtained through an STM break junction experiment. 
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