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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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Main Authors: Lindner, Marcin (Author) , Valášek, Michal (Author) , Homberg, Jan (Author) , Edelmann, Kevin (Author) , Gerhard, Lukas (Author) , Wulfhekel, Wulf (Author) , Fuhr, Olaf (Author) , Wächter, Tobias (Author) , Zharnikov, Michael (Author) , Kolivoška, Viliam (Author) , Pospíšil, Lubomír (Author) , Mészáros, Gábor (Author) , Hromadová, Magdaléna (Author) , Mayor, Marcel (Author)
Format: Article (Journal)
Language:English
Published: 09 August 2016
In: Chemistry - a European journal
Year: 2016, Volume: 22, Issue: 37, Pages: 13218-13235
ISSN:1521-3765
DOI:10.1002/chem.201602019
Online Access: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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Author Notes: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
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Summary: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.
Item Description:Gesehen am 03.06.2020
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201602019

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