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Importance of the Anchor Group Position ( Para versus Meta ) in Tetraphenylmethane Tripods: Synthesis and Self‐Assembly Features
Author(s) -
Lindner Marcin,
Valášek Michal,
Homberg Jan,
Edelmann Kevin,
Gerhard Lukas,
Wulfhekel Wulf,
Fuhr Olaf,
Wächter Tobias,
Zharnikov Michael,
Kolivoška Viliam,
Pospíšil Lubomír,
Mészáros Gábor,
Hromadová Magdaléna,
Mayor Marcel
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602019
Subject(s) - group (periodic table) , position (finance) , physics , business , finance , quantum mechanics
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 sp 3 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.