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Importance of the Anchor Group Position (Para versus Meta) in Tetraphenylmethane Tripods: Synthesis and Self-Assembly Features

Lindner, Marcin and Valášek, Michal and Homberg, Jan and Edelmann, Kevin and Gerhard, Lukas and Wulfhekel, Wulf and Fuhr, Olaf and Wächter, Tobias and Zharnikov, Michael and Kolivoška, Viliam and Pospíšil, Lubomír and Mészáros, Gábor and Hromadová, Magdaléna and Mayor, Marcel. (2016) Importance of the Anchor Group Position (Para versus Meta) in Tetraphenylmethane Tripods: Synthesis and Self-Assembly Features. Chemistry - A European Journal, 22 (37). pp. 13218-13235.

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Official URL: http://edoc.unibas.ch/52067/

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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 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.
Faculties and Departments:05 Faculty of Science
05 Faculty of Science > Departement Chemie > Chemie > Molecular Devices and Materials (Mayor)
UniBasel Contributors:Mayor, Marcel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley
ISSN:0947-6539
e-ISSN:1521-3765
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:18 Jan 2017 15:17
Deposited On:18 Jan 2017 15:17

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