Direct C-H Arylation of Dithiophene-Tetrathiafulvalene: Tuneable Electronic Properties and 2D Self-Assembled Molecular Networks at the Solid/Liquid Interface.

Autor: Ribeiro C; Department of Chemistry, CICECO-Aveiro Institute of Materials, University of Aveiro, Campus de Santiago, Aveiro, 3810-393, Portugal., Valente G; Department of Chemistry, CICECO-Aveiro Institute of Materials, University of Aveiro, Campus de Santiago, Aveiro, 3810-393, Portugal., Espinosa M; Department of Chemistry, CICECO-Aveiro Institute of Materials, University of Aveiro, Campus de Santiago, Aveiro, 3810-393, Portugal., Silva RAL; Centro de Ciências e Tecnologias Nucleares, Instituto Superior Técnico, Universidade de Lisboa, Portugal, E.N. 10, P-2695-066, Bobadela LRS, Portugal., Belo D; Centro de Ciências e Tecnologias Nucleares, Instituto Superior Técnico, Universidade de Lisboa, Portugal, E.N. 10, P-2695-066, Bobadela LRS, Portugal., Gil-Guerrero S; Department of Chemistry, CICECO-Aveiro Institute of Materials, University of Aveiro, Campus de Santiago, Aveiro, 3810-393, Portugal., Arisnabarreta N; Department of Chemistry, Division of Molecular Imaging and Photonics, KU Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium., Mali KS; Department of Chemistry, Division of Molecular Imaging and Photonics, KU Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium., De Feyter S; Department of Chemistry, Division of Molecular Imaging and Photonics, KU Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium., Melle-Franco M; Department of Chemistry, CICECO-Aveiro Institute of Materials, University of Aveiro, Campus de Santiago, Aveiro, 3810-393, Portugal., Souto M; Department of Chemistry, CICECO-Aveiro Institute of Materials, University of Aveiro, Campus de Santiago, Aveiro, 3810-393, Portugal.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2023 Jul 03; Vol. 29 (37), pp. e202300572. Date of Electronic Publication: 2023 May 16.
DOI: 10.1002/chem.202300572
Abstrakt: Tetrathiafulvalene is among the best known building blocks in molecular electronics due to its outstanding electron-donating and redox properties. Among its derivatives, dithiophene-tetrathiafulvalene (DT-TTF) has attracted considerable interest in organic electronics, owing to its high field-effect mobility. Herein, we report the direct C-H arylation of DT-TTF to synthesise mono- and tetraarylated derivatives functionalised with electron-withdrawing and electron-donating groups in order to evaluate their influence on the electronic properties by cyclic voltammetry, UV-vis spectroscopy and theoretical calculations. Self-assembly of the DT-TTF-tetrabenzoic acid derivative was studied by using scanning tunnelling microscopy (STM) which revealed the formation of ordered, densely packed 2D hydrogen-bonded networks at the graphite/liquid interface. The tetrabenzoic acid derivative can attain a planar geometry on the graphite surface due to van der Waals interactions with the surface and H-bonding with neighbouring molecules. This study demonstrates a simple method for the synthesis of arylated DT-TTF derivatives towards the design and construction of novel π-extended electroactive frameworks.
(© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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