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Among its derivatives, dithiophene\u2010tetrathiafulvalene (DT\u2010TTF) has attracted considerable interest in organic electronics, owing to its high field\u2010effect mobility. Herein, we report the direct C\u2212H arylation of DT\u2010TTF to synthesise mono\u2010 and tetraarylated derivatives functionalised with electron\u2010withdrawing and electron\u2010donating groups in order to evaluate their influence on the electronic properties by cyclic voltammetry, UV\u2010vis spectroscopy and theoretical calculations. Self\u2010assembly of the DT\u2010TTF\u2010tetrabenzoic acid derivative was studied by using scanning tunnelling microscopy (STM) which revealed the formation of ordered, densely packed 2D hydrogen\u2010bonded 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\u2010bonding with neighbouring molecules. This study demonstrates a simple method for the synthesis of arylated DT\u2010TTF derivatives towards the design and construction of novel \u03c0\u2010extended electroactive frameworks.<\/jats:p>","DOI":"10.1002\/chem.202300572","type":"journal-article","created":{"date-parts":[[2023,4,6]],"date-time":"2023-04-06T07:16:27Z","timestamp":1680765387000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Direct C\u2212H Arylation of Dithiophene\u2010Tetrathiafulvalene: Tuneable Electronic Properties and 2D Self\u2010Assembled Molecular Networks at the Solid\/Liquid Interface**"],"prefix":"10.1002","volume":"29","author":[{"given":"Catarina","family":"Ribeiro","sequence":"first","affiliation":[{"name":"Department of Chemistry CICECO-Aveiro Institute of Materials University of Aveiro, Campus de Santiago  Aveiro 3810-393 Portugal"}]},{"given":"Gon\u00e7alo","family":"Valente","sequence":"additional","affiliation":[{"name":"Department of Chemistry CICECO-Aveiro Institute of Materials University of Aveiro, Campus de Santiago  Aveiro 3810-393 Portugal"}]},{"given":"Miguel","family":"Espinosa","sequence":"additional","affiliation":[{"name":"Department of Chemistry CICECO-Aveiro Institute of Materials University of Aveiro, Campus de Santiago  Aveiro 3810-393 Portugal"}]},{"given":"Rafaela A. 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