dinaphthotetrathienoacenes; dynamic disorder; organic field-effect transistors; organic semiconductors; thienoacenes; Charge transport properties; Electronic coupling; Innovative design; Physico-chemical characterization; Structure-based; Transfer integral; Medicine (miscellaneous); Chemical Engineering (all); Materials Science (all); Biochemistry, Genetics and Molecular Biology (miscellaneous); Engineering (all); Physics and Astronomy (all); General Physics and Astronomy; General Engineering; General Materials Science; General Chemical Engineering
Abstract :
[en] The charge transport of crystalline organic semiconductors is limited by dynamic disorder that tends to localize charges. It is the main hurdle to overcome in order to significantly increase charge carrier mobility. An innovative design that combines a chemical structure based on sulfur-rich thienoacene with a solid-state herringbone (HB) packing is proposed and the synthesis, physicochemical characterization, and charge transport properties of two new thienoacenes bearing a central tetrathienyl core fused with two external naphthyl rings: naphtho[2,3-b]thieno-[2''',3''':4'',5'']thieno[2″,3″:4',5']thieno[3',2'-b]naphtho[2,3-b]thiophene (DN4T) and naphtho[1,2-b]thieno-[2''',3''':4'',5'']thieno[2'',3'':4',5']thieno[3',2'-b]naphtho[1,2-b]thiophene are presented. Both compounds crystallize with a HB pattern structure and present transfer integrals ranging from 33 to 99 meV (for the former) within the HB plane of charge transport. Molecular dynamics simulations point toward an efficient resilience of the transfer integrals to the intermolecular sliding motion commonly responsible for strong variations of the electronic coupling in the crystal. Best device performances are reached with DN4T with hole mobility up to μ = 2.1 cm2 V-1 s-1 in polycrystalline organic field effect transistors, showing the effectiveness of the electronic coupling enabled by the new aromatic core. These promising results pave the way to the design of high-performing materials based on this new thienoacene, notably through the introduction of alkyl side-chains.
Disciplines :
Chemistry
Author, co-author :
Jouclas, Rémy ; Laboratoire de Chimie des Polymères, Faculté des Sciences, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 206/01, Bruxelles, 1050, Belgium
Liu, Jie; Laboratoire de Chimie des Polymères, Faculté des Sciences, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 206/01, Bruxelles, 1050, Belgium
Volpi, Martina; Laboratoire de Chimie des Polymères, Faculté des Sciences, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 206/01, Bruxelles, 1050, Belgium
Silva de Moraes, Lygia; Laboratoire de Chimie des Polymères, Faculté des Sciences, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 206/01, Bruxelles, 1050, Belgium
Garbay, Guillaume; Laboratoire de Chimie des Polymères, Faculté des Sciences, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 206/01, Bruxelles, 1050, Belgium
Mcintosh, Nemo ; Université de Mons - UMONS > Faculté des Sciences > Service de Chimie des matériaux nouveaux
Bardini, Marco ; Université de Mons - UMONS > Faculté des Sciences > Service de Chimie des matériaux nouveaux
Lemaur, Vincent ; Université de Mons - UMONS > Faculté des Sciences > Service de Chimie des matériaux nouveaux
Gatsios, Christos; Helmholtz-Zentrum Berlin für Materialien und Energie GmbH, 12489, Berlin, Germany ; Institut für Physik and IRIS Adlershof, Humboldt-Universitat zu Berlin, 12489, Berlin, Germany
Modesti, Federico; BASF SE, RCS - J542S, 67056, Ludwigshafen am Rhein, Germany
Turetta, Nicholas; University of Strasbourg, CNRS, ISIS UMR 7006, 8 Alleé Gaspard Monge, Strasbourg, F-67000, France
Beljonne, David ; Université de Mons - UMONS > Faculté des Sciences > Service de Chimie des matériaux nouveaux
Cornil, Jérôme ; Université de Mons - UMONS > Faculté des Sciences > Service de Chimie des matériaux nouveaux
Kennedy, Alan R; Dept. of Pure and Applied Chemistry, University of Strathclyde, Cathedral Street 295, Glasgow, G1 1XL, UK
Koch, Norbert; Helmholtz-Zentrum Berlin für Materialien und Energie GmbH, 12489, Berlin, Germany ; Institut für Physik and IRIS Adlershof, Humboldt-Universitat zu Berlin, 12489, Berlin, Germany
Erk, Peter; BASF SE, RCS - J542S, 67056, Ludwigshafen am Rhein, Germany
Samorì, Paolo; University of Strasbourg, CNRS, ISIS UMR 7006, 8 Alleé Gaspard Monge, Strasbourg, F-67000, France
Schweicher, Guillaume; Laboratoire de Chimie des Polymères, Faculté des Sciences, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 206/01, Bruxelles, 1050, Belgium
Geerts, Yves H ; Laboratoire de Chimie des Polymères, Faculté des Sciences, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 206/01, Bruxelles, 1050, Belgium ; International Solvay Institutes for Physics and Chemistry, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 231, Bruxelles, 1050, Belgium
Institut Universitaire de France LabEx Chimie des Systèmes Complexes Horizon 2020 Framework Programme
Funding text :
This work has received funding from the European Union's Horizon 2020 Research and Innovation Program under the Marie Sklodowska-Curie Grant No 811284. Y.H.G. is thankful to the Belgian National Fund for Scientific Research (FNRS) for financial support through research projects BTBT (No 2.4565.11), Phasetrans (No T.0058.14), Pi-Fast (No T.0072.18), 2D to 3D (No 30489208), and DIFFRA (No U.G001.19). Financial supports from the Fédération Wallonie-Bruxelles (ARC No 20061) are also acknowledged. P.S. acknowledges financial support from the Labex project CSC (ANR-10LABX-0026 CSC) within the Investissement d'Avenir program (ANR-10-IDEX-0002-02), the International Center for Frontier Research in Chemistry, and the Institut Universitaire de France (IUF). G.S. is a FNRS Research Associate. D.B. and J.C. are FNRS Research Directors.This work has received funding from the European Union's Horizon 2020 Research and Innovation Program under the Marie Sklodowska‐Curie Grant No 811284. Y.H.G. is thankful to the Belgian National Fund for Scientific Research (FNRS) for financial support through research projects BTBT (No 2.4565.11), Phasetrans (No T.0058.14), Pi‐Fast (No T.0072.18), 2D to 3D (No 30489208), and DIFFRA (No U.G001.19). Financial supports from the Fédération Wallonie‐Bruxelles (ARC No 20061) are also acknowledged. P.S. acknowledges financial support from the Labex project CSC (ANR‐10LABX‐0026 CSC) within the Investissement d'Avenir program (ANR‐10‐IDEX‐0002‐02), the International Center for Frontier Research in Chemistry, and the Institut Universitaire de France (IUF). G.S. is a FNRS Research Associate. D.B. and J.C. are FNRS Research Directors.
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