Dinaphthotetrathienoacenes: Synthesis, Characterization, and Applications in Organic Field-Effect Transistors.

Autor: Jouclas R; Laboratoire de Chimie des Polymères, Faculté des Sciences, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 206/01, Bruxelles, 1050, Belgium., Liu J; Laboratoire de Chimie des Polymères, Faculté des Sciences, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 206/01, Bruxelles, 1050, Belgium., Volpi M; 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 L; Laboratoire de Chimie des Polymères, Faculté des Sciences, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 206/01, Bruxelles, 1050, Belgium., Garbay G; Laboratoire de Chimie des Polymères, Faculté des Sciences, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 206/01, Bruxelles, 1050, Belgium., McIntosh N; Laboratory for Chemistry of Novel Materials, Center for Research in Molecular Electronics and Photonics, University of Mons, Place du Parc 23, Mons, B-7000, Belgium., Bardini M; Laboratory for Chemistry of Novel Materials, Center for Research in Molecular Electronics and Photonics, University of Mons, Place du Parc 23, Mons, B-7000, Belgium., Lemaur V; Laboratory for Chemistry of Novel Materials, Center for Research in Molecular Electronics and Photonics, University of Mons, Place du Parc 23, Mons, B-7000, Belgium., Vercouter A; Laboratory for Chemistry of Novel Materials, Center for Research in Molecular Electronics and Photonics, University of Mons, Place du Parc 23, Mons, B-7000, Belgium., Gatsios C; 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 F; BASF SE, RCS - J542S, 67056, Ludwigshafen am Rhein, Germany., Turetta N; University of Strasbourg, CNRS, ISIS UMR 7006, 8 Alleé Gaspard Monge, Strasbourg, F-67000, France., Beljonne D; Laboratory for Chemistry of Novel Materials, Center for Research in Molecular Electronics and Photonics, University of Mons, Place du Parc 23, Mons, B-7000, Belgium., Cornil J; Laboratory for Chemistry of Novel Materials, Center for Research in Molecular Electronics and Photonics, University of Mons, Place du Parc 23, Mons, B-7000, Belgium., Kennedy AR; Dept. of Pure and Applied Chemistry, University of Strathclyde, Cathedral Street 295, Glasgow, G1 1XL, UK., Koch N; 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 P; BASF SE, RCS - J542S, 67056, Ludwigshafen am Rhein, Germany., Samorì P; University of Strasbourg, CNRS, ISIS UMR 7006, 8 Alleé Gaspard Monge, Strasbourg, F-67000, France., Schweicher G; Laboratoire de Chimie des Polymères, Faculté des Sciences, Université Libre de Bruxelles (ULB), Boulevard du Triomphe, CP 206/01, Bruxelles, 1050, Belgium., Geerts YH; 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.
Jazyk: angličtina
Zdroj: Advanced science (Weinheim, Baden-Wurttemberg, Germany) [Adv Sci (Weinh)] 2022 Jul; Vol. 9 (19), pp. e2105674. Date of Electronic Publication: 2022 Mar 16.
DOI: 10.1002/advs.202105674
Abstrakt: 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 cm 2 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.
(© 2022 The Authors. Advanced Science published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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