title: Low Bandgap Bistetracene-Based Organic Semiconductors Exhibiting Air Stability, High Aromaticity and Mobility.
abstract: The benchmark of soluble organic semiconductors based on acenes is the 6,13-bis(triisopropylsilylethynyl)pentacene (TIPS-PEN). However TIPS-PEN still suffers from photoinduced oxidation due to its low degree of aromaticity. Increasing the aromaticity while keeping similar optical and electrochemical properties as well as a shape suitable for good hole transport can be achieved with two-dimensional polycyclic aromatic hydrocarbons (2D-PAHs). Herein, we present an efficient synthesis and characterization of bistetracene derivatives that exhibit a band gap up to 1.71 eV and an increased stability up to 21 times compared to TIPS-PEN and mobility over 0.1 cm2V-1s-1in solution-processed organic field-effect transistors. Based on simple structural consideration, the high stability is attributed to the aromaticity of the bistetracene which is comparable to an anthrancene along each tetracene. According to Clar's sextet rule, the bistetracene should be best regarded as two anthracenes fused at the face bridged by two ethylenic spacers. The synthesis path paves the way towards the preparation of ambipolar and/or longer 2D-PAHs such as bispentacenes and could give rise to organic semiconductors with interesting properties.
authors.affiliation: UMR CNRS 8180, Institut Lavoisier de Versailles, UVSQ, Université Paris-Saclay, France.
authors.forename: Kamal
authors.initials: K
authors.lastname: Sbargoud
authors.affiliation: Center for Organic Photonics and Electronics Research, Kyushu University, Japan.
authors.forename: Masashi
authors.initials: M
authors.lastname: Mamada
authors.affiliation: UMR CNRS 8180, Institut Lavoisier de Versailles, UVSQ, Université Paris-Saclay, France.
authors.forename: Tanguy
authors.initials: T
authors.lastname: Jousselin-Oba
authors.affiliation: Graduate School of Science and Engineering, Yamagata University, Japan.
authors.forename: Yasunori
authors.initials: Y
authors.lastname: Takeda
authors.affiliation: Graduate School of Science and Engineering, Yamagata University, Japan.
authors.forename: Shizuo
authors.initials: S
authors.lastname: Tokito
authors.affiliation: UMR CNRS 7647, LPICM-École Polytechnique, Université Paris-Saclay, France.
authors.forename: Abderrahim
authors.initials: A
authors.lastname: Yassar
authors.affiliation: UMR CNRS 8180, Institut Lavoisier de Versailles, UVSQ, Université Paris-Saclay, France.
authors.forename: Jérôme
authors.initials: J
authors.lastname: Marrot
authors.affiliation: UMR CNRS 8180, Institut Lavoisier de Versailles, UVSQ, Université Paris-Saclay, France.
authors.forename: Michel
authors.identifier: http://orcid.org/0000-0001-5576-1868
authors.initials: M
authors.lastname: Frigoli
keywords: acenes; aromaticity; polycyclic aromatic hydrocarbons; semiconductors; thin films