Low Bandgap Bistetracene-Based Organic Semiconductors Exhibiting Air Stability, High Aromaticity and Mobility

Kamal Sbargoud, Masashi Mamada, Tanguy Jousselin-Oba, Yasunori Takeda, Shizuo Tokito, Abderrahim Yassar, Jérôme Marrot, Michel Frigoli

Research output: Contribution to journalArticle

9 Citations (Scopus)

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 cm2 V−1 s−1 in 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.

Original languageEnglish
Pages (from-to)5076-5080
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number21
DOIs
Publication statusPublished - Jan 1 2017

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Semiconducting organic compounds
Polycyclic aromatic hydrocarbons
Anthracenes
Energy gap
Organic field effect transistors
Polycyclic Aromatic Hydrocarbons
Air
Electrochemical properties
Optical properties
Anthracene
Derivatives
Oxidation
pentacene
bis(triisopropylsilylethynyl)pentacene
naphthacene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Low Bandgap Bistetracene-Based Organic Semiconductors Exhibiting Air Stability, High Aromaticity and Mobility. / Sbargoud, Kamal; Mamada, Masashi; Jousselin-Oba, Tanguy; Takeda, Yasunori; Tokito, Shizuo; Yassar, Abderrahim; Marrot, Jérôme; Frigoli, Michel.

In: Chemistry - A European Journal, Vol. 23, No. 21, 01.01.2017, p. 5076-5080.

Research output: Contribution to journalArticle

Sbargoud, K, Mamada, M, Jousselin-Oba, T, Takeda, Y, Tokito, S, Yassar, A, Marrot, J & Frigoli, M 2017, 'Low Bandgap Bistetracene-Based Organic Semiconductors Exhibiting Air Stability, High Aromaticity and Mobility', Chemistry - A European Journal, vol. 23, no. 21, pp. 5076-5080. https://doi.org/10.1002/chem.201605906
Sbargoud, Kamal ; Mamada, Masashi ; Jousselin-Oba, Tanguy ; Takeda, Yasunori ; Tokito, Shizuo ; Yassar, Abderrahim ; Marrot, Jérôme ; Frigoli, Michel. / Low Bandgap Bistetracene-Based Organic Semiconductors Exhibiting Air Stability, High Aromaticity and Mobility. In: Chemistry - A European Journal. 2017 ; Vol. 23, No. 21. pp. 5076-5080.
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