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Low Bandgap Bistetracene‐Based Organic Semiconductors Exhibiting Air Stability, High Aromaticity and Mobility
Author(s) -
Sbargoud Kamal,
Mamada Masashi,
JousselinOba Tanguy,
Takeda Yasunori,
Tokito Shizuo,
Yassar Abderrahim,
Marrot Jérôme,
Frigoli Michel
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605906
Subject(s) - pentacene , aromaticity , tetracene , ambipolar diffusion , organic semiconductor , band gap , semiconductor , chemical physics , materials science , acene , toluene , chemistry , computational chemistry , optoelectronics , photochemistry , nanotechnology , organic chemistry , molecule , electron , anthracene , thin film transistor , physics , layer (electronics) , quantum mechanics
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 cm 2 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.