期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 23, 期 21, 页码 5076-5080出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201605906
关键词
acenes; aromaticity; polycyclic aromatic hydrocarbons; semiconductors; thin films
资金
- labex CHARM3AT
- CNRS
- Japan Regional Innovation Strategy Program by the Excellence of Japan Science and Technology Agency (JST)
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- [ANR-16-CE07-0024]
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 1.71eV and an increased stability up to 21times compared to TIPS-PEN and mobility over 0.1cm(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.
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