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Synthesis and Characterization of Three Pentacene Derivatives

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Abstract

The addition of substituents at the 6,13-position improved the solubility and stability of pentacene, making it possible to use the derivatives in spin coating of organic field-effect transistors (OFETs). Three pentacene derivatives, 6,13-bis(m-tolyl)pentacene (MP), 6,13-bis(4-butylphenyl)pentacene (BP), and 6,13-bis((4-butylphenyl)ethynyl)pentacene (BPEP) were synthesized, and their properties were investigated. 6,13-Pentacenequinone and organolithium were used in the preparation of 6,13-dihydropentacene at 0 °C, and pentacene derivatives were synthesized with SnCl2/HCl as reducing agent, to reduce 6,13-dihydropentacene at room temperature. The structure of the derivatives was characterized using NMR. The thermal stability, photochemical properties, and electronic structure of the three compounds were investigated using TGA, cyclic voltammetry, and UV–Vis. BPEP was also characterized using X-ray diffraction and atom force microscopy. BPEP was used to fabricate an OFET device using spin coating. The device showed a mobility of 0.07 cm2 V s−1 at Vth = − 10 V and ION/IOFF = 102.

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Acknowledgements

This study was supported by the National Natural Science Foundation of China (No. 21102099).

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Authors and Affiliations

  1. Key Laboratory of Systems Bioengineering (Ministry of Education), Tianjin University, Tianjin, 300350, China

    Hongmei Qu, Haijiao Shen, Junqiu Li, Yican Men & Zepeng Chong

  2. Tianjin Kingsrial S&T Co., Ltd, Tianjin, 300384, China

    Xu Chen

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  1. Hongmei Qu
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  2. Haijiao Shen
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  3. Junqiu Li
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  5. Xu Chen
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Correspondence to Hongmei Qu.

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Qu, H., Shen, H., Li, J. et al. Synthesis and Characterization of Three Pentacene Derivatives. Trans. Tianjin Univ. 24, 453–460 (2018). https://doi.org/10.1007/s12209-018-0136-8

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  • DOI: https://doi.org/10.1007/s12209-018-0136-8

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