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The synthesis, crystal structure and charge-transport properties of hexacene

Nature Chemistry volume 4, pages 574–578 (2012)Cite this article

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Abstract

Acenes can be thought of as one-dimensional strips of graphene and they have the potential to be used in the next generation of electronic devices. However, because acenes larger than pentacene have been found to be unstable, it was generally accepted that they would not be particularly useful materials under normal conditions. Here, we show that, by using a physical vapour-transport method, platelet-shaped crystals of hexacene can be prepared from a monoketone precursor. These crystals are stable in the dark for a long period of time under ambient conditions. In the crystal, the molecules are arranged in herringbone arrays, quite similar to that observed for pentacene. A field-effect transistor made using a single crystal of hexacene displayed a hole mobility significantly higher than that of pentacene. This result suggests that it might be instructive to further explore the potential of other higher acenes.

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Figure 1: Generation of hexacene from precursor 1 by CO expulsion.
Figure 2: Characterization of the transformation from 1 to hexacene.
Figure 3: Absorption spectra of hexacene thin films.
Figure 4: X-ray crystallographic analysis of hexacene.
Figure 5: Single-crystal OFET and conductivity characteristics of hexacene.

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Acknowledgements

The authors thank D.-L.M. Tzou and M.-M. Chen (Academia Sinica) for measuring the CP-MAS 13C NMR spectrum. Computations were carried out using the computer facilities at the Academia Sinica Computing Center. This work was supported by the National Science Council and Academia Sinica in Taiwan.

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Authors and Affiliations

  1. Institute of Chemistry, Academia Sinica, No. 128, Academia Road Sec 2, Nankang, 11529, Taipei, Taiwan

    Motonori Watanabe, Yuan Jay Chang, Md. Minarul Islam, Chih-Hsien Yuan, Yu-Tai Tao & Tahsin J. Chow

  2. Department of Electronic Engineering, Ming Chi University of Technology, No. 84, Gongzhuan Road, Taishan District, New Taipei City, 24301, Taiwan

    Shun-Wei Liu

  3. Department of Chemistry, National Taiwan Normal University, Ting-Chow Road, 11677, Taipei, Taiwan

    Ting-Han Chao

  4. Institute of Materials Chemistry and Engineering (IMCE), Kyushu University, 6-10-1 Hakozaki, Fukuoka, 812-8581, Japan

    Kenta Goto & Teruo Shinmyozu

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  1. Motonori Watanabe
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Contributions

M.W. designed and performed the experiments and theoretical calculations. Y.J.C. measured and analysed the data. S.W.L. and M.M.I. designed the devices and analysed the data. T.H.C. and C.H.Y. fabricated the devices. K.G. carried out X-ray diffraction analysis on the crystals. M.W., Y.T.T. and T.S. co-wrote the paper. T.J.C. supervised the project.

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Correspondence to Tahsin J. Chow.

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Supplementary information

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Crystallographic data for hexacene using Cu radiation. (CIF 28 kb)

Supplementary information

Crystallographic data for hexacene using Mo radiation. (CIF 29 kb)

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Watanabe, M., Chang, Y., Liu, SW. et al. The synthesis, crystal structure and charge-transport properties of hexacene. Nature Chem 4, 574–578 (2012). https://doi.org/10.1038/nchem.1381

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