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Naphthalene diimide based near-infrared luminogens with aggregation-induced emission characteristics for biological imaging and high mobility ambipolar transistors

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Abstract

Organic conjugated materials combining high conductivity with strong solid-state emission are highly desired for organic electronic applications, yet still rather rare. Herein, a novel luminogen (TEN) comprised by linking naphthalene diimides and tri-phenyl ethylene with vinyl bridges is reported. TEN exhibits aggregation-induced emission (AIE) behavior of a strong near-infrared fluorescence over 700 nm and the efficiency above 60.5% in the solid state, while also shows promising application in vivo bio-imaging with good permeability and extremely low background. Single crystal of TEN reveals intra- and intermolecular C-H⋯O hydrogen bonds, contributing to an inclined molecular stacking along the a-axis of the cell, creating a 1D charge carrier transporting channel under a short π-π interaction distance of 3.42 Å, which might benefit the solid emission and charge transport ability simultaneously. Solution processed bottom contact, top gate organic field effect transistors based on TEN reveal a high ambipolar charge transport ability with the hole mobility up to 0.13 cm2 V−1 s−1 and electron mobility up to 0.010 cm2 V−1 s−1. Further atomic force microscopy and X-ray diffraction analysis on TEN thin film confirm the existence of the 1D π-π stacking channel, suggesting the stacking geometry revealed in crystal crucial for facilitating high charge carrier mobility while preserving the strong solid emission at the same time.

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Acknowledgements

This work was supported by the China Scholarship Council, the National Natural Science Foundation of China (21702016, 21905015), the Chongqing Science and Technology Commission (cstc2018jcyjAX0091) and the Fundamental Research Funds for the Central Universities (2019CDQYHG023).

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Chongqing Institute of Green and Intelligent Technology, Chinese Academy of Sciences, Chongqing, 400714, China

    De Guo & Jing Li

  2. University of Chinese Academy of Sciences, Beijing, 100049, China

    De Guo

  3. Beijing Advanced Innovation Center for Soft Matter Science and Engineering, State Key Laboratory of Chemical Resource Engineering, State Key Laboratory of Organic-Inorganic Composite Materials, Beijing Laboratory of Biomedical Materials, Beijing University of Chemical Technology, Beijing, 100029, China

    De Guo, Lin Li, Xianqi Zhu, Qingsong Yu, Zhihua Gan & Xinggui Gu

  4. Department of Chemistry and Centre for Plastic Electronics, Imperial College London, London, W12 0BZ, UK

    Martin Heeney

  5. Chongqing Key Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 401331, China

    Lichun Dong & Luxi Tan

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  1. De Guo
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  2. Lin Li
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  3. Xianqi Zhu
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  10. Luxi Tan
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Correspondence to Xinggui Gu or Luxi Tan.

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11426_2020_9776_MOESM1_ESM.docx

Naphthalene Diimide based Near-infrared Luminogens with Aggregation-Induced Emission Characteristics for Biological Imaging and High Mobility Ambipolar Transistors

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Guo, D., Li, L., Zhu, X. et al. Naphthalene diimide based near-infrared luminogens with aggregation-induced emission characteristics for biological imaging and high mobility ambipolar transistors. Sci. China Chem. 63, 1198–1207 (2020). https://doi.org/10.1007/s11426-020-9776-8

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  • DOI: https://doi.org/10.1007/s11426-020-9776-8

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