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Selenium-containing core-expanded naphthalene diimides for high performance n-type organic semiconductors

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Abstract

The incorporation of heavy atoms into molecular backbone is an extremely straightforward strategy for fine-tuning the optoelectronic properties of organic semiconductors. However, it is rarely studied in n-type small molecules. Herein, by selenium substitution of NDI3HU-DTYM2, two Se-decorated core-expanded naphthalene diimides (NDI) derivatives DTYM-NDI3HU-DSYM (1) and NDI3HU-DSYM2 (2) were synthesized. In comparison with the reference S-containing compound NDI3HU-DTYM2, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of 1 and 2 were fine-tuned with AHOMO of about 0.2 eV, ALUMO of 0.1 eV and the narrowed HOMO-LUMO gaps. More surprisingly, the as-spun organic thin film transistors (OTFTs) based on 1 and 2 both showed μe,sat values as high as 1.0 cm2 V−1 s−1, which are 2-fold higher than that of NDI3HU-DTYM2 with the same device structure and measurement conditions. In addition, the single crystal OFET devices based on Se-containing compound NDI2BO-DSYM2 showed a high value of 1.30 cm V−1 s−1. The molecular packing of NDI2BO-DSYM2 in single crystals (two dimensional supramolecular structure formed by intermolecular Se⋯Se interactions) is quite different from that of a S-containing compound NDI-DTYM2 (one dimensional supramolecular structure formed by intermolecular π-π stacking). Therefore, the Se substitution can cause dramatic change about molecular stacking model, giving rise to high n-type OTFT performance. Our results demonstrated an effective strategy of the heavy atom effect for designing novel organic semiconductors.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21522209, 21790362, 21502218), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB12010100) and the Science and Technology Commission of Shanghai Municipality (19XD1424700, 18JC1410600).

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Centre for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, China

    Wenjie Han, Zhongli Wang, Yunbin Hu, Congwu Ge & Xike Gao

  2. Experiment Center for Science and Technology, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, China

    Xiaodi Yang

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  1. Wenjie Han
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  2. Zhongli Wang
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Correspondence to Congwu Ge or Xike Gao.

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Han, W., Wang, Z., Hu, Y. et al. Selenium-containing core-expanded naphthalene diimides for high performance n-type organic semiconductors. Sci. China Chem. 63, 1182–1190 (2020). https://doi.org/10.1007/s11426-020-9792-3

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