Isothianaphthene diimide: an air-stable n-type semiconductor

  • Xiaolong Chen
  • Yaowu He
  • Muhammad Umair Ali
  • Yu He
  • Yanan Zhu
  • Aiyuan Li
  • Changbin Zhao
  • Igor F. Perepichka
  • Hong MengEmail author


Herein, we propose a new strategy to develop air-stable n-type organic semiconductors with non-classical thiophene aromatic diimide derivatives by replacing aromatic naphthalene with a heteroaromatic isothianaphthene core. We designed and successfully synthesized the isothianaphthene core based diimide material, N,N′-bis(n-hexyl)isothianaphthene-2,3,6,7-tetra-carboxylic acid diimide (BTDI-C6) as an n-type semiconductor. Compared to N,N′-bis(n-hexyl)naphthalene-1,4,5,8-tetracarboxylic acid diimide (NDI-C6), BTDI-C6 possesses a deeper LUMO energy level of −4.21 eV, which is 0.32 eV lower than that of NDI-C6. Both molecular modelling and experimental results elucidated that organic thin film transistors (OTFTs) based on both of these materials exhibit comparable mobilities; however, the threshold voltage of BTDI-C6 based device (+7.5 V) is significantly lower than that of NDI-C6 based counterpart (+34 V). Moreover, the low-lying LUMO energy level of BTDI-C6 ensures excellent air-stability which is further validated by the device performance. In addition, BTDI-C6 shows high luminescence while NDI-C6 is not luminescent at all in solution, which reveals the potential application of our newly synthesized material in n-type light-emitting transistors.


isothianaphthene non-classical imide n-type 


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This work was supported by Shenzhen Science and Technology (JCYJ20170412151139619), Shenzhen Engineering Laboratory (Shenzhen development and reform commission [2016]1592), Guangdong Key Research Project (2019B010924003), Guangdong International Science Collaboration Base (2019A050505003), and Shenzhen Peacock Plan (KQTD2014062714543296).

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11426_2019_9555_MOESM1_ESM.doc (4 mb)
Isothianaphthene diimide: an air-stable n-type semiconductor


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Copyright information

© Science China Press and Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Xiaolong Chen
    • 1
  • Yaowu He
    • 1
  • Muhammad Umair Ali
    • 2
  • Yu He
    • 1
  • Yanan Zhu
    • 1
  • Aiyuan Li
    • 1
  • Changbin Zhao
    • 1
  • Igor F. Perepichka
    • 3
  • Hong Meng
    • 1
    Email author
  1. 1.School of Advanced MaterialsPeking University Shenzhen Graduated SchoolShenzhenChina
  2. 2.Department of Materials Science and Engineering, College of EngineeringPeking UniversityBeijingChina
  3. 3.Shaanxi Institute of Flexible ElectronicsNorthwestern Polytechnical UniversityXi’anChina

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