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CH2, NH, and O heteroatom substitution effects on the electronic, optical, and charge transport properties of a 2,1,3-benzothiadiazole-based derivative: Insights from theory

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Abstract

A set of CH2-, NH-, and O-substituted 2,1,3-benzothiadiazole (BTD)-based derivatives have been investigated theoretically in order to explore their electronic, optical, and charge transport properties. The calculation results show that the electronic and optical properties of the pristine molecule can be easily tuned through changing the S substituent in the central aromatic ring. Based on the calculated maximum emission wavelength, we predict that CH2-, NH-, and O-substituted BTD-based derivatives could be used as red, green, and orange light-emitting materials, respectively. After CH2-, NH- or O-substitution, the oscillator strengths of the emission spectra are enhanced with respect to that of the pristine molecule, implying that these compounds have larger fluorescence intensity. Finally, it can be deduced that CH2-, NH-, and O-substituted BTD-based derivatives may act as hole transport materials in organic light-emitting diodes.

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Authors and Affiliations

  1. Faculty of Chemistry, Jilin Normal University, Siping, 136000, China

    Bo Hu, Chan Yao & QingWei Wang

  2. Key Laboratory of Preparation and Applications of Environmental Friendly Materials (Jilin Normal University), Ministry of Education, Siping, 136000, China

    Bo Hu, Chan Yao & QingWei Wang

  3. State Key Laboratory of Theoretical and Computational Chemistry, Jilin University, Changchun, 130023, China

    Hao Zhang & JianKang Yu

  4. Institute of Applied Physics and Technology, Foundation Department of Liaoning Technical University, Huludao, 123000, China

    JianKang Yu

Authors
  1. Bo Hu
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  2. Chan Yao
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  3. QingWei Wang
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  4. Hao Zhang
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Correspondence to Bo Hu.

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Hu, B., Yao, C., Wang, Q. et al. CH2, NH, and O heteroatom substitution effects on the electronic, optical, and charge transport properties of a 2,1,3-benzothiadiazole-based derivative: Insights from theory. Sci. China Chem. 55, 1364–1369 (2012). https://doi.org/10.1007/s11426-012-4583-0

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