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Chlorinated Perylene Monoimide Monoanhydrate Synthesized via Hydrolysis and Its Application in Organic Solar Cells

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Abstract

Perylene-3,4-(dicarboxylic monoimide)-9,10-(dicarboxylic monoanhydrate) (PIA) is one key intermediate to construct functionalized perylene diimides (PDIs) for various applications. However, the difficulty in synthesizing chlorinated PIA hinders the study of chlorinated PDI-based materials. Although chlorination has been widely used to modify the properties of organic semiconductors. We successfully synthesize chlorinated PIA via a simple hydrolysis reaction using LiOH as the base, then a PDI dimer connected at the imide position, N-di-PDI-4Cl, is synthesized as an application example of chlorinated PIA. The heavily chlorinated PDI dimer exhibits deeper energy levels, slightly blue-shifted UV-Vis absorption compared to the non-chlorinated analogue. In addition, the photovoltaic performance of N-di-PDI-4Cl is characterized. This study paves one easy way to synthesize chlorinated PIA and its more delicate derivatives.

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (Nos. 51973169, 51703172 and 52273195), Key R&D program of Hubei Province (No. 2021BAA014), the Natural Science Foundation of Hubei Province (No. 2022CFB097) the Open Project Program of Wuhan National Laboratory for Optoelectronics (No. 2020WNLOKF015), and the science foundation of Wuhan Institute of Technology (No. K202025).

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Hubei Engineering Technology Research Center of Optoelectronic and New Energy Materials, Hubei Key Laboratory of Plasma Chemistry and Advanced Materials, School of Materials Science and Engineering, Wuhan Institute of Technology, Wuhan, 430205, China

    Jian-Hong Gao, Lin-Hua Zhang, Feng-Bo Sun, Xiang Gao, Yan-Jie Sun, Xin-Zhu Tong, Jing Wen, Peng-Cheng Li & Zhi-Tian Liu

  2. School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan, 430070, China

    Hao Shen, Di Wu & Jian-Long Xia

  3. Wuhan National Laboratory for Optoelectronics, Huazhong University of Science and Technology, Wuhan, 430074, China

    Zhi-Tian Liu

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  1. Jian-Hong Gao
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  2. Lin-Hua Zhang
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Correspondence to Xiang Gao, Di Wu or Zhi-Tian Liu.

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Gao, JH., Zhang, LH., Shen, H. et al. Chlorinated Perylene Monoimide Monoanhydrate Synthesized via Hydrolysis and Its Application in Organic Solar Cells. Chin J Polym Sci 41, 1686–1694 (2023). https://doi.org/10.1007/s10118-023-2984-5

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