Chlorinated Perylene Monoimide Monoanhydrate Synthesized <italic style="font-style: italic">via</italic> Hydrolysis and Its Application in Organic Solar Cells

Jian-Hong Gao; Lin-Hua Zhang; Hao Shen; Feng-Bo Sun; Xiang Gao; Yan-Jie Sun; Xin-Zhu Tong; Jing Wen; Peng-Cheng Li; Di Wu; Jian-Long Xia; Zhi-Tian Liu

doi:10.1007/s10118-023-2984-5

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

RESEARCH ARTICLE | Updated：2023-11-10

- Chlorinated Perylene Monoimide Monoanhydrate Synthesized via Hydrolysis and Its Application in Organic Solar Cells
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- Chlorinated Perylene Monoimide Monoanhydrate Synthesized via Hydrolysis and Its Application in Organic Solar Cells
- 高分子科学（英文版） 2023年41卷第11期页码：1686-1694
- Affiliations：
  
  a.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
  b.School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 430070, China
  c.Wuhan National Laboratory for Optoelectronics, Huazhong University of Science and Technology, Wuhan 430074, China
- Author bio：
  
  xgao@wit.edu.cn (X.G.)
  chemwd@whut.edu.cn (D.W.)
  able.ztliu@wit.edu.cn (Z.T.L.)
- Funds：
  
  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).;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-023-2984-5.
- DOI：10.1007/s10118-023-2984-5
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Gao, J. H.; Zhang, L. H.; Shen, H.; Sun, F. B.; Gao, X.; Sun, Y. J.; Tong, X. Z.; Wen, J.; Li, P. C.; Wu, D.; Xia, J. L.; Liu, Z. T. Chlorinated perylene monoimide monoanhydrate synthesized via hydrolysis and its application in organic solar cells. Chinese J. Polym. Sci. 2023, 41, 1686–1694

Jian-Hong Gao, Lin-Hua Zhang, Hao Shen, et al. Chlorinated Perylene Monoimide Monoanhydrate Synthesized via Hydrolysis and Its Application in Organic Solar Cells[J]. Chinese Journal of Polymer Science, 2023,41(11):1686-1694.
Gao, J. H.; Zhang, L. H.; Shen, H.; Sun, F. B.; Gao, X.; Sun, Y. J.; Tong, X. Z.; Wen, J.; Li, P. C.; Wu, D.; Xia, J. L.; Liu, Z. T. Chlorinated perylene monoimide monoanhydrate synthesized via hydrolysis and its application in organic solar cells. Chinese J. Polym. Sci. 2023, 41, 1686–1694 DOI： 10.1007/s10118-023-2984-5.

Jian-Hong Gao, Lin-Hua Zhang, Hao Shen, et al. Chlorinated Perylene Monoimide Monoanhydrate Synthesized via Hydrolysis and Its Application in Organic Solar Cells[J]. Chinese Journal of Polymer Science, 2023,41(11):1686-1694. DOI： 10.1007/s10118-023-2984-5.

摘要

Chlorinated Perylene-3,4-(dicarboxylic monoimide)-9,10-(dicarboxylic monoanhydrate) (PIA) could be synthesized via a simple hydrolysis reaction using LiOH as the base, then a perylene diimides dimer connected at the imide position, N-di-PDI-4Cl, is synthesized via one-step condensation reaction as an application example of chlorinated PIA.

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.

关键词

Keywords

Chlorinated perylene-34-(dicarboxylic monoimide)-910-(dicarboxylic monoanhydrate)ChlorinationHydrolysisNonfullerene acceptorsOrganic solar cells

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

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

DOI：10.1007/s10118-023-2984-5

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