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A C2-symmetric triple [5]helicene based on N-annulated triperylene hexaimide for chiroptical electronics

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Abstract

Two diastereoisomers (NTPH-P and NTPH-T1) as a C2-symmetric triple [5]helicene based on N-annulated triperylene hexaimide were synthesized. Aided by nuclear magnetic resonance spectroscopy (NMR) and theoretical calculations, NTPH-P was assigned to three-blade propeller conformation while NTPH-T1 tended to exhibit twisted conformation with pyrrole ring fusing on a bowl-shaped PDI foil. Characterized by circular dichroism (CD) and circular polarized luminescence (CPL) measurements, the enantiomerically pure NTPH-P exhibited fairly good chiral activities both in the absorption and emission range with dissymmetry factors ∣gabs∣ of 4.1×10−3 and ∣glum∣ of 1.2×10−3. The diastereoisomers were further employed as acceptors for organic solar cells with distinct PCEs of 8.11% and 5.24% for NTPH-P and NTPH-T1 based devices, respectively, signifying the prospects in chiroptical electronics by designing molecularly defined aromatics.

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Acknowledgements

We thank Dr. Junfeng Xiang at the Institute of Chemistry, Chinese Academy of Sciences for his fruitful suggestions of NMR mearsurements. We thank Dr. Jianlei Han and Prof. Dr. Pengfei Duan for their assistance with CPL spectra measurements and analyses. This work was supported by the National Natural Science Foundation of China (21790361, 21734009), the National Key R&D Program of China (2017YFA0204701), the Youth Innovation Promotion Association of Chinese Academy of Sciences (2017048), and DFG within TRR 61.

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Authors and Affiliations

  1. CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China

    Zetong Ma, Dong Meng, Wei Jiang & Zhaohui Wang

  2. Key Laboratory of Organic Optoelectronics and Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing, 100084, China

    Ningning Liang & Zhaohui Wang

  3. Institute for Solid State Theory and Center for Multiscale Theory & Computation, University of Muenster, Wilhelm-Klemm-Strasse 10, Muenster, 48149, Germany

    Thorsten Winands & Nikos L. Doltsinis

  4. University of Chinese Academy of Sciences, Beijing, 100049, China

    Zetong Ma & Wei Jiang

Authors
  1. Zetong Ma
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  2. Thorsten Winands
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  3. Ningning Liang
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  4. Dong Meng
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  5. Wei Jiang
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  6. Nikos L. Doltsinis
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  7. Zhaohui Wang
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Corresponding authors

Correspondence to Wei Jiang, Nikos L. Doltsinis or Zhaohui Wang.

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Conflict of interest The authors declare that they have no conflict of interest.

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Ma, Z., Winands, T., Liang, N. et al. A C2-symmetric triple [5]helicene based on N-annulated triperylene hexaimide for chiroptical electronics. Sci. China Chem. 63, 208–214 (2020). https://doi.org/10.1007/s11426-019-9632-2

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  • DOI: https://doi.org/10.1007/s11426-019-9632-2

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