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A stable open-shell peri-hexacene with remarkable diradical character

Author

Listed:
  • Jinji Zhang

    (Hunan University of Science and Technology)

  • Xiaojing Fang

    (Hunan University of Science and Technology)

  • Weiwei Niu

    (Nankai University)

  • Yiming Yu

    (Hunan University of Science and Technology)

  • Yanlin Hu

    (Hunan University of Science and Technology)

  • Jiawen Sun

    (Hunan University of Science and Technology)

  • Ying Xu

    (Hunan University of Science and Technology)

  • Zhihua Zhou

    (Hunan University of Science and Technology)

  • Heyuan Liu

    (China University of Petroleum (East China))

  • Xiaonan Fan

    (China University of Petroleum (East China))

  • Baishu Zheng

    (Hunan University of Science and Technology)

  • Qing Jiang

    (Hunan University of Science and Engineering)

  • Guangwu Li

    (Nankai University
    Shenzhen Research Institute of Nankai University)

  • Wangdong Zeng

    (Hunan University of Science and Technology)

Abstract

[n]Peri-acenes ([n]PA) have attracted great interest as promising candidates for nanoelectronics and spintronics. However, the synthesis of large [n]PA (n > 4) is extremely challenging due to their intrinsic open-shell radical character and high reactivity. Herein, we report the successful synthesis and isolation of a derivative (1) of peri-hexacene in crystalline form. The structure of 1 is unequivocally confirmed by X-ray crystallographic analysis. Its ground state, aromaticity and photophysical properties are systematically studied by both experimental methods and theoretical calculations. Although the parent peri-hexacene is calculated to have a very large diradical character (y0 = 94.5%), 1 shows reasonable stability (t1/2 = 24 h under ambient conditions) due to the kinetic blocking. 1 exhibits an open-shell singlet ground state with a small singlet-triplet energy gap (−1.33 kcal/mol from SQUID measurements). 1 has also a narrow HOMO-LUMO energy gap (1.05 eV) and displays amphoteric redox behavior. This work opens new avenues for the design and synthesis of stable zigzag-edged graphene-like molecules with significant diradical character.

Suggested Citation

  • Jinji Zhang & Xiaojing Fang & Weiwei Niu & Yiming Yu & Yanlin Hu & Jiawen Sun & Ying Xu & Zhihua Zhou & Heyuan Liu & Xiaonan Fan & Baishu Zheng & Qing Jiang & Guangwu Li & Wangdong Zeng, 2025. "A stable open-shell peri-hexacene with remarkable diradical character," Nature Communications, Nature, vol. 16(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-024-55556-5
    DOI: 10.1038/s41467-024-55556-5
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