IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v16y2025i1d10.1038_s41467-024-55556-5.html
   My bibliography  Save this article

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
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-024-55556-5
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-024-55556-5?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    References listed on IDEAS

    as
    1. Wang, Xue-Sheng & Zhang, Fan & Si, Nan & Meng, Jing & Zhang, Yan-Li & Jiang, Wei, 2019. "Unique magnetic and thermodynamic properties of a zigzag graphene nanoribbon," Physica A: Statistical Mechanics and its Applications, Elsevier, vol. 527(C).
    2. Nikolaos Tombros & Csaba Jozsa & Mihaita Popinciuc & Harry T. Jonkman & Bart J. van Wees, 2007. "Electronic spin transport and spin precession in single graphene layers at room temperature," Nature, Nature, vol. 448(7153), pages 571-574, August.
    3. Young-Woo Son & Marvin L. Cohen & Steven G. Louie, 2006. "Half-metallic graphene nanoribbons," Nature, Nature, vol. 444(7117), pages 347-349, November.
    Full references (including those not matched with items on IDEAS)

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    1. Si, Nan & Su, Xin & Meng, Jing & Miao, Hai-Ling & Zhang, Yan-Li & Jiang, Wei, 2020. "Magnetic properties of decorated 2D kagome-like lattice," Physica A: Statistical Mechanics and its Applications, Elsevier, vol. 560(C).
    2. Osamu Suzuki & Zhidong Zhang, 2021. "A Method of Riemann–Hilbert Problem for Zhang’s Conjecture 1 in a Ferromagnetic 3D Ising Model: Trivialization of Topological Structure," Mathematics, MDPI, vol. 9(7), pages 1-28, April.
    3. Si, Nan & Guan, Yin-Yan & Gao, Wei-Chun & Guo, An-Bang & Zhang, Yan-Li & Jiang, Wei, 2022. "Ferrimagnetism and reentrant behavior in a coronene-like superlattice with double-layer," Physica A: Statistical Mechanics and its Applications, Elsevier, vol. 589(C).
    4. Lidan Guo & Xianrong Gu & Shunhua Hu & Wenchao Sun & Rui Zhang & Yang Qin & Ke Meng & Xiangqian Lu & Yayun Liu & Jiaxing Wang & Peijie Ma & Cheng Zhang & Ankang Guo & Tingting Yang & Xueli Yang & Guor, 2024. "Strain-restricted transfer of ferromagnetic electrodes for constructing reproducibly superior-quality spintronic devices," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    5. Yu Zhou & Xinyu Zhang & Guan Sheng & Shengda Wang & Muqing Chen & Guilin Zhuang & Yihan Zhu & Pingwu Du, 2023. "A metal-free photoactive nitrogen-doped carbon nanosolenoid with broad absorption in visible region for efficient photocatalysis," Nature Communications, Nature, vol. 14(1), pages 1-12, December.
    6. B. G. Márkus & M. Gmitra & B. Dóra & G. Csősz & T. Fehér & P. Szirmai & B. Náfrádi & V. Zólyomi & L. Forró & J. Fabian & F. Simon, 2023. "Ultralong 100 ns spin relaxation time in graphite at room temperature," Nature Communications, Nature, vol. 14(1), pages 1-7, December.
    7. Yu Wang & Xinlei Zhao & Li Yao & Huiru Liu & Peng Cheng & Yiqi Zhang & Baojie Feng & Fengjie Ma & Jin Zhao & Jiatao Sun & Kehui Wu & Lan Chen, 2024. "Orientation-selective spin-polarized edge states in monolayer NiI2," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    8. Dongfei Wang & De-Liang Bao & Qi Zheng & Chang-Tian Wang & Shiyong Wang & Peng Fan & Shantanu Mishra & Lei Tao & Yao Xiao & Li Huang & Xinliang Feng & Klaus Müllen & Yu-Yang Zhang & Roman Fasel & Pasc, 2023. "Twisted bilayer zigzag-graphene nanoribbon junctions with tunable edge states," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    9. Ewelina Szymczykiewicz & Ihor Bordun & Vitalii Maksymych & Myroslava Klapchuk & Zenoviy Kohut & Anatoliy Borysiuk & Yuriy Kulyk & Fedir Ivashchyshyn, 2024. "Charge Storage and Magnetic Properties Nitrogen-Containing Nanoporous Bio-Carbon," Energies, MDPI, vol. 17(4), pages 1-19, February.
    10. Nauman Javed, Rana Muhammad & Al-Othman, Amani & Tawalbeh, Muhammad & Olabi, Abdul Ghani, 2022. "Recent developments in graphene and graphene oxide materials for polymer electrolyte membrane fuel cells applications," Renewable and Sustainable Energy Reviews, Elsevier, vol. 168(C).
    11. Jens Brede & Nestor Merino-Díez & Alejandro Berdonces-Layunta & Sofía Sanz & Amelia Domínguez-Celorrio & Jorge Lobo-Checa & Manuel Vilas-Varela & Diego Peña & Thomas Frederiksen & José I. Pascual & Di, 2023. "Detecting the spin-polarization of edge states in graphene nanoribbons," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
    12. Shengcong Shang & Changsheng Du & Youxing Liu & Minghui Liu & Xinyu Wang & Wenqiang Gao & Ye Zou & Jichen Dong & Yunqi Liu & Jianyi Chen, 2022. "A one-dimensional conductive metal-organic framework with extended π-d conjugated nanoribbon layers," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    13. Wenxuan Zhu & Cheng Song & Lei Han & Tingwen Guo & Hua Bai & Feng Pan, 2022. "Van der Waals lattice-induced colossal magnetoresistance in Cr2Ge2Te6 thin flakes," Nature Communications, Nature, vol. 13(1), pages 1-7, December.
    14. Vladimir S. Prudkovskiy & Yiran Hu & Kaimin Zhang & Yue Hu & Peixuan Ji & Grant Nunn & Jian Zhao & Chenqian Shi & Antonio Tejeda & David Wander & Alessandro Cecco & Clemens B. Winkelmann & Yuxuan Jian, 2022. "An epitaxial graphene platform for zero-energy edge state nanoelectronics," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    15. Guo, An-Bang & Jiang, Wei & Zhang, Na, 2018. "Quantum effects on a graphene-like material with four-sublattice," Physica A: Statistical Mechanics and its Applications, Elsevier, vol. 490(C), pages 1138-1149.
    16. Amelia Carolina Sparavigna, 2023. "The Routes to Magnetic Graphene, from Decorations with Nanoparticles to the Broken Symmetry of its Honeycomb Lattice Bonds," International Journal of Sciences, Office ijSciences, vol. 12(03), pages 51-60, March.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-024-55556-5. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.