IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v15y2024i1d10.1038_s41467-024-47252-1.html
   My bibliography  Save this article

Universal inter-molecular radical transfer reactions on metal surfaces

Author

Listed:
  • Junbo Wang

    (Shaanxi Normal University
    Soochow University)

  • Kaifeng Niu

    (Soochow University
    Linköping University)

  • Huaming Zhu

    (Shaanxi Normal University)

  • Chaojie Xu

    (Soochow University)

  • Chuan Deng

    (Shaanxi Normal University)

  • Wenchao Zhao

    (James-Franck-Str. 1)

  • Peipei Huang

    (Shaanxi Normal University)

  • Haiping Lin

    (Shaanxi Normal University)

  • Dengyuan Li

    (East China University of Science & Technology)

  • Johanna Rosen

    (Linköping University)

  • Peinian Liu

    (East China University of Science & Technology)

  • Francesco Allegretti

    (James-Franck-Str. 1)

  • Johannes V. Barth

    (James-Franck-Str. 1)

  • Biao Yang

    (Soochow University
    James-Franck-Str. 1)

  • Jonas Björk

    (Linköping University)

  • Qing Li

    (Shaanxi Normal University)

  • Lifeng Chi

    (Soochow University
    Macau University of Science and Technology)

Abstract

On-surface synthesis provides tools to prepare low-dimensional supramolecular structures. Traditionally, reactive radicals are a class of single-electron species, serving as exceptional electron-withdrawing groups. On metal surfaces, however, such species are affected by conduction band screening effects that may even quench their unpaired electron characteristics. As a result, radicals are expected to be less active, and reactions catalyzed by surface-stabilized radicals are rarely reported. Herein, we describe a class of inter-molecular radical transfer reactions on metal surfaces. With the assistance of aryl halide precursors, the coupling of terminal alkynes is steered from non-dehydrogenated to dehydrogenated products, resulting in alkynyl-Ag-alkynyl bonds. Dehalogenated molecules are fully passivated by detached hydrogen atoms. The reaction mechanism is unraveled by various surface-sensitive technologies and density functional theory calculations. Moreover, we reveal the universality of this mechanism on metal surfaces. Our studies enrich the on-surface synthesis toolbox and develop a pathway for producing low-dimensional organic materials.

Suggested Citation

  • Junbo Wang & Kaifeng Niu & Huaming Zhu & Chaojie Xu & Chuan Deng & Wenchao Zhao & Peipei Huang & Haiping Lin & Dengyuan Li & Johanna Rosen & Peinian Liu & Francesco Allegretti & Johannes V. Barth & Bi, 2024. "Universal inter-molecular radical transfer reactions on metal surfaces," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-47252-1
    DOI: 10.1038/s41467-024-47252-1
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-024-47252-1
    File Function: Abstract
    Download Restriction: no

    File URL: https://libkey.io/10.1038/s41467-024-47252-1?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. Jing Liu & Qiwei Chen & Kang Cai & Jie Li & Yaru Li & Xiao Yang & Yajie Zhang & Yongfeng Wang & Hao Tang & Dahui Zhao & Kai Wu, 2019. "Stepwise on-surface dissymmetric reaction to construct binodal organometallic network," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
    2. Jinming Cai & Pascal Ruffieux & Rached Jaafar & Marco Bieri & Thomas Braun & Stephan Blankenburg & Matthias Muoth & Ari P. Seitsonen & Moussa Saleh & Xinliang Feng & Klaus Müllen & Roman Fasel, 2010. "Atomically precise bottom-up fabrication of graphene nanoribbons," Nature, Nature, vol. 466(7305), pages 470-473, July.
    3. Yi-Qi Zhang & Nenad Kepčija & Martin Kleinschrodt & Katharina Diller & Sybille Fischer & Anthoula C. Papageorgiou & Francesco Allegretti & Jonas Björk & Svetlana Klyatskaya & Florian Klappenberger & M, 2012. "Homo-coupling of terminal alkynes on a noble metal surface," Nature Communications, Nature, vol. 3(1), pages 1-8, January.
    4. Nan Cao & Biao Yang & Alexander Riss & Johanna Rosen & Jonas Björk & Johannes V. Barth, 2023. "On-surface synthesis of enetriynes," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    5. Deng-Yuan Li & Shi-Wen Li & Yu-Li Xie & Xin Hua & Yi-Tao Long & An Wang & Pei-Nian Liu, 2019. "On-surface synthesis of planar dendrimers via divergent cross-coupling reaction," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    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. Lingbo Xing & Jie Li & Yuchen Bai & Yuxuan Lin & Lianghong Xiao & Changlin Li & Dahui Zhao & Yongfeng Wang & Qiwei Chen & Jing Liu & Kai Wu, 2024. "Surface-confined alternating copolymerization with molecular precision by stoichiometric control," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    2. Nan Cao & Biao Yang & Alexander Riss & Johanna Rosen & Jonas Björk & Johannes V. Barth, 2023. "On-surface synthesis of enetriynes," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    3. Austin J. Way & Robert M. Jacobberger & Nathan P. Guisinger & Vivek Saraswat & Xiaoqi Zheng & Anjali Suresh & Jonathan H. Dwyer & Padma Gopalan & Michael S. Arnold, 2022. "Graphene nanoribbons initiated from molecularly derived seeds," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    4. Dasari, Bhagya Lakshmi & Nouri, Jamshid M. & Brabazon, Dermot & Naher, Sumsun, 2017. "Graphene and derivatives – Synthesis techniques, properties and their energy applications," Energy, Elsevier, vol. 140(P1), pages 766-778.
    5. Hiroshi Sakaguchi & Takahiro Kojima & Yingbo Cheng & Shunpei Nobusue & Kazuhiro Fukami, 2024. "Electrochemical on-surface synthesis of a strong electron-donating graphene nanoribbon catalyst," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    6. Dey, Abhijit & Bajpai, Om Prakash & Sikder, Arun K. & Chattopadhyay, Santanu & Shafeeuulla Khan, Md Abdul, 2016. "Recent advances in CNT/graphene based thermoelectric polymer nanocomposite: A proficient move towards waste energy harvesting," Renewable and Sustainable Energy Reviews, Elsevier, vol. 53(C), pages 653-671.
    7. 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.
    8. Zilin Ruan & Baijin Li & Jianchen Lu & Lei Gao & Shijie Sun & Yong Zhang & Jinming Cai, 2023. "Real-space imaging of a phenyl group migration reaction on metal surfaces," Nature Communications, Nature, vol. 14(1), pages 1-6, December.
    9. Olabi, A.G. & Abdelkareem, Mohammad Ali & Wilberforce, Tabbi & Sayed, Enas Taha, 2021. "Application of graphene in energy storage device – A review," Renewable and Sustainable Energy Reviews, Elsevier, vol. 135(C).
    10. Marco Di Giovannantonio & Zijie Qiu & Carlo A. Pignedoli & Sobi Asako & Pascal Ruffieux & Klaus Müllen & Akimitsu Narita & Roman Fasel, 2024. "On-surface cyclization of vinyl groups on poly-para-phenylene involving an unusual pentagon to hexagon transformation," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    11. Outhmane Chahib & Yuling Yin & Jung-Ching Liu & Chao Li & Thilo Glatzel & Feng Ding & Qinghong Yuan & Ernst Meyer & Rémy Pawlak, 2024. "Probing charge redistribution at the interface of self-assembled cyclo-P5 pentamers on Ag(111)," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    12. Anupam Prasoon & Xiaoqing Yu & Mike Hambsch & David Bodesheim & Kejun Liu & Angelica Zacarias & Nguyen Ngan Nguyen & Takakazu Seki & Aerzoo Dianat & Alexander Croy & Gianaurelio Cuniberti & Philippe F, 2023. "Site-selective chemical reactions by on-water surface sequential assembly," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    13. Fouad N. Ajeel & Ali Ben Ahmed, 2023. "Influence of the boron doping and Stone–Wales defects on the thermoelectric performance of graphene nanoribbons," The European Physical Journal B: Condensed Matter and Complex Systems, Springer;EDP Sciences, vol. 96(10), pages 1-10, October.
    14. Ignacio Piquero-Zulaica & Eduardo Corral-Rascón & Xabier Diaz de Cerio & Alexander Riss & Biao Yang & Aran Garcia-Lekue & Mohammad A. Kher-Elden & Zakaria M. Abd El-Fattah & Shunpei Nobusue & Takahiro, 2024. "Deceptive orbital confinement at edges and pores of carbon-based 1D and 2D nanoarchitectures," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    15. Talal Yusaf & Abu Shadate Faisal Mahamude & Kaniz Farhana & Wan Sharuzi Wan Harun & Kumaran Kadirgama & Devarajan Ramasamy & Mohd Kamal Kamarulzaman & Sivarao Subramonian & Steve Hall & Hayder Abed Dh, 2022. "A Comprehensive Review on Graphene Nanoparticles: Preparation, Properties, and Applications," Sustainability, MDPI, vol. 14(19), pages 1-32, September.
    16. Zhenzhe Zhang & Hanh D. M. Pham & Dmytro F. Perepichka & Rustam Z. Khaliullin, 2024. "Prediction of highly stable 2D carbon allotropes based on azulenoid kekulene," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    17. S. E. Ammerman & V. Jelic & Y. Wei & V. N. Breslin & M. Hassan & N. Everett & S. Lee & Q. Sun & C. A. Pignedoli & P. Ruffieux & R. Fasel & T. L. Cocker, 2021. "Lightwave-driven scanning tunnelling spectroscopy of atomically precise graphene nanoribbons," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    18. Yang Luo & Alberto Martin-Jimenez & Michele Pisarra & Fernando Martin & Manish Garg & Klaus Kern, 2023. "Imaging and controlling coherent phonon wave packets in single graphene nanoribbons," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    19. Jinyi Wang & Yihan Zhu & Guilin Zhuang & Yayu Wu & Shengda Wang & Pingsen Huang & Guan Sheng & Muqing Chen & Shangfeng Yang & Thomas Greber & Pingwu Du, 2022. "Synthesis of a magnetic π-extended carbon nanosolenoid with Riemann surfaces," Nature Communications, Nature, vol. 13(1), pages 1-10, December.

    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:15:y:2024:i:1:d:10.1038_s41467-024-47252-1. 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.