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Multi-modal mechanophores based on cinnamate dimers

Author

Listed:
  • Huan Zhang

    (Xiamen University, Xiamen)

  • Xun Li

    (Jilin University, Changchun)

  • Yangju Lin

    (Xiamen University, Xiamen)

  • Fei Gao

    (Xiamen University, Xiamen)

  • Zhen Tang

    (Xiamen University, Xiamen)

  • Peifeng Su

    (Xiamen University, Xiamen)

  • Wenke Zhang

    (Jilin University, Changchun)

  • Yuanze Xu

    (Xiamen University, Xiamen)

  • Wengui Weng

    (Xiamen University, Xiamen)

  • Roman Boulatov

    (University of Liverpool, Donnan Lab)

Abstract

Mechanochemistry offers exciting opportunities for molecular-level engineering of stress-responsive properties of polymers. Reactive sites, sometimes called mechanophores, have been reported to increase the material toughness, to make the material mechanochromic or optically healable. Here we show that macrocyclic cinnamate dimers combine these productive stress-responsive modes. The highly thermally stable dimers dissociate on the sub-second timescale when subject to a stretching force of 1–2 nN (depending on isomer). Stretching a polymer of the dimers above this force more than doubles its contour length and increases the strain energy that the chain absorbs before fragmenting by at least 600 kcal per mole of monomer. The dissociation produces a chromophore and dimers are reformed upon irradiation, thus allowing optical healing of mechanically degraded parts of the material. The mechanochemical kinetics, single-chain extensibility, toughness and potentially optical properties of the dissociation products are tunable by synthetic modifications.

Suggested Citation

  • Huan Zhang & Xun Li & Yangju Lin & Fei Gao & Zhen Tang & Peifeng Su & Wenke Zhang & Yuanze Xu & Wengui Weng & Roman Boulatov, 2017. "Multi-modal mechanophores based on cinnamate dimers," Nature Communications, Nature, vol. 8(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_s41467-017-01412-8
    DOI: 10.1038/s41467-017-01412-8
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    Cited by:

    1. Chenxu Wang & Sergey Akbulatov & Qihan Chen & Yancong Tian & Cai-Li Sun & Marc Couty & Roman Boulatov, 2022. "The molecular mechanism of constructive remodeling of a mechanically-loaded polymer," Nature Communications, Nature, vol. 13(1), pages 1-13, December.
    2. Mengqi Du & Hannes A. Houck & Qiang Yin & Yewei Xu & Ying Huang & Yang Lan & Li Yang & Filip E. Du Prez & Guanjun Chang, 2022. "Force–reversible chemical reaction at ambient temperature for designing toughened dynamic covalent polymer networks," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    3. Tze-Gang Hsu & Shiqi Liu & Xin Guan & Seiyoung Yoon & Junfeng Zhou & Wei-Yuan Chen & Sanjay Gaire & Joshua Seylar & Hanlin Chen & Zeyu Wang & Jared Rivera & Leyao Wu & Christopher J. Ziegler & Ruel Mc, 2023. "Mechanochemically accessing a challenging-to-synthesize depolymerizable polymer," Nature Communications, Nature, vol. 14(1), pages 1-9, December.

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