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Vinyl-aza-[3]cumulene intermediates induced polymerization for accessing E-dienyl poly(sulfonylamidines) towards pH-responsive drug delivery

Author

Listed:
  • Xuejian Li

    (School of Chemical Engineering, Dalian University of Technology)

  • Qinglong Liu

    (School of Chemical Engineering, Dalian University of Technology)

  • Wangze Song

    (School of Chemical Engineering, Dalian University of Technology
    School of Chemistry, Dalian University of Technology)

  • Nan Zheng

    (School of Chemical Engineering, Dalian University of Technology)

Abstract

The development of reactive intermediates is very significant to construct functional compounds and polymers for multicomponent reactions and multicomponent polymerizations. Heterocumulenes as unique intermediates could be used for the rapid construction of diverse structural skeletons. In this work, a copper-catalyzed multicomponent reaction and polymerization of yne-allylic esters, amines, and azides was disclosed involving so-far unrecognized vinyl alkylidene ketenimine intermediates. Various poly(dienyl-N-sulfonylamidines) were excellently regio- (α-addition) and stereoselectively (E-exclusive) synthesized with molecular weights (7800–26,700 g/mol) and good thermal and chemical stability. Based on the self-assembly of polymers into nanoparticles in water, doxorubicin-loaded nanoparticles (DOX-NPs) were successfully prepared for drug delivery. The drug release results revealed that the DOX-NPs owned sensitive pH-responsive characteristics.

Suggested Citation

  • Xuejian Li & Qinglong Liu & Wangze Song & Nan Zheng, 2025. "Vinyl-aza-[3]cumulene intermediates induced polymerization for accessing E-dienyl poly(sulfonylamidines) towards pH-responsive drug delivery," Nature Communications, Nature, vol. 16(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-65320-y
    DOI: 10.1038/s41467-025-65320-y
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    References listed on IDEAS

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    1. Haiyan Hu & Xuelun Duan & Ming Li & Wangze Song & Haotian Shi & Guofeng Wang & Nan Zheng, 2025. "Selective transformation of propargylic ester towards tunable polymerization pathways," Nature Communications, Nature, vol. 16(1), pages 1-10, December.
    2. Chaochao Yao & Dan-Ran Li & Hua-Ming Xiang & Si-Jia Li & Yuepeng Lu & Zihao Wang & Tingrui Yin & Jiaqiang Wang & Kongling Feng & Cuiju Zhu & Hao Xu, 2024. "Copper-catalysed asymmetric annulation of yne-allylic esters with amines to access axially chiral arylpyrroles," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
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