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Palladium-Catalyzed Cross-Coupling Polymerization: A New Access to Cross-Conjugated Polymers with Modifiable Structure and Tunable Optical/Conductive Properties

  • Kunming Jiang
    Kunming Jiang
    State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200433, China
  • Lu Zhang
    Lu Zhang
    State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200433, China
    Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China
    More by Lu Zhang
  • Yucheng Zhao
    Yucheng Zhao
    State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200433, China
    More by Yucheng Zhao
  • Jun Lin
    Jun Lin
    Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China
    More by Jun Lin
  • , and 
  • Mao Chen*
    Mao Chen
    State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200433, China
    *(M.C.) E-mail: [email protected]
    More by Mao Chen
Cite this: Macromolecules 2018, 51, 23, 9662–9668
Publication Date (Web):November 21, 2018
https://doi.org/10.1021/acs.macromol.8b02163
Copyright © 2018 American Chemical Society

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    Abstract

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    While the synthesis of conjugated polymers has received significant attention, the preparation of cross-conjugated polymers, where the π-electron delocalization cannot extend along the backbone, has received much less success. We have exploited a new catalytic polymerization process and developed the Pd-catalyzed cross-coupling enabled synthesis of cross-conjugated polymers with readily accessible N-tosylhydrazones and aryl halides. A broad scope of cross-conjugated polymers with good processability and thermal stability has been prepared in high yields using dialkylbiarylphospine–Pd precatalysts. Owing to their unique vinyl structures, these polymers could be easily modified in postpolymerization fashions to impart high degrees of structural complexities. Moreover, these materials were shown to have interesting and tunable optical and conductive properties, featuring their great potentials in a variety of applications.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.macromol.8b02163.

    • Condition optimizations; 1H NMR, 13C NMR, DSC, TGA, and IR analyses of polymers; optical properties of polymer solutions; 1H NMR and 13C NMR analyses of monomers (PDF)

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    Cited By

    This article is cited by 21 publications.

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    2. Benfa Chu, Xuan Wu, Ziwen Fu, Weiping Wu, Bin Wang, Jin Zhu. Rhodium-Catalyzed Redox-Neutral Cross-Dehydrogenative Alkenylation of Arylhydrazines for Polymer Synthesis. Macromolecules 2021, 54 (20) , 9739-9749. https://doi.org/10.1021/acs.macromol.1c01664
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    12. Qinqin Shi, Xiaosong Shi, Changfu Feng, Yishi Wu, Nan Zheng, Jie Liu, Xiaoxi Wu, Hao Chen, Aidong Peng, Jianfeng Li, Lang Jiang, Hongbing Fu, Zengqi Xie, Seth R. Marder, Simon B. Blakey, Hui Huang. Synthetic Routes for Heteroatom‐Containing Alkylated/Arylated Polycyclic Aromatic Hydrocarbons. Angewandte Chemie 2021, 133 (6) , 2960-2964. https://doi.org/10.1002/ange.202014108
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    14. Xin Gao, Qirui Zhang, Jianfeng Hu, Hao Zhang. Ferrocene-containing cross-conjugated polymers synthesized by palladium-catalyzed cross-coupling polymerization. Polymer 2020, 207 , 122827. https://doi.org/10.1016/j.polymer.2020.122827
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    18. Nengbo Zhu, Mong-Feng Chiou, Haigen Xiong, Min Su, Muqiao Su, Yajun Li, Wen-Ming Wan, Hongli Bao. The Introduction of the Radical Cascade Reaction into Polymer Chemistry: A One-Step Strategy for Synchronized Polymerization and Modification. iScience 2020, 23 (3) , 100902. https://doi.org/10.1016/j.isci.2020.100902
    19. Xin Gao, Lei Deng, Jianfeng Hu, Hao Zhang. Ferrocene-Containing Conjugated Oligomers Synthesized by Acyclic Diene Metathesis Polymerization. Polymers 2019, 11 (8) , 1334. https://doi.org/10.3390/polym11081334
    20. Toshio Koizumi, Tsuyoshi Kameda, Hironori Saito, Ayumu Sato, Shotaro Hayashi. Facile synthesis of ortho ‐Phenylene‐based conjugated polymers through transformation of cross‐conjugated poly(2,3‐diaryl[2]dendralene)s and their optical properties. Journal of Polymer Science Part A: Polymer Chemistry 2019, 57 (7) , 827-832. https://doi.org/10.1002/pola.29333
    21. Qi Zhou, Yunpeng Gao, Yiyang Xiao, Lefei Yu, Zihao Fu, Zichen Li, Jianbo Wang. Palladium-catalyzed carbene coupling of N -tosylhydrazones and arylbromides to synthesize cross-conjugated polymers. Polymer Chemistry 2019, 10 (5) , 569-573. https://doi.org/10.1039/C8PY01529E

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