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In-situ generation of poly(quinolizine)s via catalyst-free polyannulations of activated diyne and pyridines

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Abstract

The development of new polymerization routes to afford N-heterocyclic polymers is of vital importance and highly desired for various practical applications. Herein, a facile and efficient polyannulation reaction of dual-activated alkyne and pyridines was developed to construct novel N-heterocyclic poly(quinolizine)s. This polymerization can proceed smoothly under catalyst-free conditions with 100% atom utilization to furnish poly(quinolizine)s with high molecular weights (up to 34,100) and well-defined structures in acceptable yields. The resulting polymers show good solubility, high thermal stability and strong red emission. Moreover, the prepared poly(quinolizine)s exhibit low cytotoxicity and can selectively label lysosomes in live cells. Considering the remarkable advantages of readily available raw materials, mild polymerization conditions, atom economy, and excellent product performance, this new and efficient polymerization tool will open up enormous opportunities for preparing functional N-heterocyclic polymers.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22101028, 21788102), the start-up funding from Beijing Normal University (310432102, 310432103), the Innovation and Technology Commission (ITC-CNERC14SC01), the Science and Technology Plan of Shenzhen (JCYJ20160229205601482, JCYJ20180507183832744, JCYJ20170818113602462), the Natural Science Foundation of Guangdong Province (2019B121205002), and the Research Grants Council of Hong Kong (16305618, 16304819, 16305320, N-HKUST609/19, C6009-17G, C6014-20W/16).

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Authors and Affiliations

  1. Center for Advanced Materials Research, Science and Technology Experimental Platform, Advanced Institute of Natural Sciences, Beijing Normal University at Zhuhai, Zhuhai, 519085, China

    Benzhao He, Jiachang Huang & Yajun Liu

  2. Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, and Guangdong-Hong Kong-Macao Joint Laboratory of Optoelectronic and Magnetic Functional Materials, The Hong Kong University of Science & Technology, Kowloon, Hong Kong, China

    Benzhao He, Xinyue Liu, Herman H. Y. Sung, Jacky W. Y. Lam & Ben Zhong Tang

  3. Center for AIE Research, College of Materials Science and Engineering, Shenzhen University, Shenzhen, 518060, China

    Jiachang Huang & Dong Wang

  4. Department of Laboratory Medicine, Nanfang Hospital, Southern Medical University, Guangzhou, 510515, China

    Jing Zhang

  5. State Key Laboratory of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates, Center for Aggregation-Induced Emission, South China University of Technology, Guangzhou, 510640, China

    Anjun Qin & Ben Zhong Tang

  6. HKUST-Shenzhen Research Institute, Shenzhen, 518057, China

    Jacky W. Y. Lam & Ben Zhong Tang

  7. Shenzhen Institute of Aggregate Science and Technology, School of Science and Engineering, The Chinese University of Hong Kong, Shenzhen, 518172, China

    Ben Zhong Tang

Authors
  1. Benzhao He
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  2. Jiachang Huang
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  3. Jing Zhang
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  4. Xinyue Liu
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  5. Dong Wang
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  6. Herman H. Y. Sung
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  7. Yajun Liu
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  8. Anjun Qin
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  9. Jacky W. Y. Lam
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  10. Ben Zhong Tang
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Corresponding authors

Correspondence to Jiachang Huang, Jacky W. Y. Lam or Ben Zhong Tang.

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Conflict of interest The authors declare no conflict of interest.

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Supporting information The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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He, B., Huang, J., Zhang, J. et al. In-situ generation of poly(quinolizine)s via catalyst-free polyannulations of activated diyne and pyridines. Sci. China Chem. 65, 789–795 (2022). https://doi.org/10.1007/s11426-021-1225-4

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  • DOI: https://doi.org/10.1007/s11426-021-1225-4

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