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Tetraolefin stereospecific photodimerization and photopolymerization in coordination polymers

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Abstract

In the context of the highly desirable design and preparation of smart materials with adjustable properties based on photoreactive compounds, we report two unique photoreactive coordination polymers (CPs),{[Zn(4-Iba)2(4-tkpvb)]·H2O}n(1, 4-HIba = 4-iodobenzoic acid, 4-tkpvb = 1,2,4,5-tetrakis(4-pyridylvinyl)benzene) and [Cd(1,4-bdc)(4-tkpvb)]n (2, 1,4-H2bdc = 1,4-benze-nedicarboxylic acid). Depending on the metal ions and auxiliary carboxylate ligands used, the 4-tkpvb ligands in 1 and 2 adopt different mutual arrangements, which facilitate the photodimerization and photopolymerization reactions in single crystal to single crystal (SCSC) transformations. Upon UV light irradiation which results in the dimerization of the 4-tkpvb ligands, the one-dimensional (1D) zigzag chainsof 1 are transformed into a two-dimensional (2D) network of {[Zn(4-Iba)2(bpbtpvcb)0.5]·H2O}n (1a, bpbtpvcb = 1,3-bis(4-pyridyl)-2,4-bis(2,4,5-tri(2-(4-pyridyl)vinyl) phenylcyclobutane). Similarly, in the crystals of 2, all 4-tkpvb ligands experience a photopolymerization reaction to form an unprecedented 1D linear organic polymer, poly-1,3-bis(4-pyridyl)-2,5-bis(2-(4-pyridyl)-vinyl) phenyl)cyclobutane (poly-bpbpvpcb). Furthermore, the 2D network of 2 is converted into a three-dimensional (3D) framework of [Cdn(1,4-bdc)n(poly-bpbpvpcb)] (2a). This work not only offers a new protocol to selectively synthesize new supramolecular cyclic compounds, but also expands the application of photopolymerization to the synthesis of macromolecules.

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (NSFC No. 21531006, 21871196 and 21773163), the State Key Laboratory of Organometallic Chemistry of Shanghai Institute of Organic Chemistry (No. KF2021005), the Priority Academic Program Development of Jiangsu Higher Education Institutions, the Collaborative Innovation Center of Suzhou Nano Science and Technology, the Project of Scientific and Technologic Infrastructure of Suzhou (No. SZS201905), the Natural Science Research Program of Jiangsu Provincial Department of Education (No. 20KJA150002), Hui-Chun Chin and Tsung-Dao Lee Chinese Undergraduate Research Endowment, and the Huaishang Talent Program of Huaian. We are grateful to the useful comments and suggestions of the editor and the reviewers.

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Authors and Affiliations

  1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, China

    Wei-Jie Gong, Zhan-Yong Yang, Yu-Xuan Hong, Zheng Niu & Jian-Ping Lang

  2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

    Wei-Jie Gong & Jian-Ping Lang

  3. Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian, 223300, China

    Dong Liu

  4. Institut de Chimie (UMR 7177 CNRS), Université de Strasbourg-CNRS, 4 rue Blaise Pascal-CS 90032, Strasbourg, 67081, France

    Pierre Braunstein

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  1. Wei-Jie Gong
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  2. Zhan-Yong Yang
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  4. Dong Liu
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  7. Jian-Ping Lang
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Correspondence to Dong Liu or Jian-Ping Lang.

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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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Gong, WJ., Yang, ZY., Hong, YX. et al. Tetraolefin stereospecific photodimerization and photopolymerization in coordination polymers. Sci. China Chem. 65, 1867–1872 (2022). https://doi.org/10.1007/s11426-022-1313-5

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  • DOI: https://doi.org/10.1007/s11426-022-1313-5

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