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Synthesis of Metalated Pseudorotaxane Polymers with Full Control over the Average Linear Density of Threaded Macrocycles
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    Synthesis of Metalated Pseudorotaxane Polymers with Full Control over the Average Linear Density of Threaded Macrocycles
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    Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409, United States
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2014, 136, 36, 12588–12591
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    https://doi.org/10.1021/ja507167k
    Published August 25, 2014
    Copyright © 2014 American Chemical Society

    Abstract

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    Here we report the synthesis of metalated main-chain polypseudorotaxanes via ring-opening olefin metathesis copolymerization of macrocycles and metalated [2]catenanes. By varying the feed ratio of the macrocycle and the [2]catenate comonomers, we prepared metalated pseudorotaxane polymers with selected, predictable average linear densities of threaded macrocycles that ranged from 0% to 100%, thus allowing, for the first time, both full and fine control over this key parameter.

    Copyright © 2014 American Chemical Society

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    Synthetic procedures, characterization data, NMR spectra, and SEC chromatograms. This material is available free of charge via the Internet at http://pubs.acs.org.

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    This article is cited by 19 publications.

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    2. James E. M. Lewis, Joby Winn, Luca Cera, and Stephen M. Goldup . Iterative Synthesis of Oligo[n]rotaxanes in Excellent Yield. Journal of the American Chemical Society 2016, 138 (50) , 16329-16336. https://doi.org/10.1021/jacs.6b08958
    3. José Augusto Berrocal, Louis M. Pitet, Marko M. L. Nieuwenhuizen, Luigi Mandolini, E. W. Meijer, and Stefano Di Stefano . Ring-Opening Metathesis Polymerization of a Diolefinic [2]-Catenane–Copper(I) Complex: An Easy Route to Polycatenanes. Macromolecules 2015, 48 (5) , 1358-1363. https://doi.org/10.1021/ma502392v
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    9. Thomas P. Nicholls, Chiara Caporale, Massimiliano Massi, Michael G. Gardiner, Alex C. Bissember. Synthesis and characterisation of homoleptic 2,9-diaryl-1,10-phenanthroline copper( i ) complexes: influencing selectivity in photoredox-catalysed atom-transfer radical addition reactions. Dalton Transactions 2019, 48 (21) , 7290-7301. https://doi.org/10.1039/C8DT04116D
    10. Jin-Dong Ding, Jin-Fa Chen, Qi Lin, Hong Yao, You-Ming Zhang, Tai-Bao Wei. A multi-stimuli responsive metallosupramolecular polypseudorotaxane gel constructed by self-assembly of a pillar[5]arene-based pseudo[3]rotaxane via zinc ion coordination and its application for highly sensitive fluorescence recognition of metal ions. Polymer Chemistry 2018, 9 (44) , 5370-5376. https://doi.org/10.1039/C8PY01319E
    11. Deborah Quaglio, Giovanni Zappia, Elisa De Paolis, Silvia Balducci, Bruno Botta, Francesca Ghirga. Olefin metathesis reaction as a locking tool for macrocycle and mechanomolecule construction. Organic Chemistry Frontiers 2018, 5 (20) , 3022-3055. https://doi.org/10.1039/C8QO00728D
    12. Abraham J. P. Teunissen, José Augusto Berrocal, Christiaan H. W. A. Corbet, E. W. Meijer. Supramolecular polymerization of a ureidopyrimidinone‐based [2]catenane prepared via ring‐closing metathesis. Journal of Polymer Science Part A: Polymer Chemistry 2017, 55 (18) , 2971-2976. https://doi.org/10.1002/pola.28694
    13. He‐Lue Sun, Heng‐Yi Zhang, Zhen Dai, Xu Han, Yu Liu. Insights into the Difference Between Rotaxane and Pseudorotaxane. Chemistry – An Asian Journal 2017, 12 (2) , 265-270. https://doi.org/10.1002/asia.201601545
    14. M. Mustafa Cetin, Roman T. Hodson, C. Robin Hart, David B. Cordes, Michael Findlater, Dominick J. Casadonte Jr., Anthony F. Cozzolino, Michael F. Mayer. Characterization and photocatalytic behavior of 2,9-di(aryl)-1,10-phenanthroline copper( i ) complexes. Dalton Transactions 2017, 46 (20) , 6553-6569. https://doi.org/10.1039/C7DT00400A
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    19. José Augusto Berrocal, Simone Albano, Luigi Mandolini, Stefano Di Stefano. A Cu I ‐Based Metallo‐Supramolecular Gel‐Like Material Built from a Library of ­Oligomeric Ligands Featuring Exotopic 1,10‐Phenanthroline Units. European Journal of Organic Chemistry 2015, 2015 (34) , 7504-7510. https://doi.org/10.1002/ejoc.201501201

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2014, 136, 36, 12588–12591
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja507167k
    Published August 25, 2014
    Copyright © 2014 American Chemical Society

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