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Introduction of Triptycene with a Particular Substitution Pattern into Polymer Chains Can Dramatically Improve the Structural and Rheological Properties

  • Fumitaka Ishiwari*
    Fumitaka Ishiwari
    Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
    *E-mail: [email protected]
  • Gen Okabe
    Gen Okabe
    Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
    More by Gen Okabe
  • Takashi Kajitani
    Takashi Kajitani
    Open Facility Development Office, Open Facility Center, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
  • , and 
  • Takanori Fukushima*
    Takanori Fukushima
    Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
    *E-mail: [email protected]
Cite this: ACS Macro Lett. 2021, 10, 12, 1529–1534
Publication Date (Web):November 16, 2021
https://doi.org/10.1021/acsmacrolett.1c00660
Copyright © 2021 American Chemical Society

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    Abstract

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    Although a large number of polymers that contain triptycene units in the main chains have been developed, no polymer design using 1,8-substituted triptycene has been reported to date. In this study, we investigated the properties of linear homo- and copolymers obtained by ring-opening polymerization of a triptycene monomer bearing a macrocyclic olefin linked at its 1,8-position and its copolymerization with cyclooctene, respectively. We found that the introduction of triptycene with this substitution pattern leads to nanoscale molecular ordering, thereby greatly improving the physical properties of the polymers. The key to this remarkable behavior of 1,8-substituted triptycene-containing polymers is the formation of a particular two-dimensional assembly of the triptycene units by nested hexagonal packing, which aligns one-dimensionally while folding the polymer chains into a well-defined layered structure. The polymer design using 1,8-substituted triptycene can be applied to other polymers, unless their main chain contains functional groups capable of a strong intermolecular interaction such as hydrogen bonding.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsmacrolett.1c00660.

    • The details of literature survey, synthesis, NMR, FT-IR spectra, SEC curves, and dynamic viscoelasticity data (PDF)

    • Literature survey data of triptycene-containing polymers (XLSX)

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    Cited By

    This article is cited by 3 publications.

    1. Jiatong Yu, Ayami Itagaki, Yugen Chen, Tomoya Fukui, Fumitaka Ishiwari, Takashi Kajitani, Takanori Fukushima. Effective Design for Long-Range Polymer Ordering Using Triptycene-Containing Side Chains. Macromolecules 2023, 56 (12) , 4556-4565. https://doi.org/10.1021/acs.macromol.3c00795
    2. Joseph Bedard, Thomas G. Linford-Wood, Benedict C. Thompson, Ulrike Werner-Zwanziger, Katherine M. Marczenko, Rebecca A. Musgrave, Saurabh S. Chitnis. A Robust, Divalent, Phosphaza-bicyclo[2.2.2]octane Connector Provides Access to Cage-Dense Inorganic Polymers and Networks. Journal of the American Chemical Society 2023, 145 (13) , 7569-7579. https://doi.org/10.1021/jacs.3c00882
    3. Yugen Chen, Fumitaka Ishiwari, Tomoya Fukui, Takashi Kajitani, Haonan Liu, Xiaobin Liang, Ken Nakajima, Masatoshi Tokita, Takanori Fukushima. Overcoming the entropy of polymer chains by making a plane with terminal groups: a thermoplastic PDMS with a long-range 1D structural order. Chemical Science 2023, 14 (9) , 2431-2440. https://doi.org/10.1039/D2SC05491D