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Thermosalience in Macrocycle-Based Soft Crystals via Anisotropic Deformation of Disilanyl Architecture

  • Kenichiro Omoto
    Kenichiro Omoto
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    Division of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma 630-0192, Japan
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  • , 
  • Toyotaka Nakae
    Toyotaka Nakae
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
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    Orcidhttp://orcid.org/0000-0002-3971-0611
  • , 
  • Masaki Nishio
    Masaki Nishio
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    More by Masaki Nishio
  • , 
  • Yoshinori Yamanoi*
    Yoshinori Yamanoi
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    *[email protected]
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    Orcidhttp://orcid.org/0000-0002-6155-2357
  • , 
  • Hidetaka Kasai
    Hidetaka Kasai
    Division of Physics, Faculty of Pure and Applied Sciences, Tsukuba Research Center for Energy Materials Science (TREMS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan
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  • , 
  • Eiji Nishibori
    Eiji Nishibori
    Division of Physics, Faculty of Pure and Applied Sciences, Tsukuba Research Center for Energy Materials Science (TREMS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan
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    Orcidhttp://orcid.org/0000-0002-4192-6577
  • , 
  • Takaki Mashimo
    Takaki Mashimo
    Division of Applied Chemistry and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
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  • , 
  • Tomohiro Seki
    Tomohiro Seki
    Division of Applied Chemistry and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
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    Orcidhttp://orcid.org/0000-0002-4642-1324
  • , 
  • Hajime Ito
    Hajime Ito
    Division of Applied Chemistry and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
    Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
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    Orcidhttp://orcid.org/0000-0003-3852-6721
  • , 
  • Kazuki Nakamura
    Kazuki Nakamura
    Department of Image and Materials Science, Graduate School of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
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  • , 
  • Norihisa Kobayashi
    Norihisa Kobayashi
    Department of Image and Materials Science, Graduate School of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
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  • , 
  • Naofumi Nakayama
    Naofumi Nakayama
    CONFLEX Corporation, 3-23-17 Takanawa, Minato-ku, Tokyo 108-0074, Japan
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  • , 
  • Hitoshi Goto
    Hitoshi Goto
    Department of Computer Science and Engineering, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580, Japan
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  • , and 
  • Hiroshi Nishihara*
    Hiroshi Nishihara
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    *[email protected]
    More by Hiroshi Nishihara
    Orcidhttp://orcid.org/0000-0002-6568-5640
Cite this: J. Am. Chem. Soc. 2020, 142, 29, 12651–12657
Publication Date (Web):June 22, 2020
https://doi.org/10.1021/jacs.0c03643
Copyright © 2020 American Chemical Society
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    Abstract

    Abstract Image

    We describe here the preparation of soft crystals using disilanyl macrocycle C4 possessing four p-phenylenes circularly connected by four flexible disilane bonds. Single crystals of C4 exhibited a reversible thermal single-crystal-to-single-crystal (SCSC) phase transition behavior between two crystal phases accompanied by remarkable mechanical motion (thermosalient effect), as revealed by thermal analyses and X-ray diffraction measurements. Detailed structural analyses implied that flexibility of the parallelogram disilanyl architecture and molecular packing mode via weak intermolecular interactions facilitated a concerted structural transformation (parallel crank motion) of macrocycles in the crystal, thus resulting in the SCSC phase transition accompanied by anisotropic shrinking/elongation of the cells to induce the thermosalient effect. This work explores a new area of organosilicon chemistry and presents the potential utility of disilanyl macrocycles as soft crystals.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.0c03643.

    • Abbreviations, experimental section, crystal structure of C4, PXRD analysis, visual observation of thermosalient behavior, and theoretical calculations (PDF)

    • Crystallographic data for C4α (CIF)

    • Crystallographic data for C4β (CIF)

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