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A Series of D–A–D Structured Disilane-Bridged Triads: Structure and Stimuli-Responsive Luminescence Studies
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    A Series of D–A–D Structured Disilane-Bridged Triads: Structure and Stimuli-Responsive Luminescence Studies
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    • Hiroto Miyabe
      Hiroto Miyabe
      Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    • Mizuha Ujita
      Mizuha Ujita
      Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
      More by Mizuha Ujita
    • Masaki Nishio
      Masaki Nishio
      Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    • Toyotaka Nakae
      Toyotaka Nakae
      Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
      Department of Applied Chemistry, Tokyo Metropolitan University, 1-1 Minami-Osawa, Hachioji, Tokyo 192-0397, Japan
    • Tsukasa Usuki
      Tsukasa Usuki
      Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    • Minako Ikeya
      Minako Ikeya
      Department of Chemistry and Life Science, Graduate School of Engineering Science, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, Yokohama, Kanagawa 240-8501, Japan
      More by Minako Ikeya
    • Chika Nishimoto
      Chika Nishimoto
      Department of Chemistry and Life Science, Graduate School of Engineering Science, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, Yokohama, Kanagawa 240-8501, Japan
    • Suguru Ito
      Suguru Ito
      Department of Chemistry and Life Science, Graduate School of Engineering Science, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, Yokohama, Kanagawa 240-8501, Japan
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    • Mineyuki Hattori
      Mineyuki Hattori
      National Institute of Advanced Industrial Science and Technology (AIST), Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan
    • Satoshi Takeya
      Satoshi Takeya
      National Institute of Advanced Industrial Science and Technology (AIST), Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan
    • Shigenobu Hayashi
      Shigenobu Hayashi
      National Institute of Advanced Industrial Science and Technology (AIST), Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan
    • Daisuke Saito
      Daisuke Saito
      Department of Chemistry, Faculty of Science, Hokkaido University, North-10 West-8, Kita-ku, Sapporo 060-0810, Japan
    • Masako Kato
      Masako Kato
      Department of Chemistry, Faculty of Science, Hokkaido University, North-10 West-8, Kita-ku, Sapporo 060-0810, Japan
      Department of Applied Chemistry for Environment, School of Biological and Environmental Sciences, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1330, Japan
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    • Hiroshi Nishihara
      Hiroshi Nishihara
      Research Center for Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan
    • Teppei Yamada
      Teppei Yamada
      Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    • 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: [email protected]
    Other Access OptionsSupporting Information (1)

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2022, 87, 14, 8928–8938
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    https://doi.org/10.1021/acs.joc.2c00641
    Published July 2, 2022
    Copyright © 2022 American Chemical Society

    Abstract

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    A series of σ–π extended octamethyltetrasilanes, which have phenothiazine, 9,9-dimethyl-9,10-dihydroacridine, or phenoxazine (1, 2, and 3) groups as donor moieties and thienopyrazine or benzothiadiazole (a and b) groups as acceptor fragments, has been prepared, and their optical properties have been studied as an extension of our work. All six compounds exhibited fluorescence in the solid state with maximum wavelengths centered in the range of 400 and 650 nm upon excitation by a UV lamp. Compound 2b showed apparent dual emission behavior in solution, which depends on solvent polarity, and a reversible photoluminescent change under mechanical and thermal stimuli in the solid state. Quantum chemical calculations suggest the contribution of a quasi-axial conformer of the 9,9-dimethyl-9,10-dihydroacridine moiety in 2b to the dual emission in solution and the mechanofluoroluminescence in the solid state, similarly to 1a. These studies provide new insight into the preparation of disilane-bridged triads capable of responding to multiple stimuli.

    Copyright © 2022 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.2c00641.

    • Crystallographic data of 2b and 3b, photophysical characteristics in the solid state, absorption and emission spectra in solution, Powder XRD, and Copies of 1H and 13C{1H} NMR for 1b, 2a, 2b, 3a, and 3b (PDF)

    Accession Codes

    CCDC 21581742158175 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Cited By

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    This article is cited by 4 publications.

    1. Yoshinori Yamanoi. Hydrosilane/Organoiodine Coupling-Enabled Studies of Organosilane Physical Properties. Accounts of Chemical Research 2023, 56 (22) , 3325-3341. https://doi.org/10.1021/acs.accounts.3c00599
    2. Preston M. MacQueen, Ryan Holley, Subir Ghorai, Thomas J. Colacot. Convenient One-Pot Synthesis of L2Pd(0) Complexes for Cross-Coupling Catalysis. Organometallics 2023, 42 (18) , 2644-2650. https://doi.org/10.1021/acs.organomet.3c00059
    3. Toyotaka Nakae, Mineyuki Hattori, Yoshinori Yamanoi. 15N CP/MAS NMR as a Tool for the Mechanistic Study of Mechanical Stimuli-Responsive Materials: Evidence for the Conformational Change of an Emissive Dimethylacridane Derivative. ACS Omega 2023, 8 (14) , 12922-12927. https://doi.org/10.1021/acsomega.3c00099
    4. Chuanting Zhou, Zhikuan Zhou, Fuhuan Yu, Wei Xie, Wenjun Zhang, Qiaomei Yang, Xiaodong Xu, Lizhi Gai, Hua Lu. Multi-state photochromism of bis-tetraarylethene luminogens modulated through oligosilane linkages. Journal of Materials Chemistry C 2022, 10 (48) , 18182-18188. https://doi.org/10.1039/D2TC04095F

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2022, 87, 14, 8928–8938
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.2c00641
    Published July 2, 2022
    Copyright © 2022 American Chemical Society

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