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Development of twist-bend nematic liquid crystals using sulfur and selenium linkages

Research Project

Project/Area Number 20K15351
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 35030:Organic functional materials-related
Research InstitutionToyohashi University of Technology

Principal Investigator

Arakawa Yuki  豊橋技術科学大学, 工学(系)研究科(研究院), 助教 (30757365)

Project Period (FY) 2020-04-01 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2022: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2021: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2020: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsツイストベンドネマチック相 / 二量体液晶 / 三量体液晶 / 硫黄 / チオエーテル / セレン / セレノエーテル / ツイストベンドネマチック液晶 / 液晶性ダイマー / 液晶性オリゴマー / 第16族元素
Outline of Research at the Start

屈曲した二量体分子がらせん状に凝集して形成される液晶相、ツイストベンドネマチック相(NTB相)はこれまで、二つのメソゲン構造とアルキルスペーサーを炭素や酸素系のリンカーで結んだ分子で報告されている。その課題は、NTB相の温度範囲が狭いことであり、機能性を付与した分子の開発および機能開拓がほとんど行われていない。我々は最近、硫黄およびセレンで結んだ二量体が、従来の分子よりも低温、かつ広い温度範囲でNTB相を形成することを見出した。本研究ではそれらを踏まえ、硫黄およびセレンをリンカーとする機能性分子の開発および機能開拓を行う。

Outline of Final Research Achievements

With the aim of establishing new molecular design for the heliconical twist-bend nematic (NTB) phase, we synthesized, for the first time, sulfur- and selenium-linked bent-shaped liquid crystal (LC) dimers and trimers. The idea is based on smaller bond angles and more flexibility of thioether (C-S-C) and selenoether (C-Se-C) compared with methylene (C-CH2-C) and ether (C-O-C) for more bent shape. A number of thioether- and selenoether-linked dimers and trimers consisting of two mesogenic arms such as cyanobiphenyl, azobenzene, and N-benzylideneaniline were synthesized. It was revealed that thioether and selenoether linkages are very useful in the formation and stabilization of the NTB phase. Remarkably, many LC dimers exhibited the NTB phase that were stable down to room temperature and vitrified. In addition, helical periodic pitches and unique viscoelastic properties of certain dimers were also clarified.

Academic Significance and Societal Importance of the Research Achievements

チオエーテル(C-S-C)およびセレノエーテルは(C-Se-C)は、汎用的なメチレン(C-CH2-C)やエーテル(C-O-C)と比較して小さな結合角および長い結合長により嵩高い置換基となるため、液晶相の形成には不利となることが多い。一方で本研究は、チオエーテルおよびセレノ―エーテルが、ツイストベンドネマチック(NTB)相の形成および安定化にメチレンおよびエーテルよりも優れることを明らかにした。特に、多くの二量体が室温以下までNTB相およびそのガラス状態を保持できる点は従来の二量体を凌駕する特徴の一つである。また、本研究は硫黄およびセレンの有効利用にもつながる点でも社会的な意義がある。

Report

(4 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Research-status Report
  • 2020 Research-status Report
  • Research Products

    (36 results)

All 2023 2022 2021 2020 Other

All Int'l Joint Research (5 results) Journal Article (17 results) (of which Int'l Joint Research: 9 results,  Peer Reviewed: 16 results,  Open Access: 6 results) Presentation (14 results) (of which Invited: 4 results)

  • [Int'l Joint Research] South China University of Technology(中国)

    • Related Report
      2022 Annual Research Report
  • [Int'l Joint Research] University of Silesia in Katowice(ポーランド)

    • Related Report
      2022 Annual Research Report
  • [Int'l Joint Research] South China University of Technology(中国)

    • Related Report
      2021 Research-status Report
  • [Int'l Joint Research] University of Silesia in Katowice(ポーランド)

    • Related Report
      2021 Research-status Report
  • [Int'l Joint Research] Advanced Light Source/Kent State University(米国)

    • Related Report
      2020 Research-status Report
  • [Journal Article] Nontrivial ultraslow dynamics under electric-field in nematics of bent-shaped molecules2023

    • Author(s)
      Aya Satoshi、Tang Wentao、Kong Xian、Arakawa Yuki、Komatsu Kenta、Tsuji Hideto
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 25 Issue: 1 Pages: 297-303

    • DOI

      10.1039/d2cp02407a

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Twist-Bend Nematic Phase Behavior of Cyanobiphenyl-Based Dimers with Propane, Ethoxy, and Ethylthio Spacers2022

    • Author(s)
      Arakawa Yuki、Arai Yuto、Horita Kyohei、Komatsu Kenta、Tsuji Hideto
    • Journal Title

      Crystals

      Volume: 12 Issue: 12 Pages: 1734-1734

    • DOI

      10.3390/cryst12121734

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] 4′-Alkylseleno-4-cyanobiphenyls, SeCB: synthesis and substituent effects on the phase-transition and liquid crystalline behaviors2022

    • Author(s)
      Arakawa Yuki、Shiba Takuma、Igawa Kazunobu、Sasaki Shunsuke、Tsuji Hideto
    • Journal Title

      CrystEngComm

      Volume: 24 Issue: 43 Pages: 7592-7601

    • DOI

      10.1039/d2ce00551d

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Structure of the twist-bend nematic phase with respect to the orientational molecular order of the thioether-linked dimers2022

    • Author(s)
      Kocot Antoni、Loska Barbara、Arakawa Yuki、Merkel Katarzyna
    • Journal Title

      Physical Review E

      Volume: 105 Issue: 4 Pages: 044701-044701

    • DOI

      10.1103/physreve.105.044701

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] 2,7-substituted fluorenone-based liquid crystal trimers: twist-bend nematic phase induced by outer thioether linkage2022

    • Author(s)
      Arakawa Yuki、Komatsu Kenta、Tsuji Hideto
    • Journal Title

      Phase Transitions

      Volume: 95 Issue: 4 Pages: 331-339

    • DOI

      10.1080/01411594.2022.2044040

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Thioether-Linked Liquid Crystal Trimers: Odd-Even Effects of Spacers and the Influence of Thioether Bonds on Phase Behavior2022

    • Author(s)
      Arakawa Yuki、Komatsu Kenta、Ishida Yuko、Shiba Takuma、Tsuji Hideto
    • Journal Title

      Materials

      Volume: 15 Issue: 5 Pages: 1709-1709

    • DOI

      10.3390/ma15051709

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Alkylthio-based asymmetric liquid crystals: unravelling the substituent effects and intercalated cybotactic nematic and smectic phases2022

    • Author(s)
      Arakawa Yuki、Ishida Yuko、Sasaki Yukito、Sasaki Shunsuke、Tokita Masatoshi、Tsuji Hideto
    • Journal Title

      Materials Advances

      Volume: 3 Issue: 7 Pages: 3218-3228

    • DOI

      10.1039/d2ma00050d

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Effects of alkylthio groups on phase transitions of organic molecules and liquid crystals: a comparative study with alkyl and alkoxy groups2022

    • Author(s)
      Arakawa Yuki、Ishida Yuko、Shiba Takuma、Igawa Kazunobu、Sasaki Shunsuke、Tsuji Hideto
    • Journal Title

      CrystEngComm

      Volume: 24 Issue: 10 Pages: 1877-1890

    • DOI

      10.1039/d1ce01470f

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Deuterated Liquid Crystals - practical synthesis of deuterium labeled 4-alkyl-4″-isothiocyanato-[1,1':4',1″]terphenyls2022

    • Author(s)
      Pytlarczyk Marta、Herman Jakub、Arakawa Yuki、Tsuji Hideto、Kula Przemyslaw
    • Journal Title

      Journal of Molecular Liquids

      Volume: 345 Pages: 117847-117847

    • DOI

      10.1016/j.molliq.2021.117847

    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Journal Article] Thioether-linked benzylideneaniline-based twist-bend nematic liquid crystal dimers: Insights into spacer lengths, mesogenic arm structures, and linkage types2021

    • Author(s)
      Arakawa Yuki、Ishida Yuko、Komatsu Kenta、Arai Yuto、Tsuji Hideto
    • Journal Title

      Tetrahedron

      Volume: 95 Pages: 132351-132351

    • DOI

      10.1016/j.tet.2021.132351

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Extreme modulation of liquid crystal viscoelasticity via altering the ester bond direction2021

    • Author(s)
      Tang Wentao、Deng Minghui、Kougo Junichi、Ding Li、Zhao Xiuhu、Arakawa Yuki、Komatsu Kenta、Tsuji Hideto、Aya Satoshi
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 9 Issue: 31 Pages: 9990-9996

    • DOI

      10.1039/d1tc01636a

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Distinct twist-bend nematic phase behaviors associated with the ester-linkage direction of thioether-linked liquid crystal dimers2021

    • Author(s)
      Arakawa Yuki、Komatsu Kenta、Feng Jun、Zhu Chenhui、Tsuji Hideto
    • Journal Title

      Materials Advances

      Volume: 2 Issue: 1 Pages: 261-272

    • DOI

      10.1039/d0ma00746c

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Methylene- and thioether-linked cyanobiphenyl-based liquid crystal dimers CBnSCB exhibiting room temperature twist-bend nematic phases and glasses2021

    • Author(s)
      Arakawa Yuki、Komatsu Kenta、Shiba Takuma、Tsuji Hideto
    • Journal Title

      Materials Advances

      Volume: 2 Issue: 5 Pages: 1760-1773

    • DOI

      10.1039/d0ma00990c

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Carbonyl- and thioether-linked cyanobiphenyl-based liquid crystal dimers exhibiting twist-bend nematic phases2021

    • Author(s)
      Arakawa Yuki、Komatsu Kenta、Ishida Yuko、Igawa Kazunobu、Tsuji Hideto
    • Journal Title

      Tetrahedron

      Volume: 81 Pages: 131870-131870

    • DOI

      10.1016/j.tet.2020.131870

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Phase behaviors of classic liquid crystal dimers and trimers: Alternate induction of smectic and twist-bend nematic phases depending on spacer parity for liquid crystal trimers2021

    • Author(s)
      Arakawa Yuki、Komatsu Kenta、Shiba Takuma、Tsuji Hideto
    • Journal Title

      Journal of Molecular Liquids

      Volume: 326 Pages: 115319-115319

    • DOI

      10.1016/j.molliq.2021.115319

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Manipulation of the nanoscale heliconical structure of a twist-bend nematic material with polarized light2020

    • Author(s)
      Feng C.、Feng J.、Saha R.、Arakawa Y.、Gleeson J.、Sprunt S.、Zhu C.、J?kli A.
    • Journal Title

      Physical Review Research

      Volume: 2 Issue: 3 Pages: 032004-032004

    • DOI

      10.1103/physrevresearch.2.032004

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Thioether-linked azobenzene-based liquid crystal dimers exhibiting the twist-bend nematic phase over a wide temperature range2020

    • Author(s)
      Arakawa Yuki、Komatsu Kenta、Ishida Yuko、Tsuji Hideto
    • Journal Title

      Liquid Crystals

      Volume: 48 Issue: 5 Pages: 641-652

    • DOI

      10.1080/02678292.2020.1800848

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Presentation] チオエーテルおよびエステルで連結したアゾベンゼン系二量体の相転移挙動2022

    • Author(s)
      荒居佑斗、駒津健太、荒川優樹、辻秀人
    • Organizer
      2022年日本液晶学会討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] エステル結合で連結したシアノビフェニル二量体およびフッ素置換体の相転移挙動2022

    • Author(s)
      堀田恭兵、荒川優樹、辻秀人
    • Organizer
      2022年日本液晶学会討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] チオエーテルおよびエステルで連結したアゾベンゼン系ツイストベンドネマチック液晶2021

    • Author(s)
      荒居佑人, 荒川優樹, 辻秀人
    • Organizer
      2021年度東海高分子研究会学生発表会
    • Related Report
      2021 Research-status Report
  • [Presentation] エステル結合で連結したフッ素系シアノビフェニル二量体の相転移挙動2021

    • Author(s)
      堀田恭平, 荒川優樹, 辻秀人
    • Organizer
      2021年度東海高分子研究会学生発表会
    • Related Report
      2021 Research-status Report
  • [Presentation] セレノエーテル結合を有する液晶性オリゴマーとポリマーの合成と相転移挙動2021

    • Author(s)
      芝拓真, 荒川優樹, 辻秀人
    • Organizer
      2021年度東海高分子研究会学生発表会
    • Related Report
      2021 Research-status Report
  • [Presentation] カルコゲンを利用した二量体液晶分子とツイストベンドネマチック相2021

    • Author(s)
      荒川優樹
    • Organizer
      2021年日本液晶学会討論会
    • Related Report
      2021 Research-status Report
    • Invited
  • [Presentation] カルコゲンを利用したツイストベンドネマチック液晶2021

    • Author(s)
      荒川優樹
    • Organizer
      第70回高分子学会年次大会
    • Related Report
      2021 Research-status Report
    • Invited
  • [Presentation] 硫黄およびセレンを利用した屈曲型液晶性 オリゴマーの合成と特性評価2021

    • Author(s)
      荒川優樹
    • Organizer
      東海化学工業会総会 学術賞受賞記念講演
    • Related Report
      2021 Research-status Report
    • Invited
  • [Presentation] チオエーテルで連結したアゾベンゼン系二量体の合成とツイストベンドネ マチック相2020

    • Author(s)
      駒津健太, 荒川優樹, 石田結子, 辻 秀人
    • Organizer
      2020年日本液晶学会オンライン研究発表会
    • Related Report
      2020 Research-status Report
  • [Presentation] カルコゲン元素で連結したシアノビフェニル二量体の合成とツイストベン ドネマチック相2020

    • Author(s)
      芝 拓真, 荒川優樹, 辻 秀人
    • Organizer
      2020年日本液晶学会オンライン研究発表会
    • Related Report
      2020 Research-status Report
  • [Presentation] エーテル結合とチオエーテル結合をリンカー部位に用いたナフタレン系ツイストベンドネマチック液晶2020

    • Author(s)
      荒川優樹、石田結子、辻秀人
    • Organizer
      第69回高分子学会年次大会
    • Related Report
      2020 Research-status Report
  • [Presentation] 硫黄およびセレンを利用したツイストベンドネマチック液晶2020

    • Author(s)
      荒川 優樹
    • Organizer
      2020年 繊維学会秋季研究発表会
    • Related Report
      2020 Research-status Report
    • Invited
  • [Presentation] チオエーテルで連結したアゾベンゼン系ツイストベンドネマチック液晶の合成と相転移挙動2020

    • Author(s)
      駒津健太, 荒川優樹, 石田結子, 辻秀人
    • Organizer
      2020 年度東海高分子研究会学生発表会
    • Related Report
      2020 Research-status Report
  • [Presentation] セレノエーテルをリンカーに導入したシアノビフェニル二量体の合成と相転移挙動2020

    • Author(s)
      芝拓真, 荒川優樹, 辻秀人
    • Organizer
      2020 年度東海高分子研究会学生発表会
    • Related Report
      2020 Research-status Report

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Published: 2020-04-28   Modified: 2024-01-30  

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