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Synthesis and Properties of Single Crystals of Organic Molecules with Ordered Orientations

Research Project

Project/Area Number 25288042
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Functional solid state chemistry
Research InstitutionTokyo Metropolitan University

Principal Investigator

Setaka Wataru  首都大学東京, 都市環境科学研究科, 准教授 (60321775)

Co-Investigator(Kenkyū-buntansha) YAMAGUCHI Kentaro  徳島文理大学, 香川薬学部, 教授 (50159208)
Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥18,850,000 (Direct Cost: ¥14,500,000、Indirect Cost: ¥4,350,000)
Fiscal Year 2015: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Fiscal Year 2014: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Fiscal Year 2013: ¥13,650,000 (Direct Cost: ¥10,500,000、Indirect Cost: ¥3,150,000)
Keywords分子機械 / 有機結晶 / 分子運動 / 相転移 / X線結晶構造解析 / 固体NMR / 分子コマ / ヘテロ環化合物 / 機能性分子 / 有機典型元素 / 動的分子 / 構造有機化学 / 双極子配向制御 / 複屈折 / 機能性有機分子 / 光学的性質
Outline of Final Research Achievements

Three-dimensional arrays of dipolar rotors were constructed as single crystals of molecular gyrotops, which are macrocage molecules with a bridged dipolar rotor. In this study, we synthesized novel molecular gyrotops with a five-membered heteroring, i.e., furan-diyl (1), thiophene-diyl (2), and selenophene-diyl (3), and investigated the temperature-dependent orientation and rotation of the dipolar rotors inside the crystal. Unfortunately, furan derivative 1 did not crystallize; however, crystal structures of the other molecular gyrotops, i.e., 2 and 3, showed three-dimensional arrays of dipolar rotors. Thermal order–disorder transitions of the dipolar rotor orientation inside the crystal were observed in 2 and 3. In accordance with the thermal change of the crystal structure, temperature-dependent optical properties of a single crystal were observed by analysis of birefringence of the crystal.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • Research Products

    (48 results)

All 2016 2015 2014 2013 Other

All Journal Article (9 results) (of which Peer Reviewed: 8 results,  Acknowledgement Compliant: 5 results) Presentation (36 results) (of which Int'l Joint Research: 11 results,  Invited: 6 results) Remarks (3 results)

  • [Journal Article] 1,4-Naphthalenediyl-Bridged Molecular Gyrotops: Rotation of the Rotor and Fluorescense in Solution2015

    • Author(s)
      Y. Nishiyama, Y. Inagaki, K. Yamaguchi, W. Setaka
    • Journal Title

      J. Org. Chem.

      Volume: 80 Issue: 20 Pages: 9959-9966

    • DOI

      10.1021/acs.joc.5b01489

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Pyrene-bridged Macrocage Showing No Excimer Fluorescence2015

    • Author(s)
      H. Shionari, Y. Inagaki, K. Yamaguchi, W. Setaka
    • Journal Title

      Org. Biomol. Chem.

      Volume: 13 Issue: 42 Pages: 10511-10516

    • DOI

      10.1039/c5ob01644d

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 結晶性分子ジャイロスコープの構造と回転動力学の密度汎関数強束縛法によるシミュレーション2015

    • Author(s)
      菅野 学, 小林倫仁, Wilfredo Credo Chung, 山崎 馨, 瀬高 渉, 河野裕彦
    • Journal Title

      SENAC

      Volume: 48 Pages: 1-9

    • NAID

      120006576583

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Synthesis of Crystalline Molecular Gyrotops and Phenylene Rotation inside the Cage2014

    • Author(s)
      W. Setaka , K. Inoue, S. Higa, S. Yoshigai, H. Kono, K. Yamaguchi
    • Journal Title

      J. Org. Chem.

      Volume: 79 Issue: 17 Pages: 8288-8295

    • DOI

      10.1021/jo501539h

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Ring-closing metathesis for the synthesis of a molecular gyrotop2014

    • Author(s)
      W. Setaka, S. Higa, K. Yamaguchi
    • Journal Title

      Org. Biomol. Chem.

      Volume: 12 Issue: 21 Pages: 3354-3357

    • DOI

      10.1039/c4ob00470a

    • Related Report
      2014 Annual Research Report 2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A crystalline molecular gyrotop with germanium junctions between a phenylene rotor and alkyl spokes2014

    • Author(s)
      Y. Inagaki, K. Yamaguchi, W. Setaka
    • Journal Title

      RSC Adv.

      Volume: 4 Issue: 102 Pages: 58624-58630

    • DOI

      10.1039/c4ra11705k

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Kinetic stabilization against oxidation reaction induced by a silaalkane cage in thiophene-bridged molecular gyroscope2014

    • Author(s)
      W. Setaka, S. Ohmizu, M. Kira
    • Journal Title

      Chem.Commun.

      Volume: 50 Issue: 9 Pages: 1098-1110

    • DOI

      10.1039/c3cc48205g

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Order-Disorder Transition of Dipolar Rotor in a Crystalline Molecular Gyrotop and Its Optical Change2013

    • Author(s)
      Setaka, W.; Yamaguchi, K.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 135 Issue: 39 Pages: 14560-14563

    • DOI

      10.1021/ja408405f

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cage Size Effects on the Rotation of Molecular Gyrotops with 1,4-Naphthalenediyl Rotor in Solution2013

    • Author(s)
      Setaka, W.; Koyama, A.; Yamaguchi, K.
    • Journal Title

      Org. Lett.

      Volume: 15(19) Issue: 19 Pages: 5092-5095

    • DOI

      10.1021/ol402464d

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] 9,9-ジメチルフルオレンを回転子とする分子ジャイロコマの合成及び蛍光特性2016

    • Author(s)
      吉澤 怜奈・稲垣 佑亮・瀬高 渉
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      同志社大、京田辺
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] フェロセン架橋カゴ型化合物の合成と酸化還元電位2016

    • Author(s)
      高島 英明・稲垣 佑亮・瀬高 渉
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      同志社大、京田辺
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] チオフェン架橋分子ジャイロコマの合成と結晶中の分子運動2016

    • Author(s)
      鶴長 都・稲垣 佑亮・山口 健太郎・瀬高 渉
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      同志社大、京田辺
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] N-メチルカルバゾール架橋分子ジャイロコマの合成と蛍光特性2016

    • Author(s)
      橋本 光・稲垣 佑亮・瀬高 渉
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      同志社大、京田辺
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] A Molecular Gyrotop with Germanium Junctions: Temperature-Dependent Optical Anisotropy of a Crystal2016

    • Author(s)
      Yusuke Inagaki, Kentaro Yamaguchi, Wataru Setaka
    • Organizer
      The 3rd International Symposium for Young Chemists on Stimuli-Responsive Chemical Species for the Creation of Functional Molecules
    • Place of Presentation
      Nagoya University (名古屋)
    • Year and Date
      2016-03-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Phenylene-bridged Macrocages as Crystalline Molecular Gyrotops2016

    • Author(s)
      Wataru SETAKA
    • Organizer
      The 2nd International Forum on Applied Chemistry
    • Place of Presentation
      Tokyo Metropolitan University、Tokyo
    • Year and Date
      2016-03-07
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Crystalline Molecular Gyrotops having a Five-Membered Hetero Aromatic Ring Rotor2015

    • Author(s)
      Wataru SETAKA
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hilton Hawaiian Village (Honolulu, USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Dynamics and optical properties of a selenophene-bridged molecular gyrotops in a crystalline state2015

    • Author(s)
      Toshiyuki MASUDA, Yusuke INAGAKI, Kentaro YAMAGUCHI and Wataru SETAKA
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hawaii Convention Center (Honolulu, USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and birefringence of a molecular gyrotop with a 4,4'-biphenylene rotor2015

    • Author(s)
      Atsushi FUJIWARA, Yusuke INAGAKI, Kentaro YAMAGUCHI and Wataru SETAKA
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hawaii Convention Center (Honolulu, USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Molecular gyrotop with germanium junctions: Dynamics of a phenylene rotor in a crystalline state2015

    • Author(s)
      Yusuke INAGAKI, Kentaro YAMAGUCHI, and Wataru SETAKA
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hawaii Convention Center (Honolulu, USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of 1,4-naphthalenediyl-bridged molecular gyrotops and cage-size effects on dynamics in solution2015

    • Author(s)
      Yohei NISHIYAMA, Akiko KOYAMA, Yusuke INAGAKI, Kentaro YAMAGUCHI and Wataru SETAKA
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hawaii Convention Center (Honolulu, USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of a Novel Molecular Gear having a Germanium Junction and Its Gear Slippage2015

    • Author(s)
      Kazuma OKAMURA, Yusuke INAGAKI, Kentaro YAMAGUCHI and Wataru SETAKA
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hawaii Convention Center (Honolulu, USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and photophysical properties of a pyrene-bridged molecular gyrotop2015

    • Author(s)
      Hirokuni SHIONARI, Yusuke INAGAKI, Kentaro YAMAGUCHI and Wataru SETAKA
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hawaii Convention Center (Honolulu, USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Oriented alignment and dichroism of a p-benzoquinone according to macrocage structure in crystal2015

    • Author(s)
      Kohei SATO, Yusuke INAGAKI, Kentaro YAMAGUCHI and Wataru SETAKA
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hawaii Convention Center (Honolulu, USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] シリル置換セレノフェンの酸化反応における置換基の立体効果2015

    • Author(s)
      増田敏幸・稲垣佑亮・瀬高渉
    • Organizer
      第42回有機典型元素化学討論会
    • Place of Presentation
      名古屋大学(愛知県名古屋市)
    • Year and Date
      2015-12-03
    • Related Report
      2015 Annual Research Report
  • [Presentation] ピレン架橋分子ジャイロコマの合成及び溶液中における立体保護効果2015

    • Author(s)
      塩成博国・稲垣佑亮・山口健太郎・瀬高渉
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学・松山大学(愛媛県松山市)
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] ナフタレン架橋分子ジャイロコマの蛍光消光に対するかご効果2015

    • Author(s)
      西山洋平・小山亜希子・稲垣佑亮・山口健太郎・瀬高渉
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学・松山大学(愛媛県松山市)
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] ビフェニレン架橋分子ジャイロコマの合成と結晶中での動的性質2015

    • Author(s)
      藤原惇志・稲垣佑亮・山口健太郎・瀬高渉
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学・松山大学(愛媛県松山市)
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Order-Disorder Transitions of a Thiophene Rotor in a Crystalline Molecular Gyrotops2015

    • Author(s)
      Wataru Setaka, Toshiyuki Masuda, Junko Arase, Yusuke Inagaki, and Kentaro Yamaguchi
    • Organizer
      16th International Symposium on Novel Aromatic Compounds (ISNA-16)
    • Place of Presentation
      Universidad Complutense (Madrid, Spain)
    • Year and Date
      2015-07-05
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] カゴ化合物による結晶内におけるパラベンゾキノンの配向整列と2色性2015

    • Author(s)
      佐藤 康平・稲垣 佑亮・山口 健太郎・瀬高 渉
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] ビフェニレン架橋分子ジャイロコマの合成と結晶複屈折2015

    • Author(s)
      藤原 惇志・稲垣 佑亮・山口 健太郎・瀬高 渉
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] ピレンを回転子とする分子ジャイロコマの合成と蛍光特性2015

    • Author(s)
      塩成 博国・稲垣 佑亮・山口 健太郎・瀬高 渉
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] セレノフェン架橋分子ジャイロコマの結晶中における回転運動解析と複屈折性2014

    • Author(s)
      増田敏幸・稲垣佑亮・山口健太郎・瀬高 渉
    • Organizer
      第41回有機典型元素化学討論会
    • Place of Presentation
      宇部
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 分子ジャイロコマとしてのπ電子系が架橋したカゴ型化合物2014

    • Author(s)
      瀬高 渉・山口健太郎
    • Organizer
      第15回リング・チューブ超分子研究会シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2014-10-27 – 2014-10-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] ケイ素の特長を利用した分子ジャイロコマの化学2014

    • Author(s)
      瀬高 渉
    • Organizer
      第18回ケイ素化学協会シンポジウム
    • Place of Presentation
      那須塩原
    • Year and Date
      2014-10-17 – 2014-10-18
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] ナフタレン架橋分子ジャイロコマの合成および溶液中における回転子の運動のかごサイズ効果2014

    • Author(s)
      西山 洋平・小山 亜希子・稲垣 佑亮・山口 健太郎・瀬高 渉
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] Chemistry of Molecular Gyrotops2014

    • Author(s)
      Wataru SETAKA
    • Organizer
      Telluride Workshop "Molecular Rotors, Motors, and Switches"
    • Place of Presentation
      Telluride (CO, USA)
    • Year and Date
      2014-06-30 – 2014-07-04
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] かご化合物によるチオフェン環が1軸配向した有機結晶の作成と物性評価2014

    • Author(s)
      瀬高 渉
    • Organizer
      長瀬科学技術振興財団H25年度受賞者研究発表会
    • Place of Presentation
      大阪
    • Year and Date
      2014-04-25
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] ナフタレン架橋分子ジャイロコマの合成と溶液中における回転子の運動2014

    • Author(s)
      西山 洋平・小山 亜希子・稲垣 佑亮・山口 健太郎・瀬高 渉
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(名古屋)
    • Related Report
      2013 Annual Research Report
  • [Presentation] セレノフェン架橋分子ジャイロコマの 合成と性質2014

    • Author(s)
      増田 敏幸・稲垣 佑亮・瀬高 渉
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(名古屋)
    • Related Report
      2013 Annual Research Report
  • [Presentation] シラ炭化水素ロタキサンの温度可変NMRによる軸分子配座解析2014

    • Author(s)
      舛野 大輔・Phan Son Thanh・稲垣 佑亮・吉良 満夫・瀬高 渉
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(名古屋)
    • Related Report
      2013 Annual Research Report
  • [Presentation] ゲルマニウムをかご骨格に導入した分子ジャイロコマの合成と性質2014

    • Author(s)
      稲垣 佑亮・瀬高 渉
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(名古屋)
    • Related Report
      2013 Annual Research Report
  • [Presentation] A Novel Molecular Gyrotop Classified as a Functional Molecular Balloon2013

    • Author(s)
      Wataru Setaka and Kentaro Yamaguchi
    • Organizer
      15th International Symposium on Novel Aromatic Compounds (ISNA-15)
    • Place of Presentation
      Taipei (Taiwan)
    • Related Report
      2013 Annual Research Report
  • [Presentation] チオフェン架橋分子ジャイロコマの結晶構造と複屈折性2013

    • Author(s)
      瀬高 渉・井上 裕美子・高井 杏弥子・山口 健太郎
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学(東京)
    • Related Report
      2013 Annual Research Report
  • [Presentation] ケイ素の特長を利用した分子機械2013

    • Author(s)
      瀬高 渉
    • Organizer
      北里大学理学部第8回セミナー
    • Place of Presentation
      北里大学(相模原)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 結晶中でベンゼン環が回転する分子ジャイロコマの構造有機化学2013

    • Author(s)
      瀬高 渉
    • Organizer
      第388回首都大学東京応化コロキウム
    • Place of Presentation
      首都大学東京(八王子)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Remarks] 首都大学東京 大学院都市環境科学研究科 分子応用化学域 瀬高研究室

    • URL

      http://wwwchem.apchem.ues.tmu.ac.jp/~setaka/

    • Related Report
      2015 Annual Research Report
  • [Remarks] 首都大学東京 大学院都市環境科学研究科分子応用化学域 瀬高研究室

    • URL

      http://wwwchem.apchem.ues.tmu.ac.jp/~setaka/

    • Related Report
      2014 Annual Research Report
  • [Remarks] 首都大学東京 大学院都市環境科学研究科分子応用化学域 瀬高研究室

    • URL

      http://wwwchem.apchem.ues.tmu.ac.jp/~setaka/

    • Related Report
      2013 Annual Research Report

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Published: 2013-05-21   Modified: 2019-07-29  

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