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Constructions and Applications of Cavitand-Based Capsules as Functional Self-Assembled Nanospace

Research Project

Project/Area Number 25288034
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

KOBAYASHI Kenji  静岡大学, 理学部, 教授 (40225503)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥18,720,000 (Direct Cost: ¥14,400,000、Indirect Cost: ¥4,320,000)
Fiscal Year 2015: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2014: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2013: ¥11,700,000 (Direct Cost: ¥9,000,000、Indirect Cost: ¥2,700,000)
Keywords分子自己集合 / 超分子 / カプセル / 水素結合 / 大環状化合物 / 動的共有結合 / キラリティー / 光応答性 / 分子認識
Outline of Final Research Achievements

(1) We found that a dumbbell type pyridyl-cavitand and a dumbbell type phenol-cavitand with long flexible spacers self-assemble into a super-macrocyclic dimer (supramolecular giant ring) based on hydrogen-bonded hetero-capsule as a connector, without formation of a supramolecular polymer. (2) We found that a self-assembled boronic ester cavitand capsule encapsulates one molecule of BPEA derivatives as optical functional guests, which show greater resistance to photochemical reactions and enhancement of photophysical properties such as two-photon absorption, compared to free guests. We also found that this type of a chiral capsule induces supramolecular chirality with respect to a prochiral biphenyl guest by diastereomeric encapsulation. (3) We found the self-assembly of calix[4]resorcinarene bearing azobenzene-dendron conjugates as side chains into a hexameric capsule with photoresponsive properties that releases encapsulated guest molecule upon UV irradiation.

Report

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

    (32 results)

All 2016 2015 2014 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Acknowledgement Compliant: 5 results) Presentation (22 results) Remarks (2 results)

  • [Journal Article] Doubly Cavitand-Capped Porphyrin Capsule via Hydrogen Bonds.2016

    • Author(s)
      K. Kishimoto, M. Nakamura, K. Kobayashi
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 8 Pages: 2629-2633

    • DOI

      10.1002/chem.201504893

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Photoresponsive Self-Assembled Hexameric Capsules Based on Calix[4]resorcinarenes Bearing Azobenzene Dendron Conjugates as Side Chains.2015

    • Author(s)
      T. Sakano, T. Ohashi, M. Yamanaka, K. Kobayashi
    • Journal Title

      Org. Biomol. Chem.

      Volume: 13 Issue: 30 Pages: 8359-8364

    • DOI

      10.1039/c5ob00997a

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Self-Assembled Boronic Ester Cavitand Capsules with Various Bis(catechol)-Linkers: Cavity-Expanded and Chiral Capsules.2015

    • Author(s)
      K. Tamaki, A. Ishigami, Y. Tanaka, M. Yamanaka, K. Kobayashi
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 39 Pages: 13714-13722

    • DOI

      10.1002/chem.201501717

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Self-Aassembled Capsules Based on Tetrafunctionalized Calix[4]-resorcinarene Cavitands2015

    • Author(s)
      Kenji Kobayashi, Masamichi Yamanaka
    • Journal Title

      Chemical Society Reviews

      Volume: 44 Issue: 2 Pages: 449-466

    • DOI

      10.1039/c4cs00153b

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of a C2-Symmetrical Tetrakis(arylethynyl) Cavitand and Formation of Hybrid Hydrogen-Bonded/Metal-Ligand Coordination Supramolecular Capsules.2014

    • Author(s)
      Y. Nito, K. Nakada, K. Kobayashi, M. Yamanaka
    • Journal Title

      Asian J. Org. Chem.

      Volume: 3 Issue: 7 Pages: 762-765

    • DOI

      10.1002/ajoc.201402041

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enhanced photostability of an anthracene-based dye due to supramolecular encapsulation: A new type of photostable fluorophore for single-molecule study2014

    • Author(s)
      M. Mitsui, K. Higashi, R. Takahashi, Y. Hirumi, K. Kobayashi
    • Journal Title

      Photochemical & Photophysical Sciences

      Volume: 13 Issue: 8 Pages: 1130-1136

    • DOI

      10.1039/c4pp00065j

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Hydrogen-Bond and Metal–Ligand Coordination Bond Hybrid Supramolecular Capsules: Identification of Hemicapsular Intermediate and Dual Control of Guest Exchange Dynamics2014

    • Author(s)
      Yuki Nito, Hirofumi Adachi, Naoaki Toyoda, Hikaru Takaya, Kenji Kobayashi, Masamichi Yamanaka
    • Journal Title

      Chemistry An Asian Journal

      Volume: 9 Issue: 4 Pages: 1076-1082

    • DOI

      10.1002/asia.201301628

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photostability and One- and Two-Photon Absorption Properties of 9,10-Bis(arylethynyl)anthracene Derivatives in a Self-Assembled Boronic Ester Cavitand Capsule2014

    • Author(s)
      Y. Hirumi, K. Tamaki, T. Namikawa, K. Kamada, M. Mitsui, K. Suzuki, K. Kobayashi
    • Journal Title

      Chemistry An Asian Journal

      Volume: 9 Issue: 5 Pages: 1282-1290

    • DOI

      10.1002/asia.201400042

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] 水素結合性キャビタンドによって二重または一重にキャップされたポルフィリンカプセル2016

    • Author(s)
      中林翔・岸本和樹・小林健二
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-25
    • Related Report
      2015 Annual Research Report
  • [Presentation] 中村宗親・岸本和樹・与座健治・小林健二2016

    • Author(s)
      分子集合ギア:Rh-テトラアリールポルフィリンとテトラ(p-ピリジル)キャビタンドとの4:1錯体
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-25
    • Related Report
      2015 Annual Research Report
  • [Presentation] 水素結合ヘテロカプセルに基づく超分子ジャイアントリングとダンベル型ゲストとの分子集合2016

    • Author(s)
      梶原貴紀・小林健二
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 動的イミン結合に基づく超分子ジャイアントリングの合成2016

    • Author(s)
      藤村洸希・梶原貴紀・小林健二
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] カリックス[4]レゾルシンアレーンの分子自己集合における長鎖アルキル側鎖の影響2016

    • Author(s)
      廣田詩織・小林健二
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 超分子ジャイアントリング:ダンベル型水素結合性キャビタンドの分子自己集合2015

    • Author(s)
      梶原貴紀・岸本和樹・木下敬太・高野敦志・松下裕秀・小林健二
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋(日本大学理工学部)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 配位結合に基づく分子集合拡張型ピリジルキャビタンドカプセル2015

    • Author(s)
      中村宗親・岸本和樹・小林健二
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋(日本大学理工学部)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 四つ葉型キャビタンド:Rh-ポルフィリンとテトラ(4-ピリジル)キャビタンド誘導体との4:1分子集合体2015

    • Author(s)
      岸本和樹・小林健二
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋(日本大学理工学部)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] キラルな動的ホウ酸エステル結合キャビタンドカプセル2015

    • Author(s)
      大石歩実・玉木健斗・田中康隆・小林健二
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋(日本大学理工学部)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 光応答性分子集合カプセルにおけるデンドロン-アゾベンゼン側鎖の影響2015

    • Author(s)
      大橋俊文・坂野翼・外狩結香・小林健二
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋(日本大学理工学部)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] レスベラトロール側鎖を有するカリックス[4]レゾルシンアレーンの合成2015

    • Author(s)
      廣田詩織・大橋俊文・小林健二
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋(日本大学理工学部)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 分子カプセル化による9,10-ビス(フェニルエチニル)アントラセンの二光子吸収の増大2014

    • Author(s)
      並河知孝・蛭海洋平・玉木健斗・三井正明・小林健二・鎌田賢司
    • Organizer
      2014年光化学討論会
    • Place of Presentation
      札幌(北海道大学)
    • Year and Date
      2014-10-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] レゾルシノールポルフィリンとピリジルエチニルキャビタンドとの1:2水素結合性分子集合カプセル2014

    • Author(s)
      岸本和樹・小林健二
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      仙台(東北大学)
    • Year and Date
      2014-09-07
    • Related Report
      2014 Annual Research Report
  • [Presentation] ダンベル型キャビタンドの水素結合に基づく分子集合性巨大環状体2014

    • Author(s)
      岸本和樹・梶原貴紀・高野敦志・木下敬太・松下裕秀・小林健二
    • Organizer
      第12回ホスト・ゲスト化学シンポジウム
    • Place of Presentation
      東京(東京工業大学)
    • Year and Date
      2014-05-31
    • Related Report
      2014 Annual Research Report
  • [Presentation] Self-Assembled Boronic Ester Cavitand Capsule as a Guard Nanocontainer for Cruciform 9,10-Bis(arylethynyl)anthracene Derivatives.

    • Author(s)
      K. Kobayashi, Y. Hirumi, K. Tamaki, T. Namikawa, K. Kamada
    • Organizer
      8th International Symposium on Macrocyclic & Supramolecular Chemistry
    • Place of Presentation
      Arlington, Virginia, USA
    • Related Report
      2013 Annual Research Report
  • [Presentation] 様々なビス(カテコール)リンカーから成る動的ホウ酸エステル結合キャビタンドカプセル

    • Author(s)
      玉木健斗・小林健二
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学(東京都)
    • Related Report
      2013 Annual Research Report
  • [Presentation] アントラセン誘導体とその超分子カプセル錯体の単一分子分光:項間交差過程の不均一性の抑制と光安定性の増強

    • Author(s)
      東弘二・蛭海洋平・小林健二・三井正明
    • Organizer
      第7回分子科学討論会
    • Place of Presentation
      京都大学(京都府)
    • Related Report
      2013 Annual Research Report
  • [Presentation] アリールアゾカリックスアレーンとピリジルキャビタンドから成る水素結合性分子集合ヘテロカプセル

    • Author(s)
      大橋俊文・小林健二
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(愛知県)
    • Related Report
      2013 Annual Research Report
  • [Presentation] ダンベル型キャビタンドを基盤とする水素結合性超分子カプセル会合体の構築

    • Author(s)
      岸本和樹・梶原貴紀・高野敦志・木下敬太・山中正道・松下裕秀・小林健二
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(愛知県)
    • Related Report
      2013 Annual Research Report
  • [Presentation] レゾルシノールポルフィリンとピリジルエチニルキャビタンドから成る水素結合性分子集合カプセル

    • Author(s)
      岸本和樹・小林健二
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(愛知県)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 動的ホウ酸エステル結合に基づく分子集合カリックスアレーン

    • Author(s)
      大石歩実・玉木健斗・小林健二
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(愛知県)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 動的ホウ酸エステル結合に基づく分子集合拡張型キャビタンドカプセル

    • Author(s)
      玉木健斗・小林健二
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(愛知県)
    • Related Report
      2013 Annual Research Report
  • [Remarks] 小林研究室ホームページ

    • URL

      http://www.ipc.shizuoka.ac.jp/~skkobay/welcome.htm

    • Related Report
      2015 Annual Research Report
  • [Remarks] 小林研究室ホームページ

    • URL

      http://www.ipc.shizuoka.ac.jp/~skkobay/welcome.htm

    • Related Report
      2013 Annual Research Report

URL: 

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

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