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Construction of hollow spherical particles composed of macrocycles with functional groups

Research Project

Project/Area Number 16K05801
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Polymer chemistry
Research InstitutionTokushima Bunri University

Principal Investigator

Tominaga Masahide  徳島文理大学, 薬学部, 准教授 (60361507)

Research Collaborator KATAGIRI Kosuke  甲南大学, 理工学部, 准教授 (90412395)
MASU Hyuma  千葉大学, 大学院工学研究科, 准教授 (80412394)
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2018: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords環状化合物 / 自己集合 / 球状粒子 / 分子集合体 / 動的挙動 / 相転移 / 発光特性 / 溶媒効果 / 結晶構造 / 球状ナノ粒子 / キラリティー / 中空球状ナノ粒子 / 官能基導入 / 自己組織化 / ナノ材料 / 超分子化学
Outline of Final Research Achievements

A series of adamantane-bearing macrocycles possessing diverse sizes, shapes, conformations, and functional groups were designed and synthesized. These compounds were self-assembled into hollow spherical particles, whose formation are attributed to solvophobic interactions derived from the aliphatic character of adamantane parts in macrocycles. The sizes, stabilities, and internal structures of hollow spherical particles were mostly dependent to the substituents on the macrocyclic frameworks and used solvents. The external stimuli including polarity of solvents, temperature, and guest addition caused the change of their sizes and morphologies, and phase transition from amorphous to crystalline materials. Further, the shapes and morphologies of self-assembled architectures and the introduced functional groups on macrocycles affect directly each property such as fluorescence and wettability.

Academic Significance and Societal Importance of the Research Achievements

独自の分子設計指針による多彩な形状・サイズ・機能性官能基を有する環状分子群の合成と、これを基盤とした中空球状微粒子ライブラリーの構築および機能創出に取り組んでいる研究は限られている。このようなナノからミクロンサイズの中空球状微粒子を基盤とする技術は、製薬や食品などのバイオサイエンスの分野から触媒、塗料、電池などのマテリアルサイエンスの分野まで幅広く活用できる可能性がある。得られた成果は自己組織化化学や超分子化学などのナノサイエンスの分野、特にベシクルやナノ微粒子の研究領域に有用な知見と有意な波及効果をもたらすと思われる。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (37 results)

All 2019 2018 2017 2016 Other

All Journal Article (13 results) (of which Peer Reviewed: 13 results,  Acknowledgement Compliant: 2 results) Presentation (23 results) (of which Int'l Joint Research: 2 results) Remarks (1 results)

  • [Journal Article] Co-crystal screening of disubstituted adamantane molecules with N-heterocyclic moieties for hydrogen-bonded arrays2019

    • Author(s)
      Masatoshi Kawahata*, Masahide Tominaga, Yuki Kawanishi, Kentaro Yamaguchi*
    • Journal Title

      Journal of Molecular Structure

      Volume: 1177 Pages: 511-518

    • DOI

      10.1016/j.molstruc.2018.09.093

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Self-Assembly Behavior Shifting to Crystal Formation of Chiral Macrocyclic Tetraimines2019

    • Author(s)
      Masahide Tominaga,* Masatoshi Kawahata, Tsutomu Itoh, and Kentaro Yamaguchi*
    • Journal Title

      Crystal Growth & Design

      Volume: 19 Issue: 2 Pages: 1118-1124

    • DOI

      10.1021/acs.cgd.8b01617

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cycloalkanes and cycloalkenes in dispersion force oriented inclusion crystals by a functionalized acyclic host molecule2019

    • Author(s)
      Tadashi Hyodo, Masatoshi Kawahata,* Yuya Hikami, Ai Komatsu, Masahide Tominaga and Kentaro Yamaguchi*
    • Journal Title

      CrystEngComm

      Volume: 21 Issue: 10 Pages: 1548-1554

    • DOI

      10.1039/c8ce01990h

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hollow and Solid Spheres Assembled from Functionalized Macrocycles Containing Adamantane2019

    • Author(s)
      Masahide Tominaga,* Nobuto Kunitomi, Kazuaki Ohara, Masatoshi Kawahata, Tsutomu Itoh, Kosuke Katagiri, and Kentaro Yamaguchi*
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 84 Issue: 9 Pages: 5109-5117

    • DOI

      10.1021/acs.joc.9b00069

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Separation of p-xylene from aromatic compounds through specific inclusion by acyclic host molecule2018

    • Author(s)
      Masatoshi Kawahata,* Tadashi Hyodo, Masahide Tominaga and Kentaro Yamaguchi*
    • Journal Title

      CrystEngComm

      Volume: 20 Issue: 38 Pages: 5667-5671

    • DOI

      10.1039/c8ce01101j

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Crystallization Processes through Self-Assembled Materials Dependent on the Substituents of Tetrapodal Adamantanes2018

    • Author(s)
      Masahide Tominaga,* Akitaka Iekushi, Kazuaki Ohara, Masatoshi Kawahata, Tsutomu Itoh, Kentaro Yamaguchi,* and Isao Azumaya*
    • Journal Title

      Chemistry Letters

      Volume: 47 Issue: 10 Pages: 1279-1281

    • DOI

      10.1246/cl.180572

    • NAID

      130007495975

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Inclusion and selectivity of amides by p-terphenyl derivative bearing adamantanecarboxylic acid2018

    • Author(s)
      Masatoshi Kawahata*, Kiyoe Matsui, Tadashi Hyodo, Masahide Tominaga, Kentaro Yamaguchi*
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 49 Pages: 7089-7094

    • DOI

      10.1016/j.tet.2018.10.043

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Spherical Aggregates and Crystal Structure of Naphthalenediimide-Based Macrocycle and Complexation with Perylene2018

    • Author(s)
      Masahide Tominaga, Masatoshi Kawahata, Tsutomu Itoh, and Kentaro Yamaguchi
    • Journal Title

      Crystal Growth & Design

      Volume: 18 Issue: 1 Pages: 37-41

    • DOI

      10.1021/acs.cgd.7b01361

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Crystal Formation of a Coordination Cage through Spherical Particles Derived from a Tripodal Ligand Containing Adamantane Moiety and Silver(I) Salt2018

    • Author(s)
      Masahide Tominaga, Hisanobu Ando, Kazuaki Ohara, Tsutomu Itoh, and Kentaro Yamaguchi
    • Journal Title

      Chemistry Letters

      Volume: 47 Issue: 3 Pages: 315-317

    • DOI

      10.1246/cl.171105

    • NAID

      130006434121

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Hydrogen-bonded structures from adamantane-based catechols2018

    • Author(s)
      Masatoshi Kawahata, Miku Matsuura, Masahide Tominaga, Kosuke Katagiri, Kentaro Yamaguchi
    • Journal Title

      Journal of Molecular Structure

      Volume: 1164 Pages: 116-122

    • DOI

      10.1016/j.molstruc.2018.03.011

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Preparation and crystal structure of charge-transfer complexes of acyclic host molecules bearing pyrogallol derivatives with paraquat2017

    • Author(s)
      Masatoshi Kawahata, Masahide Tominaga, Yumi Maekawa and Kentaro Yamaguchi
    • Journal Title

      CrystEngComm

      Volume: 19 Issue: 48 Pages: 7229-7235

    • DOI

      10.1039/c7ce01748k

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Solvent-Dependent Self-Assembly and Crystal Structures of a Salen-Based Macrocycle2017

    • Author(s)
      Masahide Tominaga,* Eri Takahashi, Hiroyuki Ukai, Kazuaki Ohara, Tsutomu Itoh, and Kentaro Yamaguchi*
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 7 Pages: 1508-1511

    • DOI

      10.1021/acs.orglett.7b00264

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Vesicle Formation of Three-dimensional Trinuclear Silver(I) Complexes Built from Tris-NHC Ligands Bearing Long Alkyl Chains2016

    • Author(s)
      Masahide Tominaga,* Taichi Kawaguchi, Kazuaki Ohara, Kentaro Yamaguchi, Kosuke Katagiri, Tsutomu Itoh, and Isao Azumaya*
    • Journal Title

      Chemistry Letters

      Volume: 45 Issue: 10 Pages: 1201-1203

    • DOI

      10.1246/cl.160622

    • NAID

      130005540203

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 環状化合物からなる多孔質結晶による青葉アルコールの吸着と構造解析2019

    • Author(s)
      富永昌英・川幡正俊・兵頭 直・山口健太郎
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] V型分子を活用した環式脂肪族化合物の包接と結晶構造解析2019

    • Author(s)
      川幡正俊・兵頭 直・小松 愛・氷上優也・富永昌英・山口健太郎
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] V型非環状分子と脂環式化合物との共結晶化による包接挙動解析2019

    • Author(s)
      兵頭 直・川幡正俊・氷上優也・小松 愛・富永昌英・山口健太郎
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Spherical Aggregation and Crystallization of Naphthalenediimide-Based Macrocycle bearing Adamantane Moieties2018

    • Author(s)
      富永昌英・川幡正俊・伊藤努武・山口健太郎
    • Organizer
      Asian Crystallization Technology Symposium 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 芳香族求核置換反応によるオキサシクロファンおよびその[2]カテナンの合成と結晶構造2018

    • Author(s)
      富永昌英・川幡正俊・山口健太郎
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 官能基化V型分子による脂環式化合物の包接結晶の作製と構造解析2018

    • Author(s)
      兵頭 直・川幡正俊・小松 愛・氷上優也・富永昌英・山口健太郎
    • Organizer
      第27回有機結晶シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] 非環状分子を用いた共結晶化によるp-キシレンの高選択的包接と分離2018

    • Author(s)
      兵頭 直・川幡正俊・富永昌英・山口健太郎
    • Organizer
      2018年日本化学会中国四国支部大会 愛媛大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] V型分子を活用した環状アルカンの包接と結晶構造解析2018

    • Author(s)
      氷上優也・川幡正俊・富永昌英・兵頭 直・弘瀬由香里・山口健太郎
    • Organizer
      2018年日本化学会中国四国支部大会 愛媛大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] V型分子を活用した環状アルケンの包接と結晶構造解析2018

    • Author(s)
      小松 愛・川幡正俊・富永昌英・兵頭 直・弘瀬由香里・山口健太郎
    • Organizer
      2018年日本化学会中国四国支部大会 愛媛大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 拡張V型分子を用いたゲスト包接結晶の作製と構造解析2018

    • Author(s)
      藤丸滉輔・川幡正俊・富永昌英・兵頭 直・弘瀬由香里・山口健太郎
    • Organizer
      2018年日本化学会中国四国支部大会 愛媛大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 共結晶化によるアミド化合物の包接と選択性2018

    • Author(s)
      松井貴世恵・川幡正俊・富永昌英・兵頭 直・弘瀬由香里・山口健太郎
    • Organizer
      2018年日本化学会中国四国支部大会 愛媛大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] V型非環状分子の共結晶化による石油成分の分離2018

    • Author(s)
      川幡正俊・富永昌英・兵頭 直・山口健太郎
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] キラル環状イミンの球状集合体形成と結晶化過程2018

    • Author(s)
      富永昌英・川幡正俊・伊藤努武・山口健太郎
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] V型アダマンタン分子と芳香族炭化水素の共結晶化2018

    • Author(s)
      兵頭 直・川幡正俊・富永昌英・山口健太郎
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Presentation] Self-Assembly and Crystallization of Adamantane-Based Macrocycles2017

    • Author(s)
      Masahide Tominaga, Kazuaki Ohara, Tsutomu Itoh, Kentaro Yamaguchi
    • Organizer
      8th International Conference on Advanced Materials and Nanotechnology
    • Place of Presentation
      Queenstown
    • Year and Date
      2017-02-12
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] ナフタレンジイミド骨格からなる環状分子の構築とペリレンとの会合体形成挙動2017

    • Author(s)
      富永昌英・川幡正俊・伊藤努武・山口健太郎
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 環状分子からなる中空球状集合体とマイクロチューブ2017

    • Author(s)
      富永昌英・川幡正俊・伊藤努武・山口健太郎
    • Organizer
      第66回高分子討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] V型非環状ホスト分子によるゲスト包接結晶の構築と構造解析2017

    • Author(s)
      川幡正俊・富永昌英・前川祐美・山口健太郎
    • Organizer
      第26回有機結晶シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] ヘテロ環化合物を有する二置換アダマンタンによる水素結合共結晶の構築2017

    • Author(s)
      川西佑来・川幡正俊・富永昌英・山口健太郎
    • Organizer
      2017年日本化学会中国四国支部大会鳥取大会
    • Related Report
      2017 Research-status Report
  • [Presentation] 多脚性分子を用いたパラコート包接結晶の作製と構造解析2017

    • Author(s)
      前川祐美・川幡正俊・富永昌英・山口健太郎
    • Organizer
      2017年日本化学会中国四国支部大会鳥取大会
    • Related Report
      2017 Research-status Report
  • [Presentation] サレン部位を有する環状分子の合成と溶媒に依存した自己集合と結晶化2016

    • Author(s)
      高橋英里・富永昌英・鵜飼厚行・伊藤努武・小原一朗・山口健太郎
    • Organizer
      2016年日本化学会中国四国支部大会香川大会
    • Place of Presentation
      香川大学
    • Year and Date
      2016-11-05
    • Related Report
      2016 Research-status Report
  • [Presentation] 溶媒に依存したかご型およびシート型錯体の構築と結晶化挙動2016

    • Author(s)
      富永昌英・安藤寿典・伊藤努武・小原一朗・山口健太郎
    • Organizer
      第25回有機結晶シンポジウム
    • Place of Presentation
      京都大学大学院
    • Year and Date
      2016-09-18
    • Related Report
      2016 Research-status Report
  • [Presentation] 六角形型環状分子上の置換基に依存した結晶構造と自己集合挙動2016

    • Author(s)
      富永昌英・國富寛大・伊藤努武・小原一朗・山口健太郎
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島国際会議場
    • Year and Date
      2016-09-01
    • Related Report
      2016 Research-status Report
  • [Remarks] 徳島文理大学香川薬学部解析化学講座ホームページ

    • URL

      http://kp.bunri-u.ac.jp/kph10/index.html

    • Related Report
      2018 Annual Research Report 2017 Research-status Report 2016 Research-status Report

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Published: 2016-04-21   Modified: 2020-03-30  

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