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Synthesis and functionalization of multilayered [3.3]cyclophanes

Research Project

Project/Area Number 25410050
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionOita University

Principal Investigator

Shibahara Masahiko  大分大学, 教育福祉科学部, 教授 (60253762)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsシクロファン / 渡環π電子相互作用 / 分子ワイヤー / 色素増感剤 / パラシクロファン
Outline of Final Research Achievements

I examined the synthesis of multilayered [3.3]para and metacyclophanes to perform a systematic study on the transannular π-electronic interaction by both through-space and/or through-bond electronic interactions.
In addition, in the donor (D) -bridge (B)- acceptor (A) systems that incorporated [3.3]cyclophanes, I succeeded the synthesis of all four possible isomers of dibromo[3.3]paracyclophanes, i.e., pseudogeminal, pseudoortho, pseudometa, and pseudopara isomers. In the [3.3]metacyclophane systems, I succeeded the synthesis of three- and four-layered dibromo[3.3]metacyclophanes, and incorporated the acceptor (naphthalimide) and the donor (carbazole) moieties into both ends benzene rings.

Report

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

    (25 results)

All 2016 2015 2014 2013 Other

All Int'l Joint Research (1 results) Journal Article (7 results) (of which Peer Reviewed: 7 results,  Acknowledgement Compliant: 4 results,  Open Access: 1 results) Presentation (16 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results) Book (1 results)

  • [Int'l Joint Research] 東海大学/台湾中央研究院(台湾)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Synthesis of Dibromo[3.3]paracyclophanes2016

    • Author(s)
      Masahiko Shibahara, Motonori Watanabe, Takaaki Miyazaki, Kenta Goto, Taisuke Matsumoto, Teruo Shinmyozu
    • Journal Title

      Synthesis

      Volume: 48 Issue: 08 Pages: 1197-1201

    • DOI

      10.1055/s-0035-1560421

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and electronic properties of ferrocene-containing organic dyads2015

    • Author(s)
      Motonori Watanabe,* Yuan Jay Chang, Po-ting Chou, Aleksandar Staykov, Masahiko Shibahara, Katsuya Sako, Tatsumi Ishihara, Tahsin J Chow
    • Journal Title

      Tetrahedron Letteers

      Volume: 56 Issue: 12 Pages: 1548-1551

    • DOI

      10.1016/j.tetlet.2015.02.012

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Crystal structure of a four-layered [3.3](3,5)pyridinophane2014

    • Author(s)
      Masahiko Shibahara, Motonori Watanabe, Taisuke Matsumoto, Kenta Goto, and Teruo Shinmyozu
    • Journal Title

      Acta Crystallographica Section E

      Volume: E70 Issue: 11 Pages: 447-450

    • DOI

      10.1107/s1600536814023691

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Structural properties of five- and six-layered [3.3]metacyclophanes2014

    • Author(s)
      Masahiko Shibahara, Motonori Watanabe, Kenta Goto, Takaaki Miyazaki, Hua Zhang, Yuki Nakayama, and Teruo Shinmyozu
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 51 Pages: 7089-7093

    • DOI

      10.1016/j.tetlet.2014.10.151

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Electronic and Photophysical Properties of [2.2]- and [3.3]Paracyclophane-Based Donor-Donor′-Acceptor Triads2014

    • Author(s)
      Takaaki Miyazaki, Masahiko Shibahara, Jun-ichi Fujishige, Motonori Watanabe, Kenta Goto, and Teruo Shinmyozu
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 79 Issue: 23 Pages: 11440-11453

    • DOI

      10.1021/jo5020273

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Four-layered [3.3]metacyclophane with ethenetetracarbonitrile2014

    • Author(s)
      Masahiko Shibahara, Motonori Watanabe, Kenta Goto, and Teruo Shinmyozu
    • Journal Title

      Acta Crystallographica Section E

      Volume: E70 Issue: 5 Pages: o625-o626

    • DOI

      10.1107/s1600536814009362

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Physical Properties, and Structure of TIPS-Difuranoacenes2014

    • Author(s)
      Watanabe, M.; Chien, C-T.; Lin, Y-D.; Chang Y. J.; Wen, Y-S.; Goto, K.; Shibahara, M.; Shinmyozu, T.; Chow, T. J
    • Journal Title

      Tetrahedron Lett

      Volume: 55 Issue: 8 Pages: 1424-1427

    • DOI

      10.1016/j.tetlet.2014.01.036

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthetic study of Donor-Bridge-Acceptor triad with three-layered [3.3]cyclophanes as bridge2016

    • Author(s)
      芝原雅彦,渡邊源規,宮﨑隆聡,新名主輝男
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] [3.3]シクロファンを架橋部位に組み込んだドナー・ブリッジ・アクセプター分子の合成研究2015

    • Author(s)
      芝原雅彦,渡邊源規,宮﨑隆聡,五島健太,新名主輝男
    • Organizer
      第9回有機π電子系シンポジウム
    • Place of Presentation
      レイクサイド入鹿(愛知県犬山市)
    • Year and Date
      2015-11-20
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis and Functionalization of Multilayered [3.3]Cyclophanes2015

    • Author(s)
      芝原雅彦,渡邊源規,五島健太,宮﨑隆聡,新名主輝男
    • Organizer
      International Symposium on Construction and Application of Functional Molecules/Systems
    • Place of Presentation
      Hotel Royal Chiaohsi in Taiwan
    • Year and Date
      2015-10-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 多層[3.3]シクロファンの合成と機能化に向けて2015

    • Author(s)
      芝原雅彦,渡邊源規,宮﨑隆聡,五島健太,新名主輝男
    • Organizer
      第5回物質・デバイス領域共同研究拠点報告会
    • Place of Presentation
      九州大学伊都キャンパス(福岡県福岡市)
    • Year and Date
      2015-04-20
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis and Structural Properties of Dibromo[3.3]paracyclophanes2015

    • Author(s)
      芝原雅彦,渡邊源規,五島健太,新名主輝男
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 多層[3.3]シクロファンの合成と物性2015

    • Author(s)
      芝原雅彦,渡邊源規,五島健太,新名主輝男
    • Organizer
      シクロファン及びパイ電子系分子の新しい化学 に関するシンポジウム
    • Place of Presentation
      九州大学大学 50 周年記念講堂(福岡県福岡市)
    • Year and Date
      2015-03-06
    • Related Report
      2014 Research-status Report
  • [Presentation] 新規アセン類の合成とデバイスへの展開2015

    • Author(s)
      渡邊源規,土井康嵩,萩原英久,伊田進太郎,五島健太,芝原雅彦,新名主輝男,周大新,石原達己
    • Organizer
      シクロファン及びパイ電子系分子の新しい化学 に関するシンポジウム
    • Place of Presentation
      九州大学大学 50 周年記念講堂(福岡県福岡市)
    • Year and Date
      2015-03-06
    • Related Report
      2014 Research-status Report
  • [Presentation] ジブロモ[3.3]パラシクロファンの合成と構造2014

    • Author(s)
      芝原雅彦,渡邊源規,宮﨑隆聡,五島健太,松本泰昌,新名主輝男
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学川内北キャンパス(宮城県仙台市)
    • Year and Date
      2014-09-08
    • Related Report
      2014 Research-status Report
  • [Presentation] [2.2]パラシクロファンをブリッジとした非共役型光誘起電荷移動分子の合成と物性2014

    • Author(s)
      宮崎隆聡,藤重隼一,芝原雅彦,五島健太,藤塚守,真嶋哲朗,新名主輝男
    • Organizer
      日本化学会第94春季年会(2014)
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] ジフラノアセン類の合成,物性と構造2014

    • Author(s)
      渡邊源規,五島健太,芝原雅彦,新名主輝男,周大新
    • Organizer
      日本化学会第94春季年会(2014)
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] パラシクロファンをブリッジとした非共役型光誘起電荷移動の機構に関する考察2013

    • Author(s)
      宮崎隆聡,藤重隼一,芝原雅彦,五島健太,新名主輝男
    • Organizer
      第50回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Related Report
      2013 Research-status Report
  • [Presentation] A Study on Photoinduced Chrge Transfer through [2.2]Paracyclophane Bridge2013

    • Author(s)
      Takaaki Miyazaki, Jun-ichi Fujishige, Masahiko Shibahara, Kenta Goto, and Teruo Shinmyozu
    • Organizer
      15th International Symposium on Novel Aromatic Compounds, Taipei
    • Place of Presentation
      Howard Civil Service International House, Taipei, Taiwan
    • Related Report
      2013 Research-status Report
  • [Presentation] Structural Properties of Charge-Transfer Complexes of Multilayered [3.3]Cyclophanes2013

    • Author(s)
      Masahiko Shibahara, Motonori Watanabe, Kenta Goto, and Teruo Shinmyozu
    • Organizer
      15th International Symposium on Novel Aromatic Compounds, Taipei
    • Place of Presentation
      Howard Civil Service International House, Taipei, Taiwan
    • Related Report
      2013 Research-status Report
  • [Presentation] パラシクロファンをブリッジとした非共役型光誘起電荷移動分子の合成と物性2013

    • Author(s)
      宮崎隆聡,藤重隼一,芝原雅彦,五島健太,藤塚守,真嶋哲朗,新名主輝男
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学目白キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] TIPS基を有する高次ジフラノアセンの合成と物性2013

    • Author(s)
      渡邊源規,簡敬庭,林彦多,聞昱生,張源杰,五島健太,芝原雅彦,新名主輝男,周大新
    • Organizer
      第7回有機π電子系シンポジウム
    • Place of Presentation
      高崎ビューホテル
    • Related Report
      2013 Research-status Report
  • [Presentation] [2.2]パラシクロファンをブリッジとした非共役型光誘起電荷移動分子の開発2013

    • Author(s)
      宮崎隆聡,藤重隼一,芝原雅彦,五島健太,藤塚守,真嶋哲朗,新名主輝男
    • Organizer
      第7回有機π電子系シンポジウム
    • Place of Presentation
      高崎ビューホテル
    • Related Report
      2013 Research-status Report
  • [Book] Organic Structures Design - Applications in Optical and Electronic Devices2014

    • Author(s)
      Masahiko Shibahara, Motonori Watanabe, Takaaki Miyazaki, Jun-ichi Fujishige, Yuki Matsunaga, Keisuke Tao, Zhang Hua, Kenta Goto, and Teruo Shinmyozu
    • Total Pages
      538
    • Publisher
      Pan Stanford Publishing
    • Related Report
      2014 Research-status Report

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Published: 2014-07-25   Modified: 2022-02-01  

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