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Transition state analysis of [2+2] cycloaddition-retroelectrocyclization

Research Project

Project/Area Number 15KT0140
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section特設分野
Research Field Transition State Control
Research InstitutionTokyo Institute of Technology

Principal Investigator

Michinobu Tsuyoshi  東京工業大学, 物質理工学院, 准教授 (80421410)

Project Period (FY) 2015-07-10 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsクリックケミストリー / [2+2]付加環化 / ドナーアクセプター構造
Outline of Final Research Achievements

Click chemistry is a highly efficient addition reaction. In this study, [2+2] cycloaddition-retroelectrocyclization between electron-rich alkynes and electron-deficient alkenes was investigated. Reaction mechanism and product structures were studied in terms of the steric and electronic factors of the reactants. Also, the donor-acceptor products showed potent redox activities and intense charge-transfer bands. These features were successfully applied to thin film devices, such as photovoltaic cells, and specific metal ion sensors.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (20 results)

All 2018 2017 2016 2015 Other

All Journal Article (7 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 7 results,  Open Access: 2 results,  Acknowledgement Compliant: 4 results) Presentation (9 results) (of which Int'l Joint Research: 7 results,  Invited: 6 results) Book (2 results) Remarks (2 results)

  • [Journal Article] The [2+2] Cycloaddition-Retroelectrocyclization (CA-RE) Click Reaction: Facile Access to Molecular and Polymeric Push-Pull Chromophores2018

    • Author(s)
      T. Michinobu, F. Diederich
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 57 Issue: 14 Pages: 3552-3557

    • DOI

      10.1002/anie.201711605

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Colorimetric Ion Sensors Based on Polystyrenes Bearing Side Chain Triazole and Donor–Acceptor Chromophores2017

    • Author(s)
      Y. Li, Y. Washino, T. Hyakutake, T. Michinobu
    • Journal Title

      Analytical Sciences

      Volume: 33 Issue: 5 Pages: 599-604

    • DOI

      10.2116/analsci.33.599

    • NAID

      130006777383

    • ISSN
      0910-6340, 1348-2246
    • Related Report
      2017 Annual Research Report 2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Polymeric Chemosensors: A Conventional Platform with New Click Chemistry2017

    • Author(s)
      Y. Wang, T. Michinobu
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 90 Issue: 12 Pages: 1388-1400

    • DOI

      10.1246/bcsj.20170294

    • NAID

      130006250393

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Side-Chain Engineering of Polyphenylacetylene Derivatives for Tuning the Self-Assembly and Gas Permeability Properties2017

    • Author(s)
      Y. Li, H. Fujita, T. Hyakutake, T. Michinobu
    • Journal Title

      Journal of Fiber Science and Technology

      Volume: 73 Issue: 4 Pages: 82-86

    • DOI

      10.2115/fiberst.2017-0011

    • NAID

      130005562233

    • ISSN
      2189-7654
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis of Novel Polymeric Energy Materials with High Nitrogen Content by Double Click Functionalization2016

    • Author(s)
      T. Michinobu, Y. Yoshitake
    • Journal Title

      Sci. Technol. Energ. Mater.

      Volume: 77 Pages: 86-90

    • NAID

      40020915813

    • Related Report
      2016 Research-status Report 2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Cross-Linking and Postfunctionalization of Polymer Films by Utilizing the Orthogonal Reactivity of 7,7,8,8-Tetracyanoquinodimethane2016

    • Author(s)
      Y. Washino, T. Michinobu
    • Journal Title

      Phys. Chem. Chem. Phys.

      Volume: 18 Issue: 4 Pages: 2288-2291

    • DOI

      10.1039/c5cp05180k

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Sequentially Different AB Diblock and ABA Triblock Copolymers as P3HT:PCBM Interfacial Compatibilizers for BHJ Photovoltaics2016

    • Author(s)
      H. Fujita, T. Michinobu, S. Fukuda, T. Koganezawa, T. Higashihara
    • Journal Title

      ACS Appl. Mater. Interfaces

      Volume: 8 Issue: 8 Pages: 5484-5492

    • DOI

      10.1021/acsami.5b12437

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Supramolecular Materiasl by Macromolecular Silver Ion Complexes2017

    • Author(s)
      T. Michinobu
    • Organizer
      IUPAC 17th International Symposium on MacroMolecular Complexes (MMC-17)
    • Place of Presentation
      Waseda University, Tokyo
    • Year and Date
      2017-08-28
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Chiral Induction from Troger’s Base into Twisted 1,1,4,4-Tetracyanobuta-1,3-dienes (TCBDs)2017

    • Author(s)
      W. Li, T. Michinobu
    • Organizer
      Chirality 2017
    • Place of Presentation
      Waseda University, Tokyo
    • Year and Date
      2017-07-09
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] クリック反応を利用した新しい高窒素含有エネルギーポリマーの合成研究2017

    • Author(s)
      道信 剛志
    • Organizer
      火薬学会2017年度春季研究発表会
    • Related Report
      2017 Annual Research Report 2016 Research-status Report
    • Invited
  • [Presentation] New Design and Thin Film Transistor Applications of N-Type Semiconducting Polymers2017

    • Author(s)
      T. Michinobu
    • Organizer
      ICMAT 2017
    • Related Report
      2017 Annual Research Report 2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Chiral Induction from Troeger’s Base into Twisted 1,1,4,4-Tetracyanobuta-1,3-dienes (TCBDs)2017

    • Author(s)
      W. Li, T. Michinobu
    • Organizer
      Chirality 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Supramolecular Materials by Macromolecular Silver Ion Complexes2017

    • Author(s)
      T. Michinobu
    • Organizer
      IUPAC 17th International Symposium on MacroMolecular Complexes (MMC-17)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 発光型ひび割れ検出塗膜の気体透過性と検出感度に関する検討2016

    • Author(s)
      百武 壮、西崎 到、新田 弘之、道信 剛志
    • Organizer
      土木学会平成28年度全国大会第71回年次学術講演会
    • Place of Presentation
      東北大学
    • Year and Date
      2016-09-07
    • Related Report
      2016 Research-status Report
  • [Presentation] Novel Design and Thin Film Device Applications of n-Type Semiconducting Polymers2016

    • Author(s)
      T. Michinobu
    • Organizer
      The 7th International Symposium on Polymer Chemistry
    • Place of Presentation
      Changchun, China
    • Year and Date
      2016-09-07
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] New Redox-Active Multilayer Thin Films and Their Silver Complexes by Alkyne-Acceptor Click Chemistry2015

    • Author(s)
      T. Michinobu
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (Pacifichem 2015)
    • Place of Presentation
      Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Book] Encyclopedia of Polymer Applications2018

    • Author(s)
      T. Michinobu, Y. Wang
    • Publisher
      Taylor & Francis
    • Related Report
      2017 Annual Research Report
  • [Book] Organometallics and Related Molecules for Energy Conversion2015

    • Author(s)
      T. Michinobu
    • Publisher
      Springer
    • Related Report
      2015 Research-status Report
  • [Remarks] 東京工業大学 道信研究室

    • URL

      http://www.op.titech.ac.jp/lab/michinobu/jp/index.html

    • Related Report
      2017 Annual Research Report 2016 Research-status Report
  • [Remarks] 東京工業大学 道信研究室

    • URL

      http://www.op.titech.ac.jp/lab/michinobu/jp/index.html

    • Related Report
      2015 Research-status Report

URL: 

Published: 2015-07-14   Modified: 2019-03-29  

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