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Development of a novel synthetic system for preparation of pi-conjugated oligomers

Research Project

Project/Area Number 15K13691
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionYokohama National University

Principal Investigator

Atobe Mahito  横浜国立大学, 大学院環境情報研究院, 教授 (90291351)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords反応場 / マイクロリアクター / 電解合成
Outline of Final Research Achievements

Oligothiophenes have been used in many high-technological applications including OLEDs, OFETs and OPVs. However, their synthesis is usually required complicated multi-step processes and toxic transition metal catalysts.
On the other hand, the integrated use of microflow technology for organic electrosynthesis would offer one of the most sophisticated processes in organic chemistry. In the present work, we have successfully developed the novel electrosynthetic system for the preparation of oligothiophenes without their deposition using a flow microreactor. Molecular weight and its distribution of oligothiophenes could be controlled by selecting the reaction conditions.

Report

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

    (34 results)

All 2017 2016 2015 Other

All Journal Article (14 results) (of which Peer Reviewed: 12 results,  Open Access: 2 results,  Acknowledgement Compliant: 7 results) Presentation (18 results) (of which Int'l Joint Research: 17 results,  Invited: 4 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer Pathway2017

    • Author(s)
      Yang QU, Hiroyuki TATENO, Yoshimasa MATSUMURA, Tsuneo KASHIWAGI, Mahito ATOBE
    • Journal Title

      Molecules

      Volume: 22 Issue: 3 Pages: 413-422

    • DOI

      10.3390/molecules22030413

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] In Situ Generation of Trichloromethyl Anion and Efficient Reaction with Benzaldehyde in an Electrochemical Flow Microreactor2016

    • Author(s)
      Yoshimasa MATSUMURA, Yoshiyuki YAMAJI, Hiroyuki TATENO, Tsuneo KASHIWAGI, Mahito ATOBE
    • Journal Title

      Chem. Lett.

      Volume: 45 Issue: 7 Pages: 816-818

    • DOI

      10.1246/cl.160337

    • NAID

      130005253012

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Electrocatalytic Hydrogenation of Toluene Using a Proton Exchange Membrane Reactor2016

    • Author(s)
      Ken TAKANO, Hiroyuki TATENO, Yoshimasa MATSUMURA, Atsushi FUKAZAWA, Tsuneo KASHIWAGI, Koji NAKABAYASHI, Kensaku NAGASAWA, Shigenori MITSUSHIMA, Mahito ATOBE
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 89 Issue: 10 Pages: 1178-1183

    • DOI

      10.1246/bcsj.20160165

    • NAID

      130006770664

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electrochemical Polymerization on Porous Electrodes in Neat and Highly Concentrated Monomer Solutions2016

    • Author(s)
      Eisaku TANAKA, Hiroyuki TATENO, Yoshimasa MATSUMURA, Koji NAKABAYASHI, Mahito ATOBE
    • Journal Title

      Chem. Lett.

      Volume: 45 Issue: 11 Pages: 1271-1273

    • DOI

      10.1246/cl.160627

    • NAID

      130005509435

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electrocatalytic Hydrogenation of <i>o</i>-Xylene in a PEM Reactor as a Study of a Model Reaction for Hydrogen Storage2016

    • Author(s)
      Ken TAKANO, Hiroyuki TATENO, Yoshimasa MATSUMURA, Atsushi FUKAZAWA, Tsuneo KASHIWAGI, Koji NAKABAYASHI, Kensaku NAGASAWA, Shigenori MITSUSHIMA, Mahito ATOBE
    • Journal Title

      Chemistry Letters

      Volume: 45 Issue: 12 Pages: 1437-1439

    • DOI

      10.1246/cl.160766

    • NAID

      130005475733

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Electroresponsive Structurally Colored Materials from a Combination of Structural and Electrochromic Color Effects2016

    • Author(s)
      Tomoya KUNO, Yoshimasa MATSUMURA, Koji NAKABAYASHI, Mahito ATOBE
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 7 Pages: 2503-2506

    • DOI

      10.1002/anie.201511191

    • Related Report
      2016 Annual Research Report 2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] フローマイクロリアクターを利用する有機電解合成システムの開発2016

    • Author(s)
      松村吉将,跡部真人
    • Journal Title

      ケミカルエンジニアリング

      Volume: 61 Pages: 693-701

    • Related Report
      2016 Annual Research Report
  • [Journal Article] 有機電解合成の最近の動向2016

    • Author(s)
      跡部真人
    • Journal Title

      触媒

      Volume: 58 Pages: 357-361

    • NAID

      40021034736

    • Related Report
      2016 Annual Research Report
  • [Journal Article] Continuous In Situ Electrogenaration of 2-Pyrrolidone Anion in Microreactor: Application to Highly Efficient Monoalkylation of Methyl Phenylacetate2015

    • Author(s)
      Yoshimasa MATSUMURA, Yoshinobu KAKIZAKI, Hiroyuki TATENO, Tsuneo KASHIWAGI, Yoshiyuki YAMAJI, Mahito ATOBE
    • Journal Title

      RSC Advances

      Volume: 5 Issue: 117 Pages: 96851-96854

    • DOI

      10.1039/c5ra19286b

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Development of a Novel Electrochemical Carboxylation System Using a Microreactor2015

    • Author(s)
      Hiroyuki TATENO, Yoshimasa MATSUMURA, Koji NAKABAYASHI, Hisanori SENBOKU, Mahito ATOBE
    • Journal Title

      RSC Advances

      Volume: 5 Issue: 119 Pages: 98721-98723

    • DOI

      10.1039/c5ra19289g

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Spherical Polymer Nanoparticles Reflecting Size of Monomer Droplets Formed by Tandem Acoustic Emulsification2015

    • Author(s)
      Yuki HIARAI, Miharu KOSHIMO, Yoshimasa MATSUMURA, Mahito ATOBE
    • Journal Title

      Chem. Lett.

      Volume: 44 Issue: 11 Pages: 1584-1585

    • DOI

      10.1246/cl.150740

    • NAID

      130005108109

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Electrochemical Fixation of CO2 to Organohalides in Room-Temperature Ionic Liquids under Supercritical CO22015

    • Author(s)
      Hiroyuki TATENO, Koji NAKABAYASHI, Tsuneo KASHIWAGI, Hisanori SENBOKU, Mahito ATOBE
    • Journal Title

      Electrochim. Acta

      Volume: 161 Pages: 212-218

    • DOI

      10.1016/j.electacta.2015.01.072

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Anodic Aromatic C,C Cross-Coupling Reaction Using Parallel Laminar Flow Mode in a Flow Microreactor2015

    • Author(s)
      Toshihiro ARAI, Hiroyuki TATENO, Koji NAKABAYASHI, Tsuneo KASHIWAGI, Mahito ATOBE
    • Journal Title

      Chem. Commun.

      Volume: 51 Issue: 23 Pages: 4891-4894

    • DOI

      10.1039/c5cc01253h

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 1.有機電解合成の現状とフローマイクロリアクターの利用2015

    • Author(s)
      跡部 真人
    • Journal Title

      Electrochemistry

      Volume: 83 Issue: 6 Pages: 463-466

    • DOI

      10.5796/electrochemistry.83.463

    • NAID

      130005074241

    • ISSN
      1344-3542, 2186-2451
    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Presentation] グリーンエレクトロケミカルプロセスの開発2017

    • Author(s)
      跡部真人
    • Organizer
      第27回グリーンケミストリーフォーラム
    • Place of Presentation
      東京
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Preparation of Soap-Free Emulsion by Using Tandem Ultrasonication and Synthesis of Size-Controlled Polymer Nanoparticles2016

    • Author(s)
      Miharu KOSHIMO, Yuki HIRAI, Yoshimasa MATSUMURA, Mahito ATOBE
    • Organizer
      The sixth Asia-Oceania Conference on Sustainable and Green Chemistry
    • Place of Presentation
      Hong Kong
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Study on Electrochemical Hydrogenation of Toluene in a PEM Reactor with Various Noble Metal Supported Catalysts2016

    • Author(s)
      Atsushi FUKAZAWA, Hiroyuki TATENO, Shigenori MITSUSHIMA, Mahito ATOBE
    • Organizer
      The sixth Asia-Oceania Conference on Sustainable and Green Chemistry
    • Place of Presentation
      Hong Kong
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Electropolymerization on Porous Electrodes in Neat and Highly Concentrated Monomer Solutions2016

    • Author(s)
      Eisaku TANAKA, Koji NAKABAYASHI, Mahito ATOBE
    • Organizer
      The sixth Asia-Oceania Conference on Sustainable and Green Chemistry
    • Place of Presentation
      Hong Kong
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Preparation of Transparent Nanoemulsion Using Tandem Acoustic Emulsification and Application to Polymer Material Synthesis2016

    • Author(s)
      Mahito ATOBE
    • Organizer
      The 10th International Symposium on Integrated Synthesis
    • Place of Presentation
      Awaji, Japan
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Efficient Diels-Alder Reaction of o-Quinone Electrogenerated in a Flow Microreator2016

    • Author(s)
      Hirona YOSHIZAWA, Hiroyuki TATENO, Mahito ATOBE
    • Organizer
      PRiME2016
    • Place of Presentation
      Honolulu, USA
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Electrochemical Polymerization of 3-Hexylthiophene Using a Flow Microreactor2016

    • Author(s)
      Masatsugu MIZUNO, Hiroyuki TATENO, Mahito ATOBE
    • Organizer
      PRiME2016
    • Place of Presentation
      Honolulu, USA
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Preparation of EDOT Monomer Nanoemulsion under Surfactant-Free Conditions Using Tandem Acoustic Emulsification and Application to Electropolymerization2016

    • Author(s)
      Mahito ATOBE, Koji NAKABAYASHI
    • Organizer
      ECAT2016
    • Place of Presentation
      Hayama, Japan
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Electrochemical hydrogenation of toluene using a PEM reactor with various noble metal supported catalysts2016

    • Author(s)
      Atsushi FUKAZAWA, Hiroyuki TATENO, Shigenori MITSUSHIMA, Mahito ATOBE
    • Organizer
      ECAT2016
    • Place of Presentation
      Hayama, Japan
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Anodic C-C Bond Forming Reactions Using Parallel Laminar Flow Mode in a Flow Microreactor2016

    • Author(s)
      Mahito ATOBE
    • Organizer
      The 2nd International Symposium on Middle Molecular Strategy (ISMMS-2)
    • Place of Presentation
      Osaka, Japan
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Cathodic Cross-Coupling Reaction of Aromatic Compounds Though SET Pathway Towards a Novel Biphenyl Synthesis2016

    • Author(s)
      Yang QU, Hiroyuki TATENO, Mahito ATOBE
    • Organizer
      229th Electrochem. Soc. Meet.
    • Place of Presentation
      San Diego, USA
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Monoalkylations of Methyl Phenylacetate Using in situ Electrogenaration of 2-Pyrrolidone Anion in an Electrochemical Flow-microreactor2016

    • Author(s)
      Yoshimasa MATSUMURA, Yoshinobu KAKIZAKI, Hiroyuki TATENO, Mahito ATOBE
    • Organizer
      229th Electrochem. Soc. Meet.
    • Place of Presentation
      San Diego, USA
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of a Novel Electrocarboxylation System Using Electrochemical Flow-microreactor2016

    • Author(s)
      Hiroyuki TATENO, Yoshimasa MATSUMURA, Koji NAKABAYASHI, Mahito ATOBE
    • Organizer
      6th German-Japanese Symposium on Electrosynthesis
    • Place of Presentation
      Kyoto, Japan
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Anodic C,C Cross-coupling Reaction of Aromatic Compounds Using Parallel Laminar Flow Mode in a Flow Microreactor2016

    • Author(s)
      Mahito ATOBE
    • Organizer
      The 12th International Symposium on Organic Reactions (ISOR-12)
    • Place of Presentation
      Kyoto, Japan
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Cathodic Cross-Coupling Reaction between Aromatic Compounds through SET Pathway Toward a Novel Biphenyl Synthesis2015

    • Author(s)
      Y. Qu, H. Tateno, M. Atobe
    • Organizer
      Yokohama Environment and Information Sciences International Forum
    • Place of Presentation
      Yokohama
    • Year and Date
      2015-12-23
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of a Novel Electrocarboxylation System Using a Flow Microreactor2015

    • Author(s)
      H. Tateno, K. Nakabayashi, M. Atobe
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Electrochemical Synthesis of Poly(3-hexylthiophene) Using a Flow Microreactor2015

    • Author(s)
      M. Mizuno, H. Tateno, M. Atobe
    • Organizer
      GSC-7 & 4th JACI/GSC Symposium
    • Place of Presentation
      Tokyo
    • Year and Date
      2015-07-07
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of a Novel Electrochemical Carboxylation System Using Flow Microreactor2015

    • Author(s)
      H. Tateno, K. Nakabayashi, M. Atobe
    • Organizer
      GSC-7 & 4th JACI/GSC Symposium
    • Place of Presentation
      Tokyo
    • Year and Date
      2015-07-07
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Remarks] 跡部研究室

    • URL

      http://www.atobe-lab.ynu.ac.jp/

    • Related Report
      2016 Annual Research Report 2015 Research-status Report
  • [Patent(Industrial Property Rights)] シス-アルケンの製造装置及び製造方法2017

    • Inventor(s)
      橋本康嗣,佐藤康司,跡部真人,深澤篤,簑島樹里
    • Industrial Property Rights Holder
      橋本康嗣,佐藤康司,跡部真人,深澤篤,簑島樹里
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2017-027125
    • Filing Date
      2017-02-16
    • Related Report
      2016 Annual Research Report

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Published: 2015-04-16   Modified: 2018-03-22  

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