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Development of novel construction and multifunctional properties of organic supramolecular nanoassembly

Research Project

Project/Area Number 22245024
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials chemistry
Research InstitutionTokyo Metropolitan University

Principal Investigator

IYODA Masahiko  首都大学東京, 公私立大学の部局等, 特任教授 (50115995)

Co-Investigator(Kenkyū-buntansha) TAKASE Masayoshi  首都大学東京, 大学院理工学研究科, 助教 (90516121)
HASEGAWA Masashi  北里大学, 理学部, 講師 (20438120)
OTANI Hiroyuki  横浜国立大学, 大学院環境情報研究院, 教授 (30213763)
Co-Investigator(Renkei-kenkyūsha) SHIMIZU Hideyuki  首都大学東京, 大学院理工学研究科, 特任研究員 (10727697)
Project Period (FY) 2010-05-31 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥43,810,000 (Direct Cost: ¥33,700,000、Indirect Cost: ¥10,110,000)
Fiscal Year 2013: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2012: ¥6,240,000 (Direct Cost: ¥4,800,000、Indirect Cost: ¥1,440,000)
Fiscal Year 2011: ¥14,300,000 (Direct Cost: ¥11,000,000、Indirect Cost: ¥3,300,000)
Fiscal Year 2010: ¥17,680,000 (Direct Cost: ¥13,600,000、Indirect Cost: ¥4,080,000)
Keywords超分子 / 有機π電子系 / 巨大環状分子 / ナノ集積体 / モルフォロジー / ナノファイバー / 複合機能 / 分子スイッチ / 有機巨大分子 / 巨大π電子系 / 分子導線 / 量子細線
Outline of Final Research Achievements

In this project, we have developed a new concept for the construction of organic supramolecular nanoassembly and prepared key organic pi-electron systems for the studies on their multifunctional properties. We have successfully synthesized a series of giant conjugated macrocycles and constructed their self-assembled nanostructures. The most remarkable properties were obtained from pi-expanded macrocyclic oligothiophene 6-mer and 8-mer. The 6-mer showed a thermally reversible polymorphism, which was applied to either fluorescence switching or switching of field effect transistor (FET) activity and electrical conductivity. The 8-mer formed a Saturn-like complex with C60 in the solid state, and this complex exhibited repeatable and stable instantaneous response of photocurrent.

Report

(5 results)
  • 2014 Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (40 results)

All 2014 2013 2012 2010 Other

All Journal Article (24 results) (of which Peer Reviewed: 24 results) Presentation (9 results) (of which Invited: 6 results) Book (3 results) Remarks (4 results)

  • [Journal Article] Additive Electron Pathway and Non-additive Molecular Conductance by Using a Multipodal Bridging Compound2014

    • Author(s)
      M. Kiguchi, Y. Takahashi, S. Fujii, M. Takase, T. Narita, M. Iyoda, M. Horikawa, Y. Naitoh, H. Nakamura
    • Journal Title

      J. Phys. Chem. C

      Volume: 118 Issue: 10 Pages: 5275-5283

    • DOI

      10.1021/jp4100262

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Multifunctional π-Expanded Macrocyclic Oligothiophene 6-Mers and Related Macrocyclic Oligomers2014

    • Author(s)
      Iyoda, M.; Tanaka, K.; Shimizu, H.; Hasegawa, M.; Nishinaga, T.; Nishiuchi, T.; Kunugi, Y.; Ishida, T.; Otani, H.; Sato, H.; Inukai, K.; Tahara, K.; Tobe, Y.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 136 Issue: 6 Pages: 2389-2396

    • DOI

      10.1021/ja4101744

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effect of Substituents on the Structure, Stability, and pi-Dimerization of Dithienylpyrrole Radical Cations2013

    • Author(s)
      T. Nishinaga, T. Kageyama, M. Koizumi, K. Ando, M. Takase, M. Iyoda
    • Journal Title

      J. Org. Chem.

      Volume: 78 Issue: 18 Pages: 9205-9213

    • DOI

      10.1021/jo401453s

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Pentadecaphenylenes, Its Inclusion Properties, and Nanostructure Formation with C602013

    • Author(s)
      M. J. Rahman, H. Shimizu, Y. Araki, H. Ikeda, M. Iyoda
    • Journal Title

      Chem. Commun.

      Volume: 49 Issue: 81 Pages: 9251-9253

    • DOI

      10.1039/c3cc42922a

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structure-dependent Electronic Natures of Star-shaped Oligothiophenes Probed by Ensemble and Single-molecule Spectroscopy2013

    • Author(s)
      H. Chung, T. Narita, J. Yang, P. Kim, M. Takase, M. Iyoda, D. Kim
    • Journal Title

      Chem. Eur. J.

      Volume: 19 Issue: 29 Pages: 9699-9709

    • DOI

      10.1002/chem.201300313

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Antiaromatic planar cyclooctatetraene: a strategy for ambipolar semiconductors in field effect transistors2013

    • Author(s)
      T. Nishinaga, T. Ohmae, K. Aita, M. Takase, M. Iyoda, T. Arai, Y. Kunugi
    • Journal Title

      Chem. Commun.

      Volume: 49 Issue: 47 Pages: 5354-5356

    • DOI

      10.1039/c3cc41764f

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Steric Control in the pi-Dimerization of Oligothiophene Radical Cations Annelated with Bicyclo[2.2.2]octene Units2013

    • Author(s)
      M. Tateno, M. Takase, M. Iyoda, K. Komatsu, T. Nishinaga
    • Journal Title

      Chem. Eur. J.

      Volume: 19 Issue: 17 Pages: 5457-5467

    • DOI

      10.1002/chem.201204332

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solvent-induced Crystalline State Emission and Multichromism of Bent pi-Surface System Composed of Dibenzocyclooctatetraene Units2013

    • Author(s)
      T. Nishiuchi, K. Tanaka, Y. Kuwatani, J. Sung, T. Nishinaga, D. Kim, M. Iyoda
    • Journal Title

      Chem. Eur. J.

      Volume: 19 Issue: 13 Pages: 4110-4116

    • DOI

      10.1002/chem.201203952

    • Related Report
      2013 Annual Research Report 2012 Annual Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Giant Conjugated Macrocycles: Synthesis and Applications2012

    • Author(s)
      M. Iyoda
    • Journal Title

      J. Synth. Org. Chem. Jpn.

      Volume: 70 Pages: 1157-1163

    • NAID

      10031131194

    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sterically congested pyrrole-fused tetrathiafulvalene decamers as highly conductive amorphous molecular materials2012

    • Author(s)
      M. Takase
    • Journal Title

      RSC Advances

      Volume: 2 Issue: 8 Pages: 3221-3224

    • DOI

      10.1039/c2ra00035k

    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Self-Assembly, Chromic Properties, and Nanostructure Formation of Tetrathiafulvalene-Fused Dodecadehydro[18]annulenes2012

    • Author(s)
      H. Enozawa
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 85 Issue: 10 Pages: 1120-1137

    • DOI

      10.1246/bcsj.20120135

    • NAID

      10031120562

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Face-to-Face Arranged Dimeric Tetrathiafulvalenes in 1,8-Bis(tetrathiafulvalenyl)naphthalenes as a Model of Mixed Valence and π-Dimer States2012

    • Author(s)
      Masashi Hasegawa, Kota Daigoku, Kenro Hashimoto, Haruyuki Nishikawa, Masahiko Iyoda
    • Journal Title

      Bull.Chem.Soc.Jpn.

      Volume: 85 Issue: 1 Pages: 51-60

    • DOI

      10.1246/bcsj.20110224

    • NAID

      130004152985

    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cyclic Tetrathiophenes Planarized by Silicon and Sulfur Bridges Bearing Antiaromatic Cyclooctatetraene Core : Syntheses, Structures, and Properties2010

    • Author(s)
      伊與田正彦
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 132 Pages: 1066-1074

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fully Conjugated Macrocycles Composed of Thiophenes, Acetylenes, and Ethylenes2010

    • Author(s)
      伊與田正彦
    • Journal Title

      Pure Appl.Chem.

      Volume: 82 Pages: 831-841

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Conducting supramolecular nanofibers and nanorods2010

    • Author(s)
      伊與田正彦
    • Journal Title

      Chem.Soc.Rev.

      Volume: 39 Pages: 2420-2427

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and electrical conductivity of perchlorate-doped TTF diamide nanofibers2010

    • Author(s)
      伊與田正彦
    • Journal Title

      J.Mater.Chem.

      Volume: 20 Pages: 10817-10823

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Biradical Character of Linear π-Conjugated Oligomer Dications Composed of Thiophene, Pyrrole and Methylthio End-Capping Units2010

    • Author(s)
      伊與田正彦
    • Journal Title

      Org.Lett.

      Volume: 12 Pages: 5374-5377

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Shape-controllable gold nanocrystallization using an amphiphilic polythiophene2010

    • Author(s)
      伊與田正彦
    • Journal Title

      Chem.Commun.

      Volume: 46 Pages: 8603-8605

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Star-Shaped Oligothiophenes with Unique Photophysical Properties and Nanostructures2010

    • Author(s)
      伊與田正彦
    • Journal Title

      Chem.Eur.J.

      Volume: 16 Pages: 12108-12113

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An Efficient Synthesis of Chiral Isoquinuclidines by Diels-Alder Reaction Using Lewis Acid Catalyst2010

    • Author(s)
      伊與田正彦
    • Journal Title

      Tetrahedron

      Volume: 66 Pages: 7618-7624

    • NAID

      120003339540

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of Octithiophene Dication Sterically Segregated by Annelation with Bicyclo[2.2.2]octene Units2010

    • Author(s)
      伊與田正彦
    • Journal Title

      Materials

      Volume: 3 Pages: 2037-2052

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structural, electronic and magnetic properties of Cu(II) complexes of 2-substituted tropones bearing ferrocenyl group at 5-position2010

    • Author(s)
      伊與田正彦
    • Journal Title

      Dalton Trans.

      Volume: 39 Pages: 2420-2427

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and p-Amphoteric Properties of Tris(tetrathiafulvaneno)hexadehydro-[12]annulene2010

    • Author(s)
      伊與田正彦
    • Journal Title

      Heterocycles

      Volume: 80 Pages: 909-915

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of bitetrathiafulvalenes with FeCl_3-mediated homo-coupling of tetrathiafulvalenyl-magnesium chloride and molecular fiber formation form tetrakis(dodecylthio)tetrathiafulvalene2010

    • Author(s)
      伊與田正彦
    • Journal Title

      Tetrahedron Lett.

      Volume: 51 Pages: 679-682

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] Nano-sized to Giant Conjugated Macrocycles: Synthesis and Versatile Applications2013

    • Author(s)
      S. Shimizu, M. J. Rahman, M. Iyoda
    • Organizer
      ISIS-8
    • Place of Presentation
      Nara
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 機能性有機π電子系と歩む2013

    • Author(s)
      伊與田正彦
    • Organizer
      早稲田大学講演会
    • Place of Presentation
      早稲田大学
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Nanostructure Formation and Functional Properties of Macrocyclic Oligothiophene 6 and 8-mers2013

    • Author(s)
      M. Iyoda, K. Tanaka, H. Shimizu
    • Organizer
      The 15th Asian Chemical Congress
    • Place of Presentation
      Singapore
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Pentadecaphenylenes, Its Inclusion Properties, and Nanostructure Formation with C602013

    • Author(s)
      H. Shimizu, M. J. Rahman, Y. Arai, H. Ikeda, M. Iyoda
    • Organizer
      the 15th Internal Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Taipei, Taiwan
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 大環状オリゴチオフェン-合成とその特異な物性2012

    • Author(s)
      伊與田正彦
    • Organizer
      大阪府立大学白鷺セミナー第65回講演会
    • Place of Presentation
      大阪府立大学、堺
    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
    • Invited
  • [Presentation] Nanostructure Formation and Functional Properties of Giant Macrocyclic Oligothiophenes2012

    • Author(s)
      M. Iyoda
    • Organizer
      2nd International Conference on Nanotek and Expo
    • Place of Presentation
      Philadelphia, Pennsylvania, USA
    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
    • Invited
  • [Presentation] 新しい環状π電子系の構築と機能に関する研究2012

    • Author(s)
      伊與田正彦
    • Organizer
      第6回有機π電子系シンポジウム
    • Place of Presentation
      松山、愛媛
    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
  • [Presentation] Self-organization of fully conjugated macrocycles : synthesis and functional properties2010

    • Author(s)
      伊與田正彦
    • Organizer
      The 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2010-12-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] Conducting Supramolecular Nanofibers and Nanorods2010

    • Author(s)
      伊與田正彦
    • Organizer
      The 11th Eurasia Conference
    • Place of Presentation
      The dead sea, Jordan
    • Year and Date
      2010-10-11
    • Related Report
      2010 Annual Research Report
  • [Book] マテリアルステージ2013

    • Author(s)
      伊與田正彦
    • Total Pages
      6
    • Publisher
      情報技術協会
    • Related Report
      2013 Annual Research Report
  • [Book] PEDOT の材料物性とデバイス応用2012

    • Author(s)
      伊與田正彦、西長亨
    • Total Pages
      7
    • Publisher
      サイエンス&テクノロジー
    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
  • [Book] Fully Conjugated Nano-Sized Macrocycles : Syntheses and Versatile Properties2010

    • Author(s)
      伊與田正彦
    • Total Pages
      30
    • Publisher
      Wiley-VCH
    • Related Report
      2010 Annual Research Report
  • [Remarks] 伊與田研究室ホームページ

    • URL

      http://www.comp.tmu.ac.jp/iyoda/

    • Related Report
      2013 Annual Research Report
  • [Remarks] 首都大学東京伊與田研究室

    • URL

      http://www.comp.tmu.ac.jp/iyoda/

    • Related Report
      2012 Annual Research Report
  • [Remarks] 首都大学東京伊與田研究室

    • URL

      http://www.comp.tmu.ac.jp/iyoda/

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://www.comp.tmu.ac.jp/iyoda/

    • Related Report
      2010 Annual Research Report

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Published: 2010-11-30   Modified: 2019-07-29  

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