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含カルコゲンπ共役系のトポロジー制御による新規有機半導体の開発

Research Project

Project/Area Number 20036042
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionTokyo Metropolitan University

Principal Investigator

西長 亨  Tokyo Metropolitan University, 大学院・理工学研究科, 准教授 (30281108)

Co-Investigator(Kenkyū-buntansha) 伊与田 正彦  首都大学東京, 大学院・理工学研究科, 教授 (50115995)
Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥3,800,000 (Direct Cost: ¥3,800,000)
Fiscal Year 2009: ¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 2008: ¥1,900,000 (Direct Cost: ¥1,900,000)
Keywordsカルコゲン / 反芳香族性 / 有機半導体 / トランジスター
Research Abstract

ヒュッケル則における8π電子系反芳香族化合物の代表であるシクロオクタテトラエン(COT)は、実際には非平面tub型構造をとるため環状共役せず非芳香族として振舞う。しかし、COTに平面構造を強制すると、反芳香族性を発現することが最近見い出され、平面構造のCOT誘導体には多いに興味が持たれている。これまでに我々は中央に平面性COT骨格を有するシラシクロペンタジチオフェン二量体1を合成し、その平面性COT骨格により大きな反芳香族性が誘起され、それに伴い,HOMO-LUMOギャップが著しく減少するということを明らかにしてきた。本年度はチオフェンのβ位を硫黄で架橋したジチエノチオフェン二量体についてOSi/SiO_2基板上に有機薄膜を真空蒸着により形成させ、金をソース、ドレイン電極とするトップコンタクト型の素子を作製し、半導体特性を検討した。その結果、OTS処理を施した場合に、p型のFET特性を示し、電子移動度μ=4.5×10^<-3>cm^2/Vs、I_<on>/I_<off>=10^5、閾電圧は-25Vという値を示す有機半導体であることを明らかにした。またテトラエチル体についても同様にトップコンタクト型素子を作製しFET特性を測定し、電子移動度μ=1.9×10^<-4>cm^2/Vs、I_<on>/I_<off>=50のp型半導体として振舞うことを明らかにした。

Report

(2 results)
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (24 results)

All 2010 2009 2008 Other

All Journal Article (11 results) (of which Peer Reviewed: 11 results) Presentation (9 results) Book (2 results) Remarks (2 results)

  • [Journal Article] Structural, Electronic and Magnetic Properties of Cu(II) Complexes of 2-Substituted Tropones Bearing Ferrocenyl Group at 5-Position2010

    • Author(s)
      T.Nishinaga, T.Aono, E.Isomura, S.Watanabe, Y.Miyake, A.Miyazaki, T.Enoki. H.Miyasaka. H.Otani. M.Iyoda
    • Journal Title

      Dalton Trans. 39

      Pages: 2293-2300

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Bitetrathiafulvalene with FeCl_3-Mediated Homocoupling of Tetrathiafulvalenylmagnesium Bromide and Formation of Nanostructures from Bitetrathiafulvalene having Long Alkylthio Chains2010

    • Author(s)
      Y.Honna, E.Isomura, H.Enozawa, M.Hasegawa, M.Takase, T.Nishinaga, M.Iyoda
    • Journal Title

      Tetrahedron Lett. 51

      Pages: 679-682

    • Related Report
      2009 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)
      T.Ohmae, T.Nishinaga, W,Mo, M.Iyoda
    • Journal Title

      J.Am.Chem.Soc. 132

      Pages: 1066-1074

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Recent Studies on the Aromaticity and Antiaromaticity of Planar Cyclooctatetraene2010

    • Author(s)
      T.Nishinaga, T.Ohmae, M.Iyoda
    • Journal Title

      Symmetry 2

      Pages: 76-97

    • Related Report
      2009 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)
      T.Nishinaga, D.Yamazaki, M.Tateno, M.Iyoda, K.Komatsu
    • Journal Title

      Materials 3

      Pages: 2037-2052

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Small Difference in Side Chain of Tetrathiafulvaleno[18]annulenes Causing Magnetic Alignment in Solid State and Temperature Hysteresis in Aqueous Tetrahydrofuran Solution2009

    • Author(s)
      H.Enozawa, M.Hasegawa, E.Isomura, T.Nishinaga, T.Kato, M.Yamato, T.Kimura, Masahiko Iyoda
    • Journal Title

      Chem.Phys.Chem. 10

      Pages: 2607-2611

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Thiophene-Pyrrole Mixed Oligomers End-Capped with. Hexyl Group for Field-Effect Transistors2009

    • Author(s)
      Mika Fujii, Tohru Nishinaga, Maiahiko Iyoda
    • Journal Title

      Tetrahedron Lett 50

      Pages: 555-558

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dynamic Molecular Tweezers Composed of Dibenzocyclooctatetraene Units ; Synthesis, Properties, and Thermochromism in Host-Guest Complexes2009

    • Author(s)
      Tomohiko Nishiuchi, Yoshiyuki Kuwatani, Tohru Nishinaga, Masahiko Iyoda
    • Journal Title

      Chem. Eur. J. 15(in press)

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of Cyclic [5]meta-Phenyleneacetylene and Its Corresponding Cyclophane Polyone, [25](1, 3)Cyclophanedecaone2008

    • Author(s)
      Jun Yamakawa, Masanori Ohkoshi, Futoshi, Takahashi, Tomohiko Nishiuchi, Yoshiyuki, Kuwatani, Tohru Nishinaga, Masato Yoshida, Masahiko Iyoda
    • Journal Title

      Chem. Lett 37

      Pages: 784-785

    • NAID

      130004425222

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Nonaphenylenes and Dodecaphenylenes Using Electron-Transter Oxidation of Lipshutz Cuprates and Formation of Nanostructural Materials from Hexadodecvloxvnonaphenylene2008

    • Author(s)
      M. Jalilur Rahman, Jun Yamakawa, Aoi Matsumoto, Hideo Enozawa, Tohru Nishinaga, Kenii Kamada, Masahiko Iyoda
    • Journal Title

      J. Org. Chem 73

      Pages: 5542-5548

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Long-distance ferromagnetic coupling through spin polarization in a linear heterotrinuclear iron(111)-copper(II)-iron(III) complex derived from 5-fenoceny1-2-arninotropone2008

    • Author(s)
      Yoshihiro Miyake, Sayaka Watanabe, Satoshi Aono, Tohru Nishinaga, Akira Miyazaki, Toshiaki Enoki, Hitoshi Mivasaka, Hiroyuki Otani, Masahiko Iyoda
    • Journal Title

      Chem. Commun

      Pages: 6167-6169

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] 皮芳香環を有する環状チオフェン4量体の誘導体の合成とFET特性2010

    • Author(s)
      大前武士、西長亨、高瀬雅祥、伊与田正彦、小林宣仁、功刀義人
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪
    • Year and Date
      2010-03-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] 反芳香環を有するチオアルキル置換ジチエノチオフェン2量体の合成と性質2010

    • Author(s)
      野澤優斗、大前武士、西長亨、高瀬雅祥、伊与田正彦
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪
    • Year and Date
      2010-03-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] 反芳香環を有する環状オリゴチオフェンの構造-物性相関と有機半導体への展開2010

    • Author(s)
      西長亨
    • Organizer
      特定領域研究「元素相乗系」第5回公開シンポジウム
    • Place of Presentation
      宇治
    • Year and Date
      2010-03-08
    • Related Report
      2009 Annual Research Report
  • [Presentation] 環状8π電子系を有するジチエノチオフェン2量体のFET特性2009

    • Author(s)
      大前武士、西長亨、高瀬雅祥、伊与田正彦、小林宣仁、猪狩光章、功刀義人
    • Organizer
      第36回有機典型元素化学討論会
    • Place of Presentation
      鳥取
    • Year and Date
      2009-12-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] Synthesis and Properties of Sulfur Bridged Cyclic Tetrathiophene Bearing an Antiaromatic Cyclooctatetraene Ring2009

    • Author(s)
      Takeshi Ohmae, Tohru Nishinaga, Masahiko Iyoda
    • Organizer
      13^<th> International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Luxembourg
    • Year and Date
      2009-07-20
    • Related Report
      2009 Annual Research Report
  • [Presentation] 共役8n電子系を有する環状オリゴチオフェン4量体の構造と反芳香族性2009

    • Author(s)
      大前武士、西長亨、伊与田正彦
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋
    • Related Report
      2008 Annual Research Report
  • [Presentation] A Planar Sulfur-Bridged Cyclic Tetrathiophene Bearing an An tiaromatic Cyclooctatetraene Ring2008

    • Author(s)
      Takeshi Ohmae, Tohru Nishinaga, Masahiko Iyoda
    • Organizer
      23rd International Symposium on the Org anic Chemistry of Sulfur
    • Place of Presentation
      Moscow
    • Related Report
      2008 Annual Research Report
  • [Presentation] 中央に平面性シクロオクタテトラエン構造を有する環状チオフェン4量体の合成と性質2008

    • Author(s)
      大前武士、西長亨、伊与田正彦
    • Organizer
      日本化学会第2回関東支部大会
    • Place of Presentation
      桐生
    • Related Report
      2008 Annual Research Report
  • [Presentation] ケイ素、硫黄で架橋された環状オリゴチオフェン4量体の構造と物性2008

    • Author(s)
      大前武士、西長亨、伊与田正彦
    • Organizer
      第35回有機典型元素化学討論会
    • Place of Presentation
      八王子
    • Related Report
      2008 Annual Research Report
  • [Book] "Cyclooctatetraenes" In Houben-Weyl Methods of Molecular Transformations : Compounds with All-Carbon Functions : Monocyclic Arenes, Quasiarenes, and Annulenes2008

    • Author(s)
      Tohru Nishinaga
    • Total Pages
      24
    • Publisher
      Georg Thieme Verlag
    • Related Report
      2008 Annual Research Report
  • [Book] "Nine-Membered and Higher Annulenes and Related Ions" In Houben-Weyl Methods of Molecular Transformations : Compounds with All-Carbon Functions : Monocyclic Arenes, Quasiarenes, and Annulenes2008

    • Author(s)
      Tohru Nishinaga
    • Total Pages
      22
    • Publisher
      Georg Thieme Verlag
    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://www.sci.metro-u.ac.jp/chem/org/

    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://www.sci.metro-u.ac.jp/chem/org/

    • Related Report
      2008 Annual Research Report

URL: 

Published: 2008-04-01   Modified: 2018-03-28  

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