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電子構造に段差を有するナノ共役系の構築と階層制御

Research Project

Project/Area Number 19022019
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

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

Principal Investigator

安蘇 芳雄  Osaka University, 産業科学研究所, 教授 (60151065)

Co-Investigator(Kenkyū-buntansha) 家 裕隆  大阪大学, 産業科学研究所, 助教 (80362622)
Project Period (FY) 2007 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 2008: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 2007: ¥1,500,000 (Direct Cost: ¥1,500,000)
Keywordsオリゴチオフェン / 分岐型オリゴチオフェン / 光誘起分子内電荷移動 / 自己会合 / πスタック / 光電変換素子 / ペリレンビスイミド / ラジカルイオン / 分岐型オリゴチオフエン / 酸化還元電位 / 電界効果トランジスタ / フラーレン
Research Abstract

共役系の電子構造制御による多機能階層の創製を目的とした電子構造に段差を有する次世代ナノ共役系の構築として, 前年に引き続き以下の研究を遂行した。
多分岐型オリゴチオフェンが高い溶解性にもかかわらず強い自己会合特性を有し, 薄膜状態で良好な正孔キャリア移動度を示したので, 分岐構造の複数の末端に電子キャリア担体としてアルキル基の導入で溶解性が確保でき, πスタックに好都合な平面性と高いアクセプター性を有するペリレンビス(ジカルボキシイミド)ユニットの導入を行った。蛍光スペクトルではオリゴチオフェン部励起, ペリレンビスイミド部励起, いずれの場合も蛍光強度の著しい減少が観測され, 効率的な光誘起分子内電子移動を示唆している。また, ^1NMRスペクトルの濃度依存性から, 中央部が8T化合物の二量化会合定数は3387M^<-1>と高く, MALDI-TOF MSでも会合に由来するピークが観測された。スピンコート薄膜をITOとアルミニウム電極でサンドイッチした有機単層素子を作製して可視光に対する光電変換機能を評価したところ, 外部量子収率は, 分岐を持たない直鎖の比較化合物に比べて一桁以上向上して, 多分岐型に由来する薄膜での会合が大きく寄与していることが示唆された。過渡吸収-マイクロウエーブ伝導度測定では, 対応するラジカルアニオンおよびラジカルカチオン種の生成が確認され, キャリア移動度は1.3×10^<-2>cm^2V^<-1>s^<-1>の高い値が観測された。

Report

(3 results)
  • 2008 Annual Research Report
  • 2007 Annual Research Report
  • Products Report
  • Research Products

    (54 results)

All 2009 2008 2007

All Journal Article (15 results) (of which Peer Reviewed: 15 results) Presentation (28 results) Book (3 results) Patent(Industrial Property Rights) (8 results)

  • [Journal Article] Synthesis, Structure, and. Properties of 2,5,8,11,14,17-Hexamethyltriphenyleno[2,1b : 3, 4-b' : 6,5-b'' : 7, 8-b''' : 10, 9-b'''' : 11, 12-b''''']hexathiophene2009

    • Author(s)
      M. Endou
    • Journal Title

      Heterocycles 76

      Pages: 1043-1048

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dendritic Oligothiophene Bearing Perylene Bis (dicarboximide) Groups as an Active Material for Photovoltaic Device2009

    • Author(s)
      Y. Ie
    • Journal Title

      Chem. Commun 2009(印刷中)

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photovoltaic Performance and Charge Carrier Mobility of Dendritic Oligothiophene Bearing Perylene Bis (dicarboximide) Groups2009

    • Author(s)
      Y. Ie
    • Journal Title

      Synth. Metals (印刷中)

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dendritic Oligothiophene Bearing Perylene Bis (dicarboximide) Groups as an Active Material for Photovoltaic Device2009

    • Author(s)
      Y. le
    • Journal Title

      Chem. Commun.

      Volume: 2009 Pages: 1213-1215

    • Related Report
      Products Report
    • Peer Reviewed
  • [Journal Article] Electronegative Oligothiophenes Fully Annelated with Hexafluorocyclopentene : Synthesis, Properties, and Intrinsic Electron Mobility2008

    • Author(s)
      Y. Umemoto
    • Journal Title

      Org. Lett 10

      Pages: 1095-1098

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Perfluoroalkyl-Annelated Conjugated Systems towards n-Type Organic Semiconductors2008

    • Author(s)
      Y. Ie
    • Journal Title

      Pure Appl. Chem 80

      Pages: 589-597

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of Electron-Transporting Conjugated Oligomers Based on Fluorination Reactions and Their Application to Organic Field-Effect Transistors2008

    • Author(s)
      Y. Ie
    • Journal Title

      J. Syn. Org. Chem. Jpn 66

      Pages: 504-514

    • NAID

      10021175239

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electronegative Oligothiophenes Based on Difluorodioxocyclopentene-Annelated Thiophenes: Synthesis, Properties, and n-Type FET Performances2008

    • Author(s)
      Y., le
    • Journal Title

      Org. Lett. 10

      Pages: 833-836

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Substrate Effect of STM-Induced Luminesece from Porphyrih Molecules2008

    • Author(s)
      H.W., Liu
    • Journal Title

      Thin Solid Films 516

      Pages: 2727-2730

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electronegative oligothiophenes Fully Annelated with Hexafluorocyclopentene: Synthesis,Properties, and Intrinsic Electron Mobility2008

    • Author(s)
      y., Umemoto
    • Journal Title

      Org. Lett. 10(印刷中)

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Perfluoroalkyl-Annelated Conjugated Systems towards n-Type Organic Semiconductors2008

    • Author(s)
      Y. le
    • Journal Title

      Pure Appl. Chem. 80(印刷中)

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ambipolar Characteristics of Dendritic Oligothiophene/Fullerene Linkage Molecules2007

    • Author(s)
      N., Negishi
    • Journal Title

      Chem. Lett. 36

      Pages: 544-545

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electronegative Oligothiophenes for n-Type Semiconductors: Difluoromethylene-Bridged Bithiophene and Its Oligomers2007

    • Author(s)
      Y., le
    • Journal Title

      Org. Lett. 9

      Pages: 2115-2118

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Polaron Dynamics in two Types of Long Olgothiophenes Revealed by Q-and X-Band ESR Measurements2007

    • Author(s)
      K., Kanemoto
    • Journal Title

      Phys. Rev. B 76

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Properties, and Structures of Difluoromethylene-bridged Coplanarp-Terphenyl and Its Aryl-capped Derivatives for electron-transporting Materials2007

    • Author(s)
      Y., le
    • Journal Title

      Chem. Lett. 36

      Pages: 1326-1327

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] Synthesis, Properties, and Photovoltaic Performances of Branched Oligothiophenes Bearing Naphthalene Bis (dicarboximide) Groups2009

    • Author(s)
      Yutaka Ie
    • Organizer
      Fifth International Conference on Molecular Electronics and Bioelectronics (M&BE5)
    • Place of Presentation
      Miyazaki
    • Year and Date
      2009-03-17
    • Related Report
      Products Report
  • [Presentation] Synthesis and Properties of Branched Oligothiophenes Bearing Perylene Bis (dicarboximide) Groups2009

    • Author(s)
      T. Uto
    • Organizer
      The 12th SANKEN International Symposium
    • Place of Presentation
      Osaka Univ.
    • Year and Date
      2009-01-22
    • Related Report
      Products Report
  • [Presentation] 様々な官能基を有する三脚型アンカーユニットの合成と単分子膜の評価2008

    • Author(s)
      廣瀬智哉
    • Organizer
      第2回有機π電子系シンポジウム
    • Place of Presentation
      広島市
    • Year and Date
      2008-12-05
    • Related Report
      2008 Annual Research Report
  • [Presentation] アクセプター部位としてペリレンビスイミド基を持つ分岐型オリゴチオフェンの合成と物性2008

    • Author(s)
      宇都俊彦
    • Organizer
      第2回有機π電子系シンポジウム
    • Place of Presentation
      広島市
    • Year and Date
      2008-12-05
    • Related Report
      2008 Annual Research Report
  • [Presentation] Difluorodioxocyclopentene-Annelated Thiophenes : Synthesis, Properties, and n-Type FET Performances2008

    • Author(s)
      Yutaka Ie
    • Organizer
      18th Iketani Conference, International Conference on Control of Super-Hierarchical Structures and Innovative Functions of Next-Generation Conjugated Polymers
    • Place of Presentation
      淡路島夢舞台国際会議場
    • Year and Date
      2008-10-21
    • Related Report
      2008 Annual Research Report
  • [Presentation] Synthesis and Properties of. Branched Oligothiophenes Having Perylene Bisimide Groups as an Electron-Accepting Unit2008

    • Author(s)
      Toshihiko Uto
    • Organizer
      18th Iketani Conference, International Conference on Control of Super-Hierarchical Structures and Innovative Functions of Next-Generation Conjugated Polymers
    • Place of Presentation
      淡路島夢舞台国際会議場
    • Year and Date
      2008-10-21
    • Related Report
      2008 Annual Research Report
  • [Presentation] アクセプターを導入した分岐型オリゴチオフェンの合成と物性2008

    • Author(s)
      宇都俊彦
    • Organizer
      第19回基礎有機化学討論会
    • Place of Presentation
      大阪大学吹田キャンパス
    • Year and Date
      2008-10-03
    • Related Report
      2008 Annual Research Report
  • [Presentation] チオフェン縮環トリフェニレン誘導体の合成、構造、および物性2008

    • Author(s)
      遠藤克
    • Organizer
      第19回基礎有機化学討論会
    • Place of Presentation
      大阪大学吹田キャンパス
    • Year and Date
      2008-10-03
    • Related Report
      2008 Annual Research Report
  • [Presentation] Synthesis and Photovoltaic Performance of Branched Oligothiophenes Having Perylene Bis(dicarboximide)2008

    • Author(s)
      Toshihiko Uto
    • Organizer
      The Fifth International Symposium on Integrated Synthe sis (ISIS-5)
    • Place of Presentation
      神戸市舞子
    • Year and Date
      2008-09-06
    • Related Report
      2008 Annual Research Report
  • [Presentation] Synthesis, Structure, and Properties of 2, 5, 8, 11, 14, 17-Hexamethyltriphenyleno [2, 1-b : 3, 4-b' : 6, 5-b'' : 7, 8-b''' : 10, 9-b'''' : 11, 12-b''''']hexathiophene2008

    • Author(s)
      Masaru Endou
    • Organizer
      LXII Yamada Conference 2008 "Topological Molecules"
    • Place of Presentation
      淡路島夢舞台国際会議場
    • Year and Date
      2008-09-03
    • Related Report
      2008 Annual Research Report
  • [Presentation] Synthesis, Properties, and n-Type FET Performances of Difluorodioxocyclopentene-annelated Oligomers2008

    • Author(s)
      Yutaka Ie
    • Organizer
      LXII Yamada Conference 2008 "Topological Molecules"
    • Place of Presentation
      淡路島夢舞台国際会議場
    • Year and Date
      2008-09-03
    • Related Report
      2008 Annual Research Report
  • [Presentation] Synthesis, Properties, and n-Type FET Performances of Difluorodioxocyclopentene-annelated Oligothiophenes2008

    • Author(s)
      Yutaka Ie
    • Organizer
      The 8th International Symposium on Functional pi-Electr on Systems (Fpi8)
    • Place of Presentation
      Graz, Austria
    • Year and Date
      2008-07-24
    • Related Report
      2008 Annual Research Report
  • [Presentation] ア久セナター部位としてペリレンビスイミド基を導入した分岐型オリゴチオフェンの合成と物性2008

    • Author(s)
      宇都俊彦
    • Organizer
      日本化学会第88 春季年会(2008)
    • Place of Presentation
      池袋 立教大学
    • Year and Date
      2008-03-28
    • Related Report
      2007 Annual Research Report
  • [Presentation] ヘキサフルオロシクロペンタ[C]チオフェン6量体:還元種のスペクトルと薄膜の電子移動度2008

    • Author(s)
      梅本欽一
    • Organizer
      日本化学会第88 春季年会(2008)
    • Place of Presentation
      池袋 立教大学
    • Year and Date
      2008-03-28
    • Related Report
      2007 Annual Research Report
  • [Presentation] ジフルオロジオキソシクロペシテン縮環を導入した電子受容性オリゴチオフェンの合成・物性とFET,特性評価2008

    • Author(s)
      岡部 誠
    • Organizer
      日本化学会第88 春季年会(2008)
    • Place of Presentation
      池袋 立教大学
    • Year and Date
      2008-03-28
    • Related Report
      2007 Annual Research Report
  • [Presentation] 力ルボ二架橋型ビチアゾーを用いたオリゴマーの合成・物性とFET特性2008

    • Author(s)
      二谷 真司
    • Organizer
      日本化学会第88 春季年会(2008)
    • Place of Presentation
      池袋 立教大学
    • Year and Date
      2008-03-28
    • Related Report
      2007 Annual Research Report
  • [Presentation] セレン官能基を有する三脚型アンガーユニットの合成とその単分子膜の評価2007

    • Author(s)
      廣瀬智哉
    • Organizer
      第 34 回有機典型元素化学討論会
    • Place of Presentation
      吹田市大阪大學
    • Year and Date
      2007-12-13
    • Related Report
      2007 Annual Research Report
  • [Presentation] 金属電極との接合部位にセレン官能基を有する三脚型アンカーユニットの開発2007

    • Author(s)
      廣瀬 智哉
    • Organizer
      第 37 回構造有機化学討論会
    • Place of Presentation
      札幌市北海道大学
    • Year and Date
      2007-10-29
    • Related Report
      2007 Annual Research Report
  • [Presentation] 末端にカルポニル基を有する電子受容性オリゴマーの合成と物性及びFET評価2007

    • Author(s)
      二谷 真司
    • Organizer
      第 37 回構造有機化学討論会
    • Place of Presentation
      札幌市北海道大学
    • Year and Date
      2007-10-29
    • Related Report
      2007 Annual Research Report
  • [Presentation] 被覆型オリゴチオフェンの開発と被覆効果の化学的評価2007

    • Author(s)
      遠藤 克
    • Organizer
      第 37 回構造有機化学討論会
    • Place of Presentation
      札幌市北海道大学
    • Year and Date
      2007-10-27
    • Related Report
      2007 Annual Research Report
  • [Presentation] オリゴチオフェンーフラーレン連結分子の機能2007

    • Author(s)
      安蘇芳雄
    • Organizer
      日本化学会 第1 回関東支部大会(2007)
    • Place of Presentation
      八王子市首都大学東京
    • Year and Date
      2007-09-28
    • Related Report
      2007 Annual Research Report
  • [Presentation] n型有機半導体を指向したフルオ自アルキル架矯オリゴチオフ土ンの開発2007

    • Author(s)
      家 裕隆
    • Organizer
      第56回高分子討論会
    • Place of Presentation
      名古屋市名古屋工業大学
    • Year and Date
      2007-09-21
    • Related Report
      2007 Annual Research Report
  • [Presentation] Synthesis and Electronics Application of Modified Oligothiophenes2007

    • Author(s)
      Y, Aso
    • Organizer
      Post-Symposium of ISNA in Himeji/Harima on Functional Aromatic Compounds
    • Place of Presentation
      兵庫播磨
    • Year and Date
      2007-07-30
    • Related Report
      2007 Annual Research Report
  • [Presentation] Fluoroalkyl-Annelated Conjugated Oligomers as n-Type Organic Semiconductors2007

    • Author(s)
      Y, Aso
    • Organizer
      12th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      淡路島夢舞台国際会議場
    • Year and Date
      2007-07-25
    • Related Report
      2007 Annual Research Report
  • [Presentation] Synthesis and Properties of Cyclic Conjugated Oligomers having Benzothiophenes for Linkage Unit2007

    • Author(s)
      T, Hirose
    • Organizer
      12th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      淡路島夢舞台国際会議場
    • Year and Date
      2007-07-23
    • Related Report
      2007 Annual Research Report
  • [Presentation] Synthesis and Properties of Conjugated Oligomers Containing Prerfluoroalkyl-bridged Terphenyl2007

    • Author(s)
      M, Nitani
    • Organizer
      12th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      淡路島夢舞台国際会議場
    • Year and Date
      2007-07-23
    • Related Report
      2007 Annual Research Report
  • [Presentation] Synthesis of 10-nm Scale Oligothiophen Molecular Wires Bearing Anchor Units at both Terminal Positions2007

    • Author(s)
      M, Endou
    • Organizer
      12th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      淡路島夢舞台国際会議場
    • Year and Date
      2007-07-23
    • Related Report
      2007 Annual Research Report
  • [Presentation] Thieno[3,2-d]imidazolium-containing Molecular Wire: Switching Behaviro of Photoinduced Intramolecular Electron Transfer2007

    • Author(s)
      Y, Ie
    • Organizer
      12th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      淡路島夢舞台国際会議場
    • Year and Date
      2007-07-23
    • Related Report
      2007 Annual Research Report
  • [Book] 次世代共役ポリマーの超階層制御と革新機能「電荷輸送制御のための多分岐共役系階層構造構築と機能」2009

    • Author(s)
      安蘇芳雄
    • Publisher
      シーエムシー出版
    • Related Report
      Products Report
  • [Book] 電子共役系有機材料の創製・機能開発・応用2008

    • Author(s)
      安蘇芳雄, 家 裕隆
    • Publisher
      シーエムシー出版
    • Related Report
      2007 Annual Research Report
  • [Book] ナノカーポンハンドプック2007

    • Author(s)
      安蘇芳雄, 家 裕隆
    • Publisher
      エヌ・ティー・エス
    • Related Report
      2007 Annual Research Report
  • [Patent(Industrial Property Rights)] 含窒素縮合環化合物, 含窒素縮合環重合体,有機薄膜及び有機薄膜素子2008

    • Inventor(s)
      家裕隆, 二谷真司, 安蘇芳雄, 上田将人
    • Industrial Property Rights Holder
      大阪大学・住友化学株式会社
    • Industrial Property Number
      2008-220031
    • Filing Date
      2008-08-28
    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] 分岐型化合物,これを用いた有機薄膜及び有機薄膜素子2008

    • Inventor(s)
      家裕隆, 宇都俊彦, 安蘇芳雄, 上田将人
    • Industrial Property Rights Holder
      大阪大学・住友化学株式会社
    • Industrial Property Number
      2008-221779
    • Filing Date
      2008-08-29
    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] 共役系化合物, 並びにこれを用いた有機薄膜及び有機薄膜素子2008

    • Inventor(s)
      家裕隆, 安蘇芳雄, 岡部誠, 上田将人
    • Industrial Property Rights Holder
      大阪大学・住友化学株式会社
    • Industrial Property Number
      2008-290027
    • Filing Date
      2008-11-12
    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] 共役系化合物, 含窒素縮合環化合物, 含窒素縮合環重合体, 有機薄膜及び有機薄膜素子2008

    • Inventor(s)
      安蘇芳雄, 家裕隆, 岡部誠, 二谷真司, 上田将人
    • Industrial Property Rights Holder
      大阪大学・住友化学株式会社
    • Filing Date
      2008-11-27
    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] 含窒素縮合環化合物, 含窒素縮合環重合体, 有機薄膜及び有機膜素子2008

    • Inventor(s)
      家 裕隆, 安藤芳雄, 岡部 誠, 上田将人
    • Industrial Property Rights Holder
      大阪大学・住友化学株式会社
    • Filing Date
      2008-02-13
    • Related Report
      2007 Annual Research Report
  • [Patent(Industrial Property Rights)] 分岐型化合物、これを用いた有機薄膜及び有機薄膜素子2008

    • Inventor(s)
      家 裕隆, 安藤芳雄, 岡部 誠, 上田将人
    • Industrial Property Rights Holder
      大阪大学・住友化学株式会社
    • Filing Date
      2008-02-13
    • Related Report
      2007 Annual Research Report
  • [Patent(Industrial Property Rights)] 重合体、これを用いた有機薄膜及び有機薄膜素子2008

    • Inventor(s)
      辛川 誠, 安藤芳雄, 上田将人
    • Industrial Property Rights Holder
      大阪大学・住友化学株式会社
    • Filing Date
      2008-02-13
    • Related Report
      2007 Annual Research Report
  • [Patent(Industrial Property Rights)] 共役系化合物、並びにこれを用いた有機薄膜及び有機薄膜素子2007

    • Inventor(s)
      家 裕隆, 安藤芳雄, 岡部 誠, 上田将人
    • Industrial Property Rights Holder
      大阪大学・住友化学株式会社
    • Filing Date
      2007-11-30
    • Related Report
      2007 Annual Research Report

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Published: 2007-04-01   Modified: 2018-03-28  

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