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DEVELOPMENT OF LONG DISTANCE CARRIER-TRANSPORT SYSTEMS BASED ON THE SYNTHESIS OF EXTENSIVELY CONJUGATED SULFUR-CONTAINING HETEROARONIATICS

Research Project

Project/Area Number 12440180
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionHIROSHIMA UNIVERSITY

Principal Investigator

ASO Yoshio  Hiroshima University, Graduate School of Engineering, Associate Professor, 大学院・工学研究科, 助教授 (60151065)

Co-Investigator(Kenkyū-buntansha) TAKIMIYA Kazuo  Hiroshima University, Graduate School of Engineering, Assistant, 大学院・工学研究科, 助手 (40263735)
Project Period (FY) 2000 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥12,000,000 (Direct Cost: ¥12,000,000)
Fiscal Year 2002: ¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 2001: ¥5,500,000 (Direct Cost: ¥5,500,000)
Fiscal Year 2000: ¥4,900,000 (Direct Cost: ¥4,900,000)
KeywordsMolecular Wires / Oligothiophenes / Monodispersed Oligomers / Tripodal Rigid Anchor / Self-assembled Monolayer / Photovoltaic Devices / Fullerenes / Organic EL Materials / ボール型複素多環芳香族 / 焦電性 / テルピリジン / 拡張共役分子 / 有機EL素子 / 分子コイル / 光誘起電子移動 / 電界発光素子 / 発光材料 / 複素多環芳香族
Research Abstract

1. A series of extraordinarily long oligothiophenes up to the 96-mer has been developed by taking advantage of selective iterative couplings of the completely β-blocked sexithiophene at the terminal α-positions. Their spectroscopic measurements evidently indicate that they are highly conjugated like non-substituted oligothiophene and exhibit no convergent limit for the extended conjugation up to the 96-mer yet, which is much longer than that previously speculated for polythiophenes.
2. [60]Fullerene-linked quarter- and octi-thiophenes bearing a tripodal rigid anchor have been synthesized as components of highly efficient SAM-based photovoltaic cells. It has been demonstrated that the tripodal anchor plays an important role in preparing a well-organized SAM on a gold electrode, leading to marked enhancement of the photocurrent generation as compared to the reference system with a one-armed anchor. The highest quantum yield was estimated based on the number of absorbed photons to be 35% f … More or the octithiophene-based cell. The remarkably large quantum yield indicates that the long oligotbiophene chain can facilitate the generation and charge transport of photocurrent.
3. Oligothiophene/fullerene dyads (nT-C60) are incorporated in photovoltaic cells, which demonstrate relatively high incident photon-to-current efficiency up to 9.7 %. The generation of high photocurrents is ascribable to the ready photoinduced charge separation of the dyads and a good oligothiophene network for hole transport. The monochromatic power conversion efficiency of the A1/16T-C60/Au device measured at 456 nm is 0.4%.
4. Ter- and quater-thiophenes bearing pyrenes at the terminal α or β positions have been synthesized as novel emitting materials in organic electroluminescence devices. The efficient single layer EL devices of these compounds are fabricated by use of an Al/ultrathin LiF bilayer cathode. One of them exhibits a maximum luminance of 1860 cd/m^2 and a luminous efficiency of 0.15 lm/W, which are of the highest performance class among single-organic-layer EL devices. Less

Report

(4 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • Research Products

    (58 results)

All Other

All Publications (58 results)

  • [Publications] D.Hirayama: "Preparation and Photoelectrochemical Properties of Gold Electrodes Modified with [60]Fullerene-Linked Oligothiophenes"Chem. Lett.. 570-571 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Fujitsuka: "Solvent Polarity Dependence of Photoinduced Charge Separation in a Tetrathiophene-C_<60> Dyad Studied by Pico-and Nanosecond Laser Flash Photolysis in the Near-IR Region"J. Phys. Chem. A. 104. 4876-4881 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Kaikawa: "Synthesis and Spectroscopic Properties of [2.2]Quinquethiophenophane as an Ideal π-Dimer Model"Org. Lett. 2. 4197-4199 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Y.Aso: "Synthesis of Pyrene-Bearing Oligothiophenes as Novel Light Emitting Materials and Their Application to Single-Organic-Layer Electroluminescence Devices"Chem. Lett.. 420-421 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] N.Sumi: "Synthesis and Properties of a Series of the Longest Oligothiophenes up to the 48-Mer"Bull. Chem. Soc. Jpn.. 74. 979-988 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Y.Obara: "Synthesis and Photophysical Properties of [60]Fullerene-Oligo(thienylene-ethynylene) Dyads"Tetrahedron Lett.. 42. 6877-6881 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T.Otsubo: "Synthesis, Optical, and Conductive Properties of Long Oligothiophenes and Their Utilization as Molecular Wires"Bull. Chem. Soc. Jpn.. 74. 1789-1801 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M.Fujitsuka: "Photoinduced Charge Separation and Recombination Processes in Fine Particles of Oligothiophene-C_<60> Dyad Molecules"J. Phys. Chem. B. 105. 9930-9934 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 安蘇 芳雄: "ナノスケールオリゴチオフェンの合成と物性:導電性ポリマーモデルから分子エレクトロニクス材料へ"有機合成化学協会誌. 60. 52-61 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] D.Hirayama: "Large Photocurrent Generation of Gold Electrodes Modified with [60]Fullerene-Linked Oligothiophenes Bearing a Tripodal Rigid Anchor"J. Am. Chem. Soc.. 124. 532-533 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] J.Ikemoto: "Porphyrin-Oligothiophene-Fullerene Triads as an Efficient Intramolecular Electron-Transfer System"Org. Lett.. 4. 309-311 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K.Inouchi: "Oligo(octithienylene-diethynylene)s as Unprecedentedly Long Conjugated Nanomolecules"Org. Lett.. 4. 2533-2536 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T.Otsubo: "Functional Oligothiophenes as Advanced Molecular Electronic Materials"J. Mater. Chem.. 12. 2565-2575 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] N.Negishi: "Oligothiophene/fullerene Dyads as Active Photovoltaic Materials"Chem. Lett.. 32. 404-405 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T.Izumi: "Synthesis and Spectroscopic Properties of a Series of β-Blocked Long Oligothiophenes up to the 96-mer : Revaluation of Effective Conjugation Length"J. Am. Chem. Soc.. 125. 5286-5287 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] D. Hirayama: "Preparation and Photoelectrochemical Properties of Gold Electrodes Modified with [60]Fullerene-Linked Oligothiophenes"Chem. Lett.. 570-571 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Fujitsuka: "Solvent Polarity Dependence of Photoinduced Charge Separation in a Tetrathiophene-C_<60> Dyad Studied by Pico- and Nanosecond Laser Flash Photolysis in the Near-IR Region"J.Phys. Chem. A. 104. 4876-4881 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K. Kaikawa: "Synthesis and Spectroscopic Properties of [2,2]Quinquethiophenopliane as an Ideal π-Dimer Model"Org. Lett. 2. 4197-4199 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Y. ASO: "Synthesis of Pyrene-Bearing Oligothiophenes as Novel Light Emitting Materials and Their Application to Single-Organic-Layer Electroluminescence Devices"Chem. Lett.. 420-421 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] N. Sumi: "Synthesis and Properties of a Series of the Longest Oligothiophenes up to the 48-Mer"Bull. Chem. Soc. Jpn.. 74. 979-988 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Y. Obara: "Synthesis and Photophysical Properties of [60]Fullerene-Oligo(thienylene-ethynylene) Dyads"Tetrahedron Lett.. 42. 6877-6881 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T. Otsubo: "Synthesis, Optical, and Conductive Properties of Long Oligothiophenes and Their Utilization as Molecular Wires"Bull. Chem. Soc. Jpn.. 74. 1789-1801 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] M. Fujitsuka: "Photoinduced Charge Separation and Recombination Processes in Fine Particles of Oligothiophene-C_<60> Dyad Molecules"J. Phys. Chem. B. 105. 9930-9934 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Y. Aso: "Synthesis and Properties of Nano-Scale Oligothiophenes: From Conducting-Polymer Models to Materials for Molecular Electronics"J. Syn. Org, Chem. Jpn.. 60. 52-61 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] D. Hirayama: "Large Photocurreat Generation of Gold Electrodes Modified with [60]Fullerene-Linked Oligothiophenes Bearing a Tripodal Rigid Anchor"J. Am. Chem. Soc.. 124. 532-533 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] J. Ikemoto: "Porphyrin-Oligothiophene-Fullerene Triads as an Efficient Intramolecular Electron-Transfer System"Org. Lett.. 4. 309-311 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] K. Inouchi: "Oligo(octithienylene-diethynylene)s as Unprecedentedly Long Conjugated Nanomolecules"Org. Lett.. 4. 2533-2536 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T. Otsubo: "Functional Oligothiophenes as Advanced Molecular Electronic Materials."J. Mater. Chem.. 12. 2565-2575 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] N. Negishi: "Oligothiophene/fullerene Dyads as Active Photovoltaic Materials"Chem. Lett.. 32. 404-405 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T. Izumi: "Synthesis and Spectroscopic Properties of a Series of β-Blocked Long Oligothiophenes up to the 96-mer: Revaluation of Effective Conjugation Length"J. Am. Chem. Soc.. 125. 5286-5287 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] J.Ikemoto: "Porphyrin-Oligothiophene-Fullerene Triads as an Efficient Intramolecular Electron-Transfer System"Organic Letters. 4・3. 309-311 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.Aso: "Synthesis and Properties of Coil-Shaped 2,3-Thienylene-Ethynylene Oligomers"Molecular Crystals Liquid Crystals. 376. 153-158 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Takimiya: "Synthetic Procedure for Various Selenium-Containing Electron Donors of the Bis(Ethylenedithio)tetrathiafulvalene (BEDT-TTF) Type"Journal of the Organic Chemistry. 67・12. 4218-4227 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Takimiya: "Synthesis and Properties of Selenium Containing dmit-type Complexes"Molecular Crystals Liquid Crystals. 379. 65-70 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Inouchi: "Oligo (octithienylene-diethynylene)s as Unprecedentedly Long Conjugated Nanomolecules"Organic Letters. 4・15. 2533-2536 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] L.Zhu: "Enhanced Hole lnjection in Organic Light-emitting Diodes Consisting of Self-Assembled Monolayer of Tripod-Shaped p-Conjugated Thiols"Journal of Materials Chemistry. 12・8. 2250-2254 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Takimiya: "Synthesis, Structures, and Properties of Two Isomeric Naphthodithiophenes and Their Methyl, Methylthio, and 2-Thienyl Derivatives ; Application to Conductive Charge-Transfer Complexes and Low-Bandgap Polymers"Bulletin of the Chemical Society, Japan. 75・8. 1795-1805 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Otsubo: "Functional Oligothiophenes as Advanced Molecular electronic materials"Journal of Materials Chemistry. 12・9. 2565-2575 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.Kunugi: "Oragenic Field-Effect Transistors Using Di(2-thienyl)naphthodithiophenes as Active Layers"Chemistry Letters. 10. 958-959 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.Kunugi: "Organic Field-Effect Transistor Using Oligoselenophene as an Active Layer"Chemistry Materials. 15・1. 6-7 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] S.Sadaike: "TTF-porphyrin dyads as novel photoinduced electron transfer systems"Tetrahedron Letters. 44・1. 161-165 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] H.Nakanishi: "Spectral Properties of the Longest Oligothiophenes in the Oxidation States"Synthetic Metals. 119・1. 413-414 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] M.Fujitsuka: "Pico-and Nano-second Laser Flash Photolysis Study on Photoinduced Charge Separation in Oligothiophene-C_<60> Dyad Molecules"Research on Chemical Intermediates. 27・1. 73-88 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Y.Aso: "Synthesis of Pyrene-Bearing Oligothiophenes as Novel Light Emitting Materials and Their Application to Single-Organic-Layer Electroluminescenece Devices"Chemistry Letters. ・5. 420-421 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] N.Sumi: "Synthesis and Properties of a Series of the Longest Oligothiophenes up to the 48-Mer"Bulletin of the Chemical Society of Japan. 74・5. 979-988 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] L.Zhu: "Electrochemical Properties of Self-Assembled Monolayers of Tripod-Shaped Molecules and Their Applications to Organic Light-Emitting Diodes"Chemical Communications. ・18. 1830-1831 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Y.Obara: "Synthesis and Photophysical Properties of [60]Fullerene-Oligo (thienylene-ethynylene) Dyads"Tetrahedron Letters. 42・39. 6877-6881 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] M.Fujitsuka: "Photoinduced Charge Separation and Recombination Processes in Fine Particles of Oligothiophene-C_<60> Dyad Molecules"The Journal of Physical Chemistry B. 105・41. 9930-9934 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T.Otsubo: "Synthesis, Optical, and Conductive Properties of Long Oligothiophenes and Their Utilization as Molecular Wires"Bulletin of the Chemical Society of Japan. 74・10. 1789-1801 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 安蘇芳雄: "ナノスケールオリゴチオフェンの合成と物性:導電性ポリマーモデルから分子エレクトロニクス材料へ"有機合成化学協会誌. 60・1. 52-61 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] D.Hirayama: "Large Photocurrent Generation of Gold Electrodes Modified with [60]Fullerene-Linked Oligothiophenes Bearing a Tripodal Rigid Anchor"Journal of the American Chemical Society. 124・4. 532-533 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] J.Ikemoto: "Porphyrin-Oligothiophene-Fullerene Triads as an Efficient Intramolecular Electron-Transfer System"Organic Letters. 4・3. 309-311 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Shinobu Inoue: "Syntheses, Spectroscopic Properties, and Polymerizations of 2, 2'-Bitellurophene, 2, 2' : 5', 2"-Tertellurophene, and Related Hybrid Terchalcogenophenes"Heterocycles. 52・1. 159-170 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Daigo Hirayama: "Preparation and Photoelectrochemical Properties of Gold Electrodes Modified with [60] Fullerene-Linked Oligothiophenes"Chemistry Letters. ・5. 570-571 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Mamoru Fujitsuka: "Solvent Polarity Dependence of Photoinduced Charge Separation in a Tetrathiophene-C_<60> Dyad Studied by Pico-and Nanosecond Laser Flash Photolysis in the Near-IR Region "The Journal of Physical Chemistry A. 104・21. 4876-4881 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Takeshi Kaikawa: "Synthesis and Spectroscopic Properties of [2.2] Quinquethiophenophane as an Ideal π-Dimer Model"0rganic Letters. 2・26. 4197-4199 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] 岡井隆: "ビス[4-(N,N-ジ-p-トリルアミノ)フェニル]=カルコゲニド-カルコゲン原子を有する新しい正孔輸送材料の開発と有機EL素子への応用"日本化学会誌. ・8. 567-570 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] 大坪徹夫: "導電性オリゴチオフェン:ナノスケール分子ワイヤーの単一分子合成法"ファインケミカル. 29・10. 5-11 (2000)

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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