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Development of Ordered Monolayer Based on the Self Assembly of Molecular Tripods

Research Project

Project/Area Number 18550124
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

KITAGAWA Toshikazu  Mie University, Graduate School of Engineering, Professor (20183791)

Co-Investigator(Kenkyū-buntansha) TAKAHASHI Yasutake  Toyama University, Graduate School of Medicine and Pharmaceutical Science for ResearchGraduate School of Engineering, Professor (70197185)
HIRAI Katsuyuki  Mie University, Life Science Research Center, Associate Professor (80208793)
Project Period (FY) 2006 – 2007
Project Status Completed (Fiscal Year 2007)
Budget Amount *help
¥4,120,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥420,000)
Fiscal Year 2007: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2006: ¥2,300,000 (Direct Cost: ¥2,300,000)
KeywordsMolecular Tripod / Self-Assembled Monolayer / Adamantane Ferrocene / Ferrocene / Thiol / Au(111)Surface / Molecular Wire / Electron Transfer Rate
Research Abstract

1) Synthesis of Molecular Tripod-Ferrocene Dyads and Their Monolayers
Dyads consisting of a molecular tripod and ferrocene, connected through oligo (phenyleneethynylene) linkers of different lengths, were synthesized. The tripod has a rigid adamantane core to which three CH_2SH legs are attached in order to enable chemisorption on gold surface. The self-assembled monolayers of these dyads were prepared on Au (111) surface and analyzed by means of electrochemical measurements. The surface densities of the monolayers were shown to be constant irrespective of the length of the linker, demonstrating that the adjacent ferrocene units are fixed with a uniform intermolecular distance due to the rigid framework of adamantane and linear linker. It was also shown that there is negligible interaction among neighboring ferrocene units. This indicates that each ferrocene unit is kept independent from adjacent molecules, suggesting that these dyads are of potential use as molecular memories.
2) Synthesis of an Extended Molecular Tripod and Its Monolayer
A new adamantane tripod, having C(CH_3)2SH groups in place of the CH_2SH groups, was synthesized. Owing to the bulkiness of the two methyl groups, each tripod molecule is expected to occupy an increased area, resulting in greater molecular distance. Reductive desorption experiments for the self-assembled monolayer on Au(111) surface of this new trithiol showed that the molecular distance is significantly wider(10.9 A) than without the methyl groups. Future synthesis of dyads of this new tripod and functional molecular units would enable formation of monolayers of large-sized functional molecules

Report

(3 results)
  • 2007 Annual Research Report   Final Research Report Summary
  • 2006 Annual Research Report
  • Research Products

    (30 results)

All 2008 2007 2006

All Journal Article (6 results) (of which Peer Reviewed: 2 results) Presentation (24 results)

  • [Journal Article] Hierarchical Chiral Framework Based on a Rigid Adamantane Tripod on Au(111)2007

    • Author(s)
      片野 諭、金 有洙、松原寛明、北川敏一、川合真紀
    • Journal Title

      Journal of the American Chemical Society 129巻

      Pages: 2511-2515

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Hierarchical Chiral Framework Based on a Rigid Adamantane Tripod on Au(111)2007

    • Author(s)
      Satoshi, Katano, Yousoo, Kim, Hiroaki, Matsubara, Toshikazu, Kitagawa, Maki, Kawai
    • Journal Title

      Journal of the American Chemical Society vol.129

      Pages: 2511-2511

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Hierarchical Chiral Framework Based on a Rigid Adamantane Tripod on Au (111)2007

    • Author(s)
      Satoshi Katano, Yousoo Kim, Hiroaki Matsubara, Toshikazu Kitagawa, Maki Kawai
    • Journal Title

      Journal of the American Chemical Society 129巻9号

      Pages: 2511-2515

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis of Disubstituted Homodiamantanes by Acylative Ring Expansion Using Benzovl Trifluoromethanesulfonate2006

    • Author(s)
      岡崎隆男、万代修作、北川敏一、竹内賢一
    • Journal Title

      Science and Tecchnology of Advanced Materials 7巻

      Pages: 531-535

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Synthesis of Disubstituted Homodiamantanes by Acylative Ring Expansion Using Benzoyl Trifluoromethanesulfon2006

    • Author(s)
      Takao, Okazaki, Shusaku, Mandai, Toshikazu, Kitagawa, Ken'ichi, Takeuchi
    • Journal Title

      Science and Tecchnology of Advanced Materials vol.7

      Pages: 531-531

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Synthesis of Disubstituted Homodiamantanes by Acylative Ring Expansion Using Benzoyl Trifluoromethanesulfonate2006

    • Author(s)
      Takao Okazaki, Shusaku Mandai, Toshikazu Kitagawa, Ken'ichi Takeuchi
    • Journal Title

      Science and Tecchnology of Advanced Materials 7巻6号

      Pages: 531-535

    • Related Report
      2006 Annual Research Report
  • [Presentation] かさ高い置換基をもつアダマンタン分子三脚の合成と金(111)面上への単分子膜の形成2008

    • Author(s)
      中西志茉、水野 綾、北川敏一
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Year and Date
      2008-03-29
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
  • [Presentation] Synthesis of an Adamantane Tripod with Bulky Substituents and Preparation of Its Monolayer on Au(111)2008

    • Author(s)
      Shima, Nakanishi, Aya, Mizuno, Toshikazu, Kitagawa
    • Organizer
      88th Spring Meeting of the Chemical Society of Japan
    • Place of Presentation
      Rikkyo University
    • Year and Date
      2008-03-29
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 三脚形トリチオール-トリプチセン連結体の合成と金(111)面上における自己組織化単分子膜の形成2008

    • Author(s)
      宮崎友貴、平井克幸、北川敏一
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Year and Date
      2008-03-26
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] オリゴ(p-フェニレンエチニレン)をリンカーとする三脚形トリチオール-フェロセン連結体の合成と金(111)面上における単分子膜の電気化学的性質2008

    • Author(s)
      長谷隆啓、早川幾麻、北川敏一
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Year and Date
      2008-03-26
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of a Dyad Consisting of a Tripod-shaped Trithiol and Triptycene, and Preparation of Its Self-Assembled Monolayer on Au(111)2008

    • Author(s)
      Tomotaka, Miyazaki, Katsuyuki, Hirai, Toshikazu, Kitagawa
    • Organizer
      88th Spring Meeting of the Chemical Society of Japan
    • Place of Presentation
      Rikkyo University
    • Year and Date
      2008-03-26
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis of a Dyad Consisting of a Tripod-shaped Trithiol and Ferrocene Linked with an Oligo(p-phenyleneethynylene)Bridge and the Electrochemical Property of Its Monolayer on Au(111)2008

    • Author(s)
      Takahiro, Hase, Ikuma, Hayakawa, Toshikazu, Kitagawa
    • Organizer
      88th Spring Meeting of the Chemical Society of Japan
    • Place of Presentation
      Rikkyo University
    • Year and Date
      2008-03-26
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 三脚形トリチオールートリプチセン連結体の合成と金(111)面上における自己組織化単分子膜の形成2008

    • Author(s)
      宮崎 友貴、平井 克幸、北川 敏一
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Year and Date
      2008-03-26
    • Related Report
      2007 Annual Research Report
  • [Presentation] オリゴ(p-フェニレンエチニレン)をリンカーとする三脚形トリチオールーフェロセン連結体の合成と金(111)面上における単分子膜の電気化学的性質2008

    • Author(s)
      長谷 隆啓、早川 幾麻、北川 敏一
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Year and Date
      2008-03-26
    • Related Report
      2007 Annual Research Report
  • [Presentation] Hierarchical Chiral Framework Based on a Rigid Adamantane Tripod on Au(111)2007

    • Author(s)
      片野 諭、金 有洙、北川敏一、川合真紀
    • Organizer
      15th International Colloquium on Scanning Probe Microscopy(ICSPM15)
    • Place of Presentation
      伊豆熱川
    • Year and Date
      2007-12-06
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Hierarchical Chiral Framework Based on a Rigid Adamantane Tripod on Au(111)2007

    • Author(s)
      Satoshi, Katano, Yousoo, Kim, Toshikazu, Kitagawa, Maki, Kawai
    • Organizer
      15th International Colloquium on Scanning Probe Microscopy(ICSPM15)
    • Place of Presentation
      Atagawa
    • Year and Date
      2007-12-06
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Hierarchical Chiral Framework Based on a Rigid Adamantane Tripod on Au(111)2007

    • Author(s)
      片野 諭、金 有洗、北川 敏一、川合 真紀
    • Organizer
      15th International Colloquium on Scanning Probe Microscopy(ICSPMI5)
    • Place of Presentation
      伊豆摯川
    • Year and Date
      2007-12-06
    • Related Report
      2007 Annual Research Report
  • [Presentation] Adamantane Tripod as an Anchor for Functional Molecules and Its Ordered Monolayer on Au(111)2007

    • Author(s)
      北川敏一
    • Organizer
      CREST Workshop on Molecular Nano-Electronic Devices, MNED
    • Place of Presentation
      京都市
    • Year and Date
      2007-11-19
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Adamantane Tripod as an Anchor for Functional Molecules and Its Ordered Monolayer on Au(111)2007

    • Author(s)
      Toshikazu, Kitagawa
    • Organizer
      CREST Workshop on Molecular Nano-Electronic Devices, MNED
    • Place of Presentation
      Kyoto
    • Year and Date
      2007-11-19
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Adamantane Tripod as an Anchor for Functional Molecules and Its Ordered Monolayer on Au(111)2007

    • Author(s)
      北川 敏一
    • Organizer
      bREST Workshop on Molecular Nano-Electronic Devices, MNED
    • Place of Presentation
      京都市
    • Year and Date
      2007-11-19
    • Related Report
      2007 Annual Research Report
  • [Presentation] 活性種孤立化のための自己組織化単分子膜の作製2007

    • Author(s)
      宮崎友貴、早川幾麻、秋江大輔、平井克幸、北川敏一
    • Organizer
      第38回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      三重大学
    • Year and Date
      2007-11-10
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
  • [Presentation] Preparation of Self-Assembled Monolayers for the Isolation of Reactive Molecules2007

    • Author(s)
      Tomotaka, Miyazaki, Ikuma, Hayakawa, Daisuke, Akie, Katsuyuki, Hirai, Toshikazu, Kitagawa
    • Organizer
      38th Annual Meeting of Union of Chemistry-Related Societies in Chubu Area
    • Place of Presentation
      Mie University
    • Year and Date
      2007-11-10
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 活性種孤立化のための自己組織化単分子膜の作製2007

    • Author(s)
      宮崎友貴、早川幾麻、秋江大輔、平井克幸、北川敏一
    • Organizer
      第57回有機反応化学討論会
    • Place of Presentation
      広島大学
    • Year and Date
      2007-09-30
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
  • [Presentation] Preparation of Self-Assembled Monolayers for the Isolation of Reactive Molecules2007

    • Author(s)
      Tomotaka, Miyazaki, Ikuma, Hayakawa, Daisuke, Akie, Katsuyuki, Hirai, Toshikazu Kitagawa
    • Organizer
      57th Conference on Reaction Chemistry
    • Place of Presentation
      Hiroshima University
    • Year and Date
      2007-09-30
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Monoalkylated Fullerene Cations2007

    • Author(s)
      北川敏一
    • Organizer
      12th International Symposium on Novel Aromatic Compounds, ISNA-12
    • Place of Presentation
      淡路夢舞台
    • Year and Date
      2007-07-24
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
  • [Presentation] Monoalkylated Fullerene Cations2007

    • Author(s)
      Toshikazu, Kitagawa
    • Organizer
      12th International Symposium on Novel Aromatic Compounds, ISNA-12
    • Place of Presentation
      Awaji Yumebutai
    • Year and Date
      2007-07-24
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Monoalkylated Fullerene Cations2007

    • Author(s)
      北川敏一
    • Organizer
      4th Heron Island Conference on Reactive Intermediates and Unusual Molecules
    • Place of Presentation
      Heron Island, Australia
    • Year and Date
      2007-07-14
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Monoalkylated Fullerene Cations2007

    • Author(s)
      北川 敏一
    • Organizer
      4th Heron Island Conference on Reactive Intermediates and Unusual Molecules
    • Place of Presentation
      Heron lsland,Australia
    • Year and Date
      2007-07-14
    • Related Report
      2007 Annual Research Report
  • [Presentation] 金(111)面上におけるアダマンタン分子三脚-フェロセン連結化合物の自己組織化単分子膜の作製と電気化学的特性2006

    • Author(s)
      北川敏一、松原寛明、井戸本祐一、小松紘一
    • Organizer
      第18回基礎有機化学連合討論会
    • Place of Presentation
      九州産業大学
    • Year and Date
      2006-10-07
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] A Dyad Consisting of Adamantane Tripod and Ferrocene : Preparation and Electrochemical Propertiy of Self-assembled Monolayer on Au(111)2006

    • Author(s)
      Toshikazu, Kitagawa, Hiroaki, Matsubara, Yuichi, Idomoto, Koichi, Komatsu
    • Organizer
      18th Conference on Fundamental Organic Chemistry
    • Place of Presentation
      Kyushu Sangyo University
    • Year and Date
      2006-10-07
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary

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Published: 2006-04-01   Modified: 2016-04-21  

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