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Electrochiroptics : Novel Molecular Response System

Research Project

Project/Area Number 13440184
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionHokkaido University

Principal Investigator

SUZUKI Takanori  Hokkaido University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (70202132)

Co-Investigator(Kenkyū-buntansha) TSUJI Takashi  Hokkaido University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (20029482)
Project Period (FY) 2001 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥15,000,000 (Direct Cost: ¥15,000,000)
Fiscal Year 2002: ¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 2001: ¥12,800,000 (Direct Cost: ¥12,800,000)
KeywordsMolecular Response System / Molecular Device / Electrochromism / Redox System / Circular Dichroism / Chirality / Electron Donor / Functionalized Dye / 酸化還元素 / 分子不斉 / ビナフチル / ヘリセン / テトラシアノキノジメタン
Research Abstract

This research project is intended to construct the novel molecular response systems that transduce the electrochemical input into two kinds of spectral outputs, they are UV-Vis and CD spectra. These materials are named as "electrochiroptical response systems", and considered as promising candidates for use as chiral redox memories. Compared with the extensively studied electrochromic materials giving the UV-Vis spectral change as a sole output, there have been only a few successful examples reported so far. Based on our previous results on the multi-stage redox systems endowed with high electrochemical bistability, we have designed several chiral electron donors that can be reversibly transformed into the stable dicationic species. They exhibited drastic changes in UV-Vis as well as CD spectra during the interconversion. The high amplitude in CD signals is one of the central points to be considered in the molecular design, and we have realized it by exciton coupling of two identical chromophores located at the proper positions in these molecules. We are now planning to fix these molecules on the metal surface by making SAM, so that these molecules can be used as molecular devices.

Report

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

    (26 results)

All Other

All Publications (26 results)

  • [Publications] T.Suzuki, H.Higuchi, M.Ohkita, T.Tsuji: "Dual-Mode Electrochromism Switched by Proton Transfer : Dynamic Redox Properties of Bis(diarylmethylenium)-Type Dyes"Chem.Commun.. 1574-1575 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] J.Nishida, T.Suzuki, M.Ohkita, T.Tsuji: "A Redox Switch Based on Dihydro[5]helicene : Drastic Chiroptical Response Induced by Reversible C-C Bond Making/Breaking upon Electron Transfer"Angew.Chem.Int.Ed.. Vol.40. 3251-3254 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T.Suzuki, T.Tsuji, T.Ohkubo, A.Okada, Y.Obana T.Fukushima, T.Miyashi, Y.Yamashita: "Preparation, Structure, and Amphoteric Redox Properties of p-Phenylenediamine-type Dyes Fused with a Chalcogenadiazole Unit"J.Org.Chem.. Vol.66. 8954-8960 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T.Suzuki, T.Ono, H.Kawai, T.Tsuji: "Low-temperature X-ray structural Analysis Propanedinitrile Derivatives Substituted with a Bis (4-dimethylaminophenyl)methyl Group"J.Chem.Soc., Perkin Trans.2. 1798-1801 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T.Suzuki, R.Yamamoto, H.Higuchi, M.Ohkita, T.Tsuji: "Electrochiroptical Response of a Hexaarylethane Derivatives with a Helical π-Skeleton : Drastic UV-Vis and CD Spectral Changes upon Electrolysis of 4^1,5^1-Dibromodispiro[xanthene-9,9^1(9^1H,10^1H)-phenanthrene-10^1,9^<11>-xanthene]"J.Chem.Soc., Perkin Trans.2. 1937-1942 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T.Suzuki, J.Nishida, E.Hirota, M.Ohkita, T.Tsuji: "Chiral Electron Donors and Acceptors : Novel "Electrochiroptical" Response"Synth.Met.. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T.Suzuki, H.Higuchi, T.Tsuji, J.Nishida, Y.Yamashita, T.Miyashi: "Chemistry of Nanomolecular Systems : Toward the Realization of Molecular Device. Chapter 1 Dynamic Redox Systems : Toward the Realization of Unimolecular Memory"T.Nakamura, T.Matsumoto, H.Tada, K.Sugiura (Springer). 113 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T. Suzuki, H. Higuchi, M. Ohkita, T. Tsuji: "Dual-mode Electrochromism Switched by Proton-transfer : Dynamic Redox Properties of Bis(diarylmethylenium)-type Dyes"Chem. Commun.. 1574-1575 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] J. Nishida, T. Suzuki, M. Ohkita, T. Tsuji: "A Redox Switch Based on Dihydro[5]helicene : Drastic Chiroptical Response Induced by Reversible C-C Bond Making/Breaking upon Electron Transfer"Angew. Chem. Int. Ed.. 40. 3251-3254 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T. Suzuki, T. Tsuji, T. Ohkubo, A. Okada, Y. Obana, T. Fukushima, T. Miyashi, Y. Yamashita: "Prepartion, Structure, and Amphoteric Redox Properties of p-Phenylenediamine-type Dyes Fused with a Chalcogenadiazole Unit"J. Org. Chem.. 66. 8954-8960 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T. Suzuki, K. Ono, H. Kawai, T. Tsuji: "Low-temperature X-ray Structural Analysis of Propanedinitrile Derivatives Substituted with a Bis(4-dimethylaminophenyl)methyl Group : the Origin of Elongation of the Donor-acceptor Substituted C-C Bond"J. Chem. Soc., Perkin Trans.. 2. 1798-1801 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T. Suzuki, R. Yamamoto, H. Higuchi, E. Hirota, M. Ohkita, T. Tsuji: "Electrochiroptical Response of a Hexaarylethane Derivative with a Helical pai-Skeleton : Drastic UV-Vis and CD Spectral Changes upon Electrolysis of 4', 5'-Dibromodispiro[xanthene-9, 9'(9'H, 10H')-phenanthrene-10', 9'" -xanthene]"J. Chem. Soc., Perkin Trans.. 2. 1937-1942 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T. Suzuki, J. Nishida, E. Hirota, M. Ohkita, T. Tsuji: "Chiral Electron Donors and Acceptors : Novel 'Electrochiroptical' Response"Synth. Met.. in press.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T. Suzuki, H. Higuchi, T. Tsuji, J. Nishida, Y. Yamashita, T. Miyashi, T. Nakamura, T. Matsumoto, H. Tada, K. Sugiura, Eds.: "Chemistry of Nanomolecular Systems : Towards the Realization of Molecular Device. Chapter 1 Dynamic Redox Systems : Towards the Realization of Unimolecular Memory"Springer. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T.Suzuki, R.Yamamoto, H.Higuchi, M.Ohkita, T.Tsuji: "Electrochiroptical Response of a Hexaarylethane Derivatives with a Helical π-Skeleton : Drastic UV-Vis and CD Spectral Changes upon Electrolysis of 4',5'-Dibromodispire[xanthene-9,9(9'H,10'H)-phenanthrene-10',9"-xanthene]"J. Chem. Soc., Perkin Trans. 2. 1937-1942 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Suzuki, J.Nishida, E.Hirota, M.Ohkita, T.Tsuji: "Chiral Electron Donors and Acceptors : Novel "Electrochiroptical" Response"Synth. Met.. (印刷中). (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 西田純一, 鈴木孝紀, 辻 孝: "ヘキサフェニルエタン型化合物を基軸とした酸化還元型応答系の構築"有機合成化学協会誌. Vol.60. 40-51 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Ohkita, M.Kawano, T.Suzuki, T.Tsuji: "Supramolecular Graphyne : a C(sp)-H・・・N Hydrogen-bonded Unique Network Structure of 2,4,6-Triethynyl-1,3,5-triazine"Chem. Commun.. 3054-3055 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Tsuji, M.Okuyama, M.Ohkita, H.Kawai, T.Suzuki: "Functionalization and Kinetic Stabilization of the [4]Paracyclophane System and Aromaticity of Its Extremely Bent Benzene Ring"J. Am. Chem. Soc.. Vol.125. 951-961 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Suzuki, H.Higuchi, T.Tsuji, J.Nishida, Y.Yamashita, T.Miyashi: "Chemistry of Nanomolecular Systems : Toward the Realization of Molecular Device, Chaptar1 Dynamic Redox Systems : Toward The Realization of Unimolecular Memory"T.Nakamura, T.Matsumoto, H.Tada, K.Sugiura, (Springer). 113 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] T. Suzuki, H. Higuchi, M. Ohkita, T. Tsuji: "Dual-mode Electrochromism Switched by Proton Transfer : Dynamic Redox Properties of bis(diarylmerhylenium)-type dyes"Chem. Commun.. 1574-1575 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] J. Nishida, T. Suzuki, M. Ohkita, T. Tsuji: "A Redox Switch Based on Dihydro[5]halicene : Draotic Chiroptical Response Induced by Reversible C-C Bord Making/Breaking upon Electron Transfer"Angew. Chem. Int. Ed.. Vol 40. 3251-3254 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T. Suzuki, S. Miyamori, Y. Tsubota, T. Fukushima, T. Miyashi, Y. Yamashita, K. Imaeda, T. Ishida, T. Negami: "Single-Component Organic Conductors Based on Novel Radicals that Exhibit Electrochemical Amphotericity"J. Org. Chem.. Vol 66. 216-224 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T. Suzuki, M. Yamada, M. Ohkita, T. Tsuji: "Generation and Amphoteric Redox Properties of Novel Newtral Radicals with TTF-TCNQ Hybrid Structure"Heterocyles. Vol 54. 387-394 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T. Suzuki, K. Ono, H. Kawai, T. Tsuji: "Low-temperature X-ray structural Analysis of Propanedinitrile Derivatives Substituted with a bis(4-dimethylaminophenyl)methyl Group"J. Chem. Soc., Perkin Trans. 2. 1798-1801 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] T. Suzuki, T. Tsuji, T. Ohkubo, A. Okada, Y. Obana, T. Fukushima, T. Miyashi, Y. Yamashita: "Preparation, Structure, and Amphoteric Redox Properties of p-Phenylenediamine-Type Dyes Fused with a Chalcogenadiazole Unit"J. Org. Chem.. Vol 66. 8954-8960 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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