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A mechanistic study of a novel chemiluminescent reaction of arylhalides with LiTMP

Research Project

Project/Area Number 17550043
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

TUKADA Hideyuki  Yokohama City University, Internaticnal Graduate School of Artsand Sciences, Associate Professor, 大学院国際総合科学研究科, 准教授 (40171970)

Project Period (FY) 2005 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2006: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2005: ¥2,800,000 (Direct Cost: ¥2,800,000)
Keywordschemiluminescence / luminescence / lithium reagent / organic chemistry / mechanism
Research Abstract

We found a new chemiluminescent reaction, an arylhalide with lithium 2,2,6,6-tetramethylpiperidide (LiTMP) in tetrahydrofuran (THF). Owing to increasing importance of the luminescent process, mechanism of our chemiluminescent reaction was investigated.
The luminescence spectrum had an emission maximum at 610 nm. The spectrum was measured by use of optical fibers and a CCD detector. After aqueous work-up and subsequent column chromatograpy, we obtained a TMP substituted product and tetramethoxyanthracene. Fluorescent spectra of these products showed that these species did not correspond to that showing an emission maximum at 610nm. The chemiluminescence is not observed when the solvent was replaced with n-hexane, diphenyl ether, and diethyl ether. The reaction in THF proceeds via benzyne and benzyne-adduct with the enolate derived from THF, and finally gives anthracene derivative. Thus these potentially high-energy molecules are candidates for luminescent molecules.

Report

(3 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • Research Products

    (9 results)

All 2007 2005

All Journal Article (9 results)

  • [Journal Article] Conformational aspects of a benzyl ether dendron, methyl 1,3-bis(1,3-dimethoxybenzyloxy)benzoate : X-ray and density functional theory (DFT) studies2007

    • Author(s)
      Hideyuki Tukada, Katsura Mochizuki
    • Journal Title

      J. Molecular Structure (In press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Supramolecular structure of hydrogen bonded complexes between non-planar diphenols (bisphenol A and phenolphthalein) and triphenylphosphine oxide2007

    • Author(s)
      Hideyuki Tukada, Katsura Mochizuki
    • Journal Title

      J. Molecular Structure (In press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Conformational aspects of a benzyl ether dendron, methyl 1,3-bis(1,3-dimethoxybenzyloxy)benzoate : X-ray and density functional theory (DFT) studies2007

    • Author(s)
      Hideyuki Tukada, Katsura Mochizuki
    • Journal Title

      J.Molecular Structure (In press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Supramolecular structure of hydrogen bonded complexes between non-planar diphenols (bisphenol A and phenolphthalein) and triphenylphosphine oxide2007

    • Author(s)
      Hideyuki Tukada, Katsura Mochizuki
    • Journal Title

      J.Molecular Structure (In press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Conformational aspects of a benzyl ether dendron, methyl1,3-bis(1,3-dimethoxybenzyloxy)benzoate : X-ray and density functional theory(DFT)studies2007

    • Author(s)
      Hideyuki Tukada, katsura Mochizuki
    • Journal Title

      J. Molecular Structure (In press)

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Supramolecular structure of hydrogen bonded complexes between non-planar diphenols (bisphenol A and phenolphthalein) and triphenylphosphine oxide2007

    • Author(s)
      Hideyuki Tukada, katsura Mochizuki
    • Journal Title

      J. Molecular Structure (In press)

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Negative photochromism of a spiropyran in a Langmuir-Brodgett film.2005

    • Author(s)
      Y.Yokoyama, W.Hara, T.Inoue, T.Ubukata, M.Sakomura, H.Tukada
    • Journal Title

      Chemistry Letters 34

      Pages: 1622-1623

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] Hetero-atom stabilization of zwitterionic non-Kekule molecules : A DFT study on energy gaps between zwitterionic singlet and biradical triplet states.2005

    • Author(s)
      H.Tukada, P.R.Bangal, N.Tamai, Y.Yokoyama
    • Journal Title

      J. Molecular Structure (THEOCHEM) 724

      Pages: 215-219

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Hetero-atom stabilization of zwitterionic non-Kekule molecules : A DFT study on energy gaps between zwitterionic singlet and biradical triplet states.2005

    • Author(s)
      H.Tukada, P.R.Bangal, N.Tamai, Y.Yokoyama
    • Journal Title

      J.Molecular Structure (THEOCHEM) 724

      Pages: 215-219

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report

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Published: 2005-04-01   Modified: 2016-04-21  

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