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Studies on elucidation of isomerization reaction of Schiff bases crystals and construction of novel proton flux. supramolecular systems

Research Project

Project/Area Number 14540498
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

KAWATO Toshio  Kyushu University, Faculty of Sciences, Professor, 大学院・理学研究院, 教授 (40038477)

Co-Investigator(Kenkyū-buntansha) KOYAMA Hiroyuki  Kyushu University, Faculty of Sciences, Professor, 大学院・理学研究院, 教授 (10038490)
AMIMOTO Kiichi  Kyushu University, Research and Development Center for Higher Education, Research Associate, 助手 (60294873)
Project Period (FY) 2002 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2004: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2003: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2002: ¥1,700,000 (Direct Cost: ¥1,700,000)
KeywordsPhotochromism / Photoisomerization / Organic crystals / Salicylideneamines / Schiff bases / Solid state reaction / Proton transfer / X-Ray crystallography / 包接化合物 / 光学異性体 / デオキシコール酸
Research Abstract

Experimantal finding of a cis-keto photoproduct derived from N-salicylideneaniline crystal.
Deuterium isotope kinetic effect in the solid state was observed by using thermal fading reaction of photo-coloured species derived from N-salicylideneaniline deuterohydroxyl derivative : thus, the existence of a cis-keto form in the photocoloured Schiff base crystals was suggested experimentally along with 6-methyl-substitution effect on the stability of the photoproduct.
Advantage of 2,6-dialkyl substituents of aniline for preparation of photochromic Schiff base crystals.
N-(3,5-Dihalosalicylidene)-2,6-dialkylaniline derivatives were prepared and their structure and photochromic properties were investigated. From the X-ray crystallography, it was revealed that steric repulsion between the azomethine hydrogen atom and the alkyl groups at the 2,6-positions of the aniline ring lead to a non-planar molecular structure, which was effective for the crystals to exhibit photochromism. The relationship between photochromicity and crystal packing of N-(3,5-dichlorosalicylidene)-2,6-dialkylanilines series was also discussed. The 2,6-dialkylaniline method was suggested to be applicable to the preparation of photochromic Schiff bases with various substituents in the salicylidene rings.
Photochromism of polymorphic 4,4'-methylenebis(N-salicylidene-2,6-diisopropylaniline) crystals.
4,4'-Methylenebis(N-salicylidene-2,6-dialkylaniline) derivatives were prepared and their structures were determined by ^1H NMR,IR,DSC and X-ray crystallographic analyses. The 2,6-diisopropylaniline derivative yielded definite polymorphic crystals : the space groups of the crystals were C2/c and P2_1/n, respectively. It was found that both polymorphs were similarly photochromic but the thermal stability of the photochrome was different due to the variance of the shape of molecule and cavity in each crystal.

Report

(4 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • 2002 Annual Research Report
  • Research Products

    (15 results)

All 2004 2003 2002 Other

All Journal Article (11 results) Publications (4 results)

  • [Journal Article] Photochromism of polymorphic 4,4' -methylenebis-(N-salicylidene-2,6-diisopropylaniline) crystals2004

    • Author(s)
      Masatsugu Taneda, Toshio Kawato et al.
    • Journal Title

      Organic and Biomolecular Chemistry 2

      Pages: 499-504

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Crystalline photochromism of N-salicylidene-2,6-dialkylanilines : advantage of 2,6-dialkyl substituents of aniline for preparation of photochromic Schiff base crystals2004

    • Author(s)
      H.Fukuda, K.Amimoto, H.Koyama, T.Kawat
    • Journal Title

      Organic and Biomolecular Chemistry 1

      Pages: 1578-1583

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Photochromism of polymorphic 4,4'-methylenebis-(N-salicylidene-2,6-diisopropylaniline) crystals2004

    • Author(s)
      M.Taneda, K.Amimoto, H.Koyama, T.Kawato
    • Journal Title

      Organic and Biomolecular Chemistry 2

      Pages: 499-504

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Photochromism of polymorphic 4,4'-mcthylcncbis-(N-salicylidenc-2,6-diisopropylanilinc crystals2004

    • Author(s)
      Masatsugu Tancda, Toshio Kawato et al.
    • Journal Title

      Organic and Biomolecular Chemistry 2

      Pages: 499-504

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Deuterium isotope effect on the solid-state thermal isomerization of photo-coloured cis-keto species of N-salicylideneaniline2003

    • Author(s)
      Kiichi Amimoto, Toshio Kawato et al.
    • Journal Title

      Chemical Communications

      Pages: 870-871

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] N-サリチリデンアニリン類結晶のフォトクロミズム2003

    • Author(s)
      網木貴一, 川東利男
    • Journal Title

      光化学 34・1

      Pages: 36-43

    • NAID

      80015916388

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Crystalline photochromism of N-salicylidene-2, 6-dialkylanilines : advantage of 2,6-dialkyl substituents of aniline for preparation of photochromic Schiff base crystals2003

    • Author(s)
      Hisatane Fukuda, Toshio Kawato et al.
    • Journal Title

      Organic and Biomolecular Chemistry 1

      Pages: 1578-1583

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Deuterium isotope effect on the solid-state thermal isomerization of photo-coloured cis-keto species of N-salicylideneaniline2003

    • Author(s)
      K.Amimoto, H.Kanatomi, A.Nagakari, H.Fukuda, H.Koyama, T.Kawato
    • Journal Title

      Chemical Communications

      Pages: 870-871

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Photochromism of N-Salicylideneanilines Crystals2003

    • Author(s)
      K.Amimoto, T.Kawato
    • Journal Title

      Photohemistry 34(1)

      Pages: 36-43

    • NAID

      80015916388

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Excited-state intramolecular proton transfer in photochromic jet-cooled N-salicylideneaniline2002

    • Author(s)
      Nobuo Otsubo, Toshio Kawato et al.
    • Journal Title

      Journal of Photochemistry and Photobiology A : Chemistry 154

      Pages: 33-39

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Excited-state intramolecular proton transfer in photochromic jet-cooled N-salicylideneaniline2002

    • Author(s)
      N.Otsubo, C.Okabe, H.Mori, K.Sakota, K.Amimoto, T.Kawato, H.Sekiya
    • Journal Title

      Journal of Photochemistry and Photobiology A : Chemistry 154

      Pages: 33-39

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] Kiichi Amimoto, Toshio Kawato 他: "Deuterium Isotope Effect on the Solid-State Thermal Isomerization of Photo-Colored cis-Keto Species of N-Salicylideneaniline"Chemical Communications. 870-871 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Hisatane Fukuda, Toshio Kawato 他: "Crystalline photochromism of N-salicylidene-2,6-dialkylanilines : advantage of 2,6-dialkyl substituents of aniline for preparation of photochromic Schiff base crystals"Organic & Biomolecular Chemistry. 1. 1578-1583 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Masatsugu Taneda, Toshio Kawato 他: "Photochromism of polymorphic 4,4'-methylenebis(N-salicylidene-2,6-diisopropylaniline) crystals"Organic & Biomolecular Chemistry. 2. 499-504 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Hiroshi Sekiya, Toshio Kawato他: "Excited-state intramolecular proton transfer in photochromic jet-cooled N-salicylideneaniline"J.Photochem.Photobiol., Chemistry. 154. 33-39 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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