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Synthesis and Photochemistry of Photochromic Compounds having Independent Functions

Research Project

Project/Area Number 02640334
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 物理化学一般
Research InstitutionYokohama National University

Principal Investigator

KURITA Yukio  YNU, Fac. of Eng. Professor, 工学部, 教授 (80114974)

Co-Investigator(Kenkyū-buntansha) YOKOYAMA Yasushi  YNU, Fac. of Eng. Assoc. Professor, 工学部, 助教授 (60134897)
Project Period (FY) 1990 – 1991
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1991: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1990: ¥1,700,000 (Direct Cost: ¥1,700,000)
KeywordsPhotochromism / Photoisomerization / Non-destructive read-out / Photomemory / Fulgide / Photochromic compound / 光異性化 / フリギド / チオインジゴ
Research Abstract

Fulgide is one of the most promising candidate to be applied to the erasable-and-rewritable photomemory. We have synthesized several fulgides and studied the relation between the molecular structure including the reaction media and the photochromic properties and obtained highly efficient photochromic fulgides with the large coloring as well as bleaching quantum yields. Recently we have tried to lengthen the absorption maximum of the colored form of fulgides and to develop the nondestructive read-out method, which is the most difficult problem to be solved in order to materialize the photochromic optical memory.
Synthesis of fulgide E ; (E) -3- [2- (5-dimethylamino-1, 2-dimethylindol-3-yl) ethylidene] -4-isopropylidene-3, 4-dihydrofuran-2, 5-dione ; was performed by Stobbe condensation of the corresponding substituted indole with diethyl isopropylidenesuccinate followed by hydrolysis and intramolecular acid anhydride formation processes. It has two distinctive characteristics : (i) the colored form (C) has the longest absorption maximum wavelength ever known as that of fulgid : (ii) the bleaching quantum yield of C is negligibly small. By adding strong acids such as trichloroacetic acid to a toluene solution, the protonation occured on the nitroge atom of the dimethylamino group to give EH or CH form. The latter recovered the photochromic nature to return to the bleached form EH. Because an equilibrium of rapid proton exchange exists between C, CH, E, and EH, the C and CH mixture entirely bleached to produce an E ad EH mixture. Similar reaction was observed in polymer films containing the fulgide and the acid. We suggest that the fulgide and trichloroacetic acid combination provides a model of a simple and efficient re-writable optical memory possessing non-destructive read-out ability. Namely, 554 nm light could be used for writing (or erasing), 403 nm light for erasing, and 780 nm light for non-destructive read-out.

Report

(3 results)
  • 1991 Annual Research Report   Final Research Report Summary
  • 1990 Annual Research Report
  • Research Products

    (24 results)

All Other

All Publications (24 results)

  • [Publications] 横山 泰: "A Nonーdestructic Readout Method of Photochromic Optical Memory Utilizing AcidーBase Equilibrium." 14th IUPAC Symposium on Photochemistry,1992 July Leuven. (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] 横山 泰: "Photochromism of Protonated 5ーdimethylaminoindolylfulgide:A Model of Nonーdestructive Readout for Photon Mode Optical Memory." J.Chem.Soc.,Chem.Commun.1722-1724 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] 横山 泰: "Synthesis and Photochromic Behavior of 5ーSubstituted Indolylfulgides" Chem.Lett.1125-1128 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] 横山 泰: "フルギド系フォトクロミック化成物の合成と光反応" 有機合成化学. 49. 364-372 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] 栗田 雄喜生: "Photochemistry and Photophysics of Photochromic Furylfulgides Having Bulky Alkyl Groups" 13th IUPAC Symposium on Photochemistry,1990,July Warwich. 154 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] 栗田 進: "Picosecond Flash Photolysis of a Photochromic Furylfulgide" Chem.Phys.Lett.171. 553-557 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Susumu Kurita, Akihide Kashiwagi, Yukio Kurita, Hiroshi Miyasaka, and Noboru Mataga: "Picosecond Flash Photolysis of a Photochromic Furylfulgide." Chem. Phys. Lett.171. 553-557 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Yasushi Yokoyama, Tatsuo Tanaka, Takeshi Yamane, and Yukio Kurita: "Synthesis and Photochromic Behavior of 5-Substituted Indolylfulgides" Chem. Lett.1125-1128 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Y. Yokoyama, T. Yamane, Y. Kurita: "Photochromism of Protonated 5-dimethylaminoindolylgide : A Model of Non-destructive Read-out for Photon Mode Optical Memory." J. Chem. Soc., Chem. Commun.1722-1724 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Yasushi Yokoyama and Yukio Kurita: "Synthesis and Photoreaction of Photochromic Fulgides." J. Synthetic Organic Chemistry. 49. 364-372 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Yukio Kurita, Susumu Kurita, Yasushi Yokoyama, Hiroshi Miyasaka, and Noboru Mataga: "Photochemistry and Photophysics of Photochromic Furylfulgides Having Bulky Alkyl Groups." 13th IUPAC Symposium on Photochemistry, Warwick. 154 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Y. Yokoyama, T. Yamane, and Y. Kurita: "A Non-destructive Read-out Method of Photochromic Optical Memory Utilizing Acid-Base Equilibrium." 14th IUPAC Symposium on Photochemistry, Leuven. (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] 横山 泰: "A nonーdestructive readout method of photochromic optical memory utilizing acidーbase eqilibrium" 14th IUPAC Symposium on Photochemistry 1992 July Leuven. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] 横山 泰: "Photochromism of protonated 5ーdimethylaminoindolylfulgide: A model of a nonーdestructive readout for a photon mode optical memory" J.Chem.Soc.,Chem.Commun.1722-1724 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 横山 泰: "Synthesis and photochromic behavior of 5ーsubstituted indolylfulgides" Chem.Lett.1125-1128 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 横山 泰: "フルギド系フォトクロミック化合物の合成と光反応" 有機合成化学. 49. 364-372 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 栗田 雄喜生: "Photochemistry and photophysics of photochromic furylfulgides having bulky alkyl groups" 13th IUPAC Symposium on Photochemistry 1990,July Warwick. 154 (1990)

    • Related Report
      1991 Annual Research Report
  • [Publications] 栗田 進: "Picosecond flash photolysis of a photochromic furylfulgide" Chem.Phys.Lett.171. 553-557 (1990)

    • Related Report
      1991 Annual Research Report
  • [Publications] 横山 泰: "Synthesis and photochromic behavior of 5ーsubstituted indolylfulgides" Chem.Lett.

    • Related Report
      1990 Annual Research Report
  • [Publications] 横山 泰: "フルギド系フォトクロミック化合物の合成と光反応" 有機合成化学. 49. (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] 栗田 進: "Picosecond flash photolysis of a photochromic furyfulgide" Chem.Phys.Lett.171. 553-557 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] 栗田 雄喜生: "Photochemicstry and photophysics of photochromic furylfulgides having bulky alkyl groups" 13th IUPAC Symposium on Phytochimistry. 154 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] 横山 泰: "Photochromism of a furylfulgide,2ー[1ー(2,5ーdimethylー3ーfuryl)ethylidene]ー3ーisopropylidenesuccinic anhydride in solvents" Bull.Chem.Soc.Jpn.63. 1607-1610 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] 横山 泰: "Steric effect of alkylidene groups of furylfulgides on the photochromic behavior" Chem.Lett.263-264 (1990)

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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