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Construction of Enantioselective Photochromic System Controlled by Chirality of the Reaction-Field

Research Project

Project/Area Number 14540503
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionTokyo Kasei Gakuin University

Principal Investigator

YOKOYAMA Yayoi  Tokyo Kaseigakuin University, Faculty of Home Ecinimics, Associate Professor, 家政学部, 助教授 (70142263)

Project Period (FY) 2002 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2004: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 2003: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2002: ¥2,300,000 (Direct Cost: ¥2,300,000)
KeywordsDNA / Photochromism / Diarylethene / Spiropyran / Film / Intercalation / Amino Anthoracene / Quaternary Ammonium Ion Complex / 第四級アンモニウム塩 / 蛍光 / フォトクロミック反応 / 光環化反応 / フォトクトミズム / 複合材料 / 偏光吸収スペクトル / 吸光度 / 旋光度
Research Abstract

DNA- quaternary ammonium ion complex(DNA-QAIC) was obtained by the addition of dimethyldioctadecylammoniun salt to DNA, according to the procedures previously reported. We have clarified that DNA-QAIC can be the transparent matrices of photochromic reactions.
The stretched films of DNA-quaternary ammonium ion complex (DNA-QAIC) incorporating diarylethene exhibited large reversible change in optical rotation by its photochromic reactions.
Diarylethenes show similar conversion ratio to their colored form in solution, regardless of the presence or absence of the hydroxyl groups in their structure. The diarylethenes showed lower reactivity in DNA-QAIC film or in organic solvents like chloroform in the presence of DNA-QAIC, than in solution without DNA-QAIC. The diarylethene with hydroxyl groups at 2-positions of the benzothiophene rings, that is 1,2-bis(2-hydroxymethyl-3-benzothienyl)hexafluorocyclopentene, showed no coloration when it is dissolved in chloroform together with DNA-QAIC. It is … More because the conformation of the diarylethene was fixed to a non-cyclizable parallel conformation. It was suggested that the diarylethene molecules were partly intercalated between the DNA base pairs.
It is well-known that amioanthracene can intercalate between DNA base pairs. The diarylethene with an aminoanthracene intercalated at the anthracene moiety between the DNA base pairs in solution. As the result, fluorescence property changed to some extent, although the photochromic reaction was observed.
Although the photochromic reaction were not detected for the powder of spiropyran, the powder of DNA-QAIC incorporating spiropyran showed thermally reversible photochrimism. In this case, the spiropyran in the powder were considered to be intercalating into the DNA-QAIC, and DNA-QAIC can be the transparent matrices of photochromic reactions. The thermal decoloration reactions of spiropyrans in DNA-QAIC films was slower, and the absorbance at the photo-thermo-stationary state was smaller than those in polystyrene films. The structure and the motion of spiropyrans doped in the DNA-QAIC films were restricted, so that it was difficult to change to the corresponding merocyanine form. Less

Report

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

    (30 results)

All 2004 2003 Other

All Journal Article (23 results) Publications (7 results)

  • [Journal Article] Thermally Reversible Photochromism of Pyrazole Derivatives2004

    • Author(s)
      Yasushi Yokoyama
    • Journal Title

      Chemistry Letters 33(2)

      Pages: 106-107

    • NAID

      10012042319

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Diastereoselective Photochromism of Bisbenzothienylethenes with an Oxycarbonyl-Related Functional Group On the Side Chain2004

    • Author(s)
      Mahmut Kose
    • Journal Title

      The Journal of Organic Chemistry 69(24)

      Pages: 8403-8406

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Thermally Reversible Photochromism of Pyrazole Derivatives.2004

    • Author(s)
      Yasushi Yokoyama
    • Journal Title

      Chem.Lett. 33(2)

      Pages: 106-107

    • NAID

      10012042319

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Diastereoselective Photochromism of Bisbenzothienylethenes with an Oxycarbonyl-Related Functional Group On the Side Chain.2004

    • Author(s)
      Mahmut Kose
    • Journal Title

      J.Org.Chem. 69(24)

      Pages: 8403-8406

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Diastereoselective Photochromism of Bisbenzothienylethenes with an Oxycarbonyl-Related Functional Group On the Side Chain.2004

    • Author(s)
      Mahmut Kose
    • Journal Title

      The Journal of Organic Chemistry 69・24

      Pages: 8403-8406

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of Novel Thermally Reversible Photochromic Spiro[adamantine-2,7'(6'H)-benzothiophene]2003

    • Author(s)
      Yasushi Yokoyama
    • Journal Title

      Bulletin of the Chemical Society of Japan 46(2)

      Pages: 355-361

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthessis of Novel Thermally Irreversible Photochromic 1-Arvl-1,3-butadiene Derivatives.2003

    • Author(s)
      Sujen Man Shrestha
    • Journal Title

      Bulletin of the Chemical Society of Japan 76(2)

      Pages: 363-367

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Diastereoselective Photochromism of a Bisbenzothienylethene Governed by Steric as well as Electronic Interactions.2003

    • Author(s)
      Yasushi Yokoyama
    • Journal Title

      Journal of the American Chemical Society 125(24)

      Pages: 7194-7195

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Reversible Change in Optical Rotation by Photochromism of Diarylethenes in the Stretched DNA-Quaternary Ammonium Ion.2003

    • Author(s)
      Masako Saito
    • Journal Title

      Chemistry Letters 32(9)

      Pages: 806-807

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] DNAに取り込まれたジアリールエテン類のフォトクロミック反応挙動2003

    • Author(s)
      斉藤 雅子
    • Journal Title

      高分子論文集(Kobunshi Ronbunshu) 60(10)

      Pages: 581-589

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Preparation and Photochromic Properties of Powder and Films of DNA-Dodecyltrimethylammonium Ion Complex Containing Spiropyran Derivatives.2003

    • Author(s)
      Masako Saito
    • Journal Title

      Bulletin of the Chemical Society of Japan 76(12)

      Pages: 2423-2429

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Novel Thermally Reversible Photochromic Spiro[adamantine-2,7'(6'H)-benzothiophene].2003

    • Author(s)
      Yasushi Yokoyama
    • Journal Title

      Bull.Chem.Soc.Jpn. 76(2)

      Pages: 355-361

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthessis of Novel Thermally Irreversible Photochromic 1-Aryl-1,3-butadiene Derivatives.2003

    • Author(s)
      Sujen Man Shrestha
    • Journal Title

      Bull.Chem.Soc.Jpn. 76(2)

      Pages: 363-367

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Diastereoselective Photochromism of a Bisbenzothienylethene Governed by Steric as Well as Electronic Interactions.2003

    • Author(s)
      Yasushi Yokoyama
    • Journal Title

      J.Am.Chem.Soc. 125(24)

      Pages: 7194-7195

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Reversible Change in Optical Rotation by Photochromism of Diarylethenes in the Stretched DNA-Quaternary Ammonium Ion Complex Films.2003

    • Author(s)
      Masako Saito
    • Journal Title

      Chem.Lett. 32(9)

      Pages: 806-807

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] DNAに取り込まれたジアリールエテン類のフォトクロミック反応挙動2003

    • Author(s)
      斉藤雅子
    • Journal Title

      Kobunshi Ronbunshu 60(10)

      Pages: 581-589

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Preparation and Photochromic Properties of Powder and Films of DNA- Dodecyltrimethylammonium ion Complex Containing Spiropyran Derivatives.2003

    • Author(s)
      Masako Saito
    • Journal Title

      Bull.Chem.Soc.Jpn. 76(12)

      Pages: 2423-2429

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] 1,3-Bisarylbutadienes : Novel Thermally Irreversible Photochromic System

    • Author(s)
      Yasushi Yokoyama
    • Journal Title

      Mol.Cryst.Liq.Cryst. (印刷中)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Novel Thermally Reversible Photochromic Compounds : Dihydrobenzothiophene and Dihydronaphthalene

    • Author(s)
      Yasushi Yokoyama
    • Journal Title

      Mol.Cryst.Liq.Cryst. (印刷中)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] 1,3-Bisarylbutadienes : Novel Thermally Irreversible Photochromic System.

    • Author(s)
      Yasushi Yokoyama
    • Journal Title

      Mol.Cryst.Liq.Cryst. (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Novel Thermally Reversible Photochromic Compounds : Dihydrobenzothiophene and Dihydronaphthalene.

    • Author(s)
      Yasushi Yokoyama
    • Journal Title

      Mol.Cryst.Liq.Cryst. (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] 1,3-Bisarylbutadienes : Novel Thermally Irreversible Photochromic System.

    • Author(s)
      Yasushi Yokoyama
    • Journal Title

      Mol.Cryst.Liq.Cryst. (印刷中)

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Novel Thermally Reversible Photochromic Compounds : Dihydrobenzothiophene and Dihydronaphthalene.

    • Author(s)
      Yasushi Yokoyama
    • Journal Title

      Mol.Cryst.Liq.Cryst. (印刷中)

    • Related Report
      2004 Annual Research Report
  • [Publications] Yasushi Yokoyama: "Diastereoselective Photochromism of a Bisbenzothienylethene Governed by Steric as well as Electronic Interactions"Journal of the American Chemical Society. 125・24. 7194-7195 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Masako Saito: "Reversible Change in Optical Rotation by Photochromism of Diarvlethenes in the Stretched DNA-Quaternary Ammonium Ion"Chemistry Letters. 32・9. 806-807 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 斉藤 雅子: "DNAに取り込まれたジアリールエテン類のフォトクロミック反応挙動"高分子論文集(Kobunshi Ronbunshu). 60・10. 581-589 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Masako Saito: "Preparation and Photochromic Properties of Powder and Films of DNA-Dodecyltrimethylammonium Ion Complex Containing Spiropyran Derivatives"Bulletin of the Chemical Society of Japan. 76・12. 2423-2429 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yasushi Yokoyama: "Thermally Reversible Photochromism of Pyrazole Derivatives"Chemistry Letters. 33・2. 106-107 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yasushi Yokoyama: "Synthesis of Novel Thermally Reversible Photochromic Spiro [adamantine-2,7'(6'H)-benzothiophene]"Bulletin of the Chemical Society of Japan. 76(2). 355-361 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Sujen Man Shrestha: "Synthessis of Novel Thermally Irreversible Photochromic 1-Aryl-1,3-butadiene Derivatives"Bulletin of the Chemical Society of Japan. 76(2). 363-367 (2003)

    • Related Report
      2002 Annual Research Report

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

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