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Synthesis of Photoactive Dendrimers

Research Project

Project/Area Number 09450353
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionKYUSHU UNIVERSITY

Principal Investigator

IRIE Masahiro  Graduate School of Engineering, KYUSHU UNIVERSITY,Professor, 大学院・工学研究科, 教授 (30001986)

Co-Investigator(Kenkyū-buntansha) TAKESHITA Michinori  Graduate School of Engineering, KYUSHU UNIVERSITY,Assistant, 大学院・工学研究科, 助手 (40274534)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1998: ¥1,200,000 (Direct Cost: ¥1,200,000)
KeywordsDendrimr / Photochromism / Fluorescence Quenching / 自由体積 / デンドリュー / 蛍光 / デンドリマ-
Research Abstract

Dendrimers having a photochromic or a fluorescent chromophore in the core group were synthesized. The dendrimers were prepared by the convergent synthetic method developed by Frechet et al. Two equivalent of the bromo substituted dendric fragments were reacted with on equivalent 1,2-bis[2,4- dimethyl-5-(4'-hydroxyphenyl)thiophen-3-yl] perfluorocyclopentene or one equivalent 9,10- dihydroxymethylanthracene. The dendrimers were purified by flash chromatography and repetitive preparative TLC.
We introduced bulky dendric groups into the dithienylethene in an attemp to change the ratio of two conformers, parallel and anti-parallel, and to increase the cyclization quantum yield. However, the dendric groups (even the third generation) did not alter the ratio of the two conformers. This result indicates that the free volume of the core part is large enough for the rotaion of the aryl groups. Fluorescence quenching of the core anthracene by N,N-diethylaniline was examined. Fluorescence quenching constants were dramatically decreased with the increasing generation. The quenching mechanism was studied in detail.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (28 results)

All Other

All Publications (28 results)

  • [Publications] T.Tsujioka,M.Kume,M.Irie: "Photochromic Reactions of a Diarylethene Derivative in Polymer Matrices" J.Photochem.Photobio.A: Chem.104. 203-206 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Irie,T.Eriguchi,T.Takada,K.Uchida: "Photochromism of Diarylethenes Having Thiophene Oligomers as the Aryl Groups" Tetrahedron. 53. 12263-12271 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] J.Hellmann,M.Hamano,M.Irie,K.Ijiro,M.Shimomura,O.Karthaus.: "Aggregation of Dendrimers with a Photochromic Dithienylethene Core Group on the Mica Surface-Atomic Force Microscopic Imaging" Jpn.J.Appl.Phys.37. L816-L819 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Nakashima,M.Irie: "Synthesis of Polystyrene and Poly(alkyl methacrylate)s Having Photochromic Dithienylethene Pendant Groups" Polymer J.30. 985-989 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Takeshita,N.Kato,S.Kawauchi,T.Imase,J.Watanabe,M.Irie: "Photochromism of Dithienylethenes Included in Cyclodextrins" J.Org.Chem.63. 9306-9313 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Irie, K.Uchida: "Synthesis and Properties of Photochromic Diarylethenes with Heterocyclic Aryl Groups" Bull.Chem.Soc.Jpn.71. 985-996 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Irie: "Organic Photochromic and Thermochromic Compounds" Plenum Pub.New York, 13 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Irie: "Functionality of Molecular Systems 2" Springer,Tokyo, 6 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Tsujioka, M.Kume, M.Irie: "Photochromic Reactions of a Diarylethene Derivative in Polymer Matrices" J.Photochem.Photobio.A : Chem.Vol.104. 203-206 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Irie, T.Eriguchi, T.Takada, K.Uchida: "Photochromism of Diarylethenes Having Thiophene Oligomers as the Aryl Group" Tetrahedron. Vol.53. 12263-12271 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] J.Hellmann, M.Hamano, O.Karthaus, K.Ijiro, M.Shimomura, M.Irie: "Aggregation of Dendrimers with a Photchromic Dithienylethene Core Group on the Mica Surface-Atomic Force Microscopic Imaging" Jpn.J.Appl.Phys.Vol.37. L816-L819 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Nakashima, M.Irie: "Synthesis of Polystyrene and Poly (alkyl methacrylate) s Having Photochromic Dithienylethene Pendant Groups" Polymer J.Vol.30. 985-989 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Takeshita, N.Kato, S.Kawauchi, T.Imase, J.Watanabe, M.Irie: "Photochromism of Dithienylethenes Included in Cyclodextrins" J.Org.Chem.Vol.63. 9306-9313 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Irie, K.Uchida: "Synthesis and Properties of Photochromic Diarylethenes with Heterocyclic Aryl Groups" Bull.Chem.Soc.Jpn.Vol.71. 985-996 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] J.Hllmann,N.Hamano,O.Katrthaus.K.Ijiro,M.Shimomura,M.Irie: "Aggregation of Dendrimers with a Photochromic Dithienylethene Core Group on the Mica Surface-Atomic Force Microscopic Imaging" Jpn.J.Appl.Phys.37. L819-L819 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] H.Nakashima,M.Irie: "Synthesis of Polystyrene and Poly(alkyl methacrylate)s Having Photochromic Dithienylethene Pendant Groups" Polymer J.30. 9306-9313 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Takeshita,N.Kato,S.Kawauchi,T.Imase,J.Watanabe,M.Irie: "Photochromism of Dithienylethenes Included in Cyclodextrins" J.Org.Chem.63. 9306-9313 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Irie,K.Uchida: "Synthesis and Properties of Properties of Photochromic Diarylethenes with Heterocyclic Aryl Groups" Bull.Chem.Soc.Jpn.71. 985-989 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Takeshita,M.Irie: "Photoreversible Circular Dichroism Chenge of 1,2-Bis(1-benzothiophen-3-yl)- perfluorocycropentene Modified Cyclodextrin" Tetrahedron Lett.40. 1345-1348 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] K.Uchida,E.Tsuchida,Y.Aoi,S.Nakamura,M.Irie: "Subastitution Effect on the Coloration Quantum Yield of a Photochromic Bisbenzethienylethene" Chem.Lett. 63-64 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Irie: "Organic Photochromic and Thermochromic Compounds" Plenum Pub.New York, 13 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Irie: "Functionality of Molecular Systems 2" Springer,Tokyo, 6 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Takeshita,C.N.Choi,M.Irie: "Enhancement of the Photocyclization Quantum Yieldof 2,2'-Dimethyl-3,3'-(perfluorocyclopentene-1,2-diyl)bis(benzo[b]thiophene-6-sulfonate)by Inclusion in a Cyclodextrin Cavity" J.Chem,.Soc.Chem.Commun.2265-2266 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] T.Tsujioka,M.Kume,M.Irie: "Photochromic Reactions of a Diarylethene Derivative in Polymer Matrices" J.Potochem.Photobio.A:Chem.104. 203-206 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] H.Miyasaka,T.Nobuto,A,Itaya,N.Tamai,M.Irie: "Picosecond Laser Photolysis Studies on Photochromic Dithienylethenes in Solution and in Crystalline Phases" Chem.Phys.Lett.269. 281-285 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Y.Kaneuchi,T.Kawai,M.Hamaguchi K.Yoshino,M.Irie: "Optical Properties of Photochromic Dyes in the Amorphous State" Jpn.J.Appl.Phys.36. 3736-3739 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] T.Yamaguchi,K.Uchida,M.Irie: "Asymmetric Photocyclization of Diarylethene Derivatives" J.Am,Chem.Soc.119. 6066-6071 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Irie,T.Eriguchi,T.Takada,K.Uchida: "Photochromism of Diarylethenes Having Thiophene Oligomers as the Aryl Groups" Tetrahedron. 53. 12263-12271 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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