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1990 Fiscal Year Final Research Report Summary

Synthesis of Thermally Irreversible Photochromic Compounds and Their Application for Optical Data Storage Media

Research Project

Project/Area Number 01470098
Research Category

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

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionInstitute of Advanced Material Study, Kyushu Univ.

Principal Investigator

IRIE Masahiro  Institute of Advanced Materials Study, Kyushu Univ. Professor, 機能物質科学研究所, 教授 (30001986)

Project Period (FY) 1989 – 1990
KeywordsOptical Data Storage Media / Photochromic Reaction / Diaryethenes
Research Abstract

Photochromic compounds are characterized by exhibiting two different chemical forms. A reversible transformation from one to the other is induced by irradiation with light of an appropriate wavelength. The instant image forming property without processing has led to the consideration of their use in rewritable direct read after systems. The requirements for the reversible optical data storage media are followings. (1) Archival storage capability. (2) Low fatigue (can be cycled many times without any significant loss of performance). (3) Sensitivity at diode laser wavelength. (4) Non-destructive read out capability. The present study aimed at development of photohromic compounds which fulfill the above requirements. This was carried out by chemical modification of diarylethenes with heterocyclic rings.
In order to gain access to compounds which have sensitivity at longer wavelengths, symmetric diarylethenes with various heterocyclic rings, such as benzothiophene, selenophene, or indole r … More ing, were synthesized. Although diindolylmaleic anhydride shifted the absorption maximum of the closed-ring form to 620 nm, the closed-form was thermally unstable. In an attempt to get thermally stable compounds having the absorption bands at longer wavelengths, unsymmetrically substituted non-symmetric diarylethenes were synthesized. Non-symmetric maleic anhydride with indole ring on one end a thiophene ring on the other end became thermally stable and the absorption maximum of the closed-ring form was observed at 595 nm. The absorption maximum was further shifted to 680 nm by introducing a methoxy group at 5 position of the indole ring and a cyano group at 5 position of the thiophene ring. The non-symmetric compounds showed fatigue resistant property. The intensity of the closed-ring form of non-symmetric maleic anhydride with an indole ring on one end and a benzothiophene ring on the other end remained almost constant even after 1.1 x 10^4 ring-closure/ring-opening cycles. The next problem to be solved is to design compounds which have non-destructive read out capability. Less

  • Research Products

    (28 results)

All Other

All Publications (28 results)

  • [Publications] Y.Yoshioka,T.Tanaka M.Sawada,M.lrie: "Molowlar and Crystal structures of Eーand 2ーIsomers of 2.5ーDimethylー3ーfurylethylidene(isopropylidene)ーsucanic Anhydride" Chem.Let.19-22 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Irie: "Advances in Photo chromic Materials for Optiral Data storage Media" Jpn.J.Appl.Plwp. 28ー3. 215-219 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 入江 正浩: "有機フォトクロミック材料" PETROTECH. 12. 359-364 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 入江 正浩: "光機能高分子の研究開発動向" 機能材料. 9ー5. 5-10 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Kawauchi,H.Yoshida N.Yamashita,M.Ohira S.Saeda,M.Irie: "A New Photo chromic Spiro(3Hー1.4ーoxazine)" Bull Chem,Soc.,Jpn. 63. 267-268 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Uchida,Y.Nakayama M.Irie: "Thermally lrreversible Photo chromic Shstems.Reversible photocyclization of 1.2ーBis(benzo(6)thiophene ー3ーyl)ーethene Derivatives" Bull.Chem.Soc.,Jpn. 63. 1311-1315 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakayama,K.Hayashi,M.Irie: "Thermally Irreversible Photo chromic Systems.Revresible Photocyclization of 1.2ーDiselenenylethene and 1.2ーDiindolylー ethene Derivatives" J.Oig Chem.55. 2592-2596 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 中山 泰秀,入江 正浩: "熱安定性フォトクロミック化合物" 染料と薬品. 35. 298-311 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakayama,K.Hayashi,M.Irie: "Thermally lrrerer sible Photo chromic Systems.Photo reaction of diarylethene Derivatives with lmida20(1,2ーalpyridine Rings" Bull,chem.Soc.,Jpn. 64. 202-207 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nakayama,K.Hayashi,H.Irie: "Thermally lrrerersible Photo chromic Systems.Reversible Photo cyclization of NonーSummetric Dialylethene Derivatives" Bull.Chem.Soc.,Jpn. 64. 789-795 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 入江 正浩: "光メモリ機能をもつ超分子の設計" 化学工業. 42. 311-316 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Irie: "American Chemical Soaety" Polymers in Information Storage Technology. T105-116 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 入江 正浩: "クロミック材料と応用" シ-エムシ-,東京, T3-16 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Irie: "Photo responsive Materials" Material Research Soc.,Pittsburgh, T177-186 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y. Yoshioka, T. Tanaka, M. Sawada, M. Irie: ""Molecular and Crystal Structures of E- and Z-Isomers of 2, 5-Dimethyl-3-furylethylidene (isopropylidene)- succinic Anhydride" Chem. Lett.19-22 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Irie: "Advances in Photochromic Materials for Optical Data Storage Media" Jpn. J. Appl. Phys.28-3. 215-219 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Irie: "Organic Photochromic Materials" Petrotech. 12. 359-364 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Irie: "Current Research trend of Photoactive Polymers" Function & Materials. 9-5. 5-10 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S. Kawauchi, H. Yoshida, N. Yamashita, M. Ohira, M. Irie: "A New Photochronic Spiro (3H-1, 4-oxadine)" Bull. Chem. Soc. Jpn. 63. 267-268 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Uchida, Y. Nakayama, M. Irie: "Thermally Irreversible Photochromic Systems. Reversible Photocyclization of 1, 2-Bis (benzo (b)-thiophene-3-yl) ethene Derivatives" Bull. Chem. Soc. Jpn. 63. 1311-1315 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakayama, K. Hayashi, M. Irie: "Thermally Irreversible Photochromic Systems. Reversible Photocyclization of 1, 2-Diselenenylethene and 1, 2-diindolylethene Derivatives" J. Org. Chem.55. 2592-2596 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakayama, M. Irie: "Thermally Irreversible Photochromic Compounds" Dyestuffs & Chemicals. 35. 298-311 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakayama, K. Hayashi, M. Irie: "Thermally Irreversible Photochromic Systems. Photoreaction of Diarylethene Derivatives with Imidazo (1, 2-a) pyridine Rings" Bull. Chem. Soc. Jpn. 64. 202-207 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Nakayama, K. Hayashi, M. Irie: "Thermally Irreversible Photochromic Systems. Reversible Photocyclization of Non-symmetric Diarylethene Derivatives" Bull. Chem. Soc. Jpn. 64. 789-795 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Irie: "Molecular Design of Supramoleculer for Optical Memory Media" Chemical Industry. 42. 311-316 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Irie: "Thermally Irreversible Photochromic Compounds" Chromic Materials and Applications CMC. 3-16 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Irie: "Molecular Design for Thermally Irreversible Photochromic Compounds" Photoresponsive Materials, MRS. 177-186 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Irie: "Thermally Irreversible Photochromic Materials for Erasable Optical Data Storage Media" Polymers in Information Storage Technology, ACS. 105-116 (1989)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1993-08-12  

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