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Development of New Responsive Molecules Showing Piezo-pH Change and/or Piezochromism

Research Project

Project/Area Number 06650981
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionKyoto Institute of Technology

Principal Investigator

MIKI Sadao  Kyoto Institute of Technology Department of Chemistry and Materials Technology Assc.Prof., 工芸学部, 助教授 (30135537)

Project Period (FY) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1995: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1994: ¥1,100,000 (Direct Cost: ¥1,100,000)
Keywordsresponsiveness / piezochromism / acidity / photochromism / electrochromism
Research Abstract

Stimulus responsive molecules have been a subject of much recent interest because of their potentiality in wide range of material science. In this context, development of new responsive molecules of varieties with respect to the kinds of input-stimuli as well as properties responding to them. In this research project, several new responsive molecules have been synthesized, which showed responsivities such as piezo-pH,piezochromism, photo-pka, photochromism, as follows. 3,6-Dimitrothioxanthene-10,10-dioxide and 3-cyano-6-nitrothioxanthene-10,10-dioxide showed piezochromism upon pressing to give rise to color developing. The mechanism of the piezochromism has been studied in detail, that is, the conjugate base formed by the C (9) -H dissociation gave the color. This system changes the degree of the proton dissociation responding to pressure, and the phenomenon is closely relevant to piezo-pH change. This idea has been extended to light regulation of molecular acidity pka. It was intended … More to control the acidity of thioxanthene-10-10-dioxide by the light-driven structural change of a photoresponsive substituent introduced to the molecular skeleton. Thus, 3-methoxycarbonyl-6-trans-phenylazothioxanthene-10-10-dioxide and 3-methoxycarbonyl-6-trans-phenylazothioxanthene-10-10-dioxide were synthesized. The phenylazo group showed reversible trans/cis photo-isomerization, and the molecules of the trans form revealed much larger acidity than the cis-form. It has been intended to extend the light-driven property changes to the Redox potentials of a molecule. For this purpose, tri-butyl-polyacenequinones were synthesized. They undergo reversible photoisomerization between the corresponding valene isomer. The isomerizations are accompanied by large change in the pai-electronic structure, and as a result, are accompanied by large change in the Redox potential of the molecules. It was well known that the C60 possess an unique responsivity towards light. In order to materialize the property, it should be important to fix the molecule to solid materials. In this context, a new method for making C-C bond to C60 has been developed. Less

Report

(3 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • Research Products

    (17 results)

All Other

All Publications (17 results)

  • [Publications] H. Dodiuk: "Structure of Cyclodextrins and of Their Complexes. Chromatographic and NMR Study of 1,2,3-Tri-t-butyl-naphthalene and Its Complex with gamma-cyclodextrin." Tetrahedron. 50. 3619-3626 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] R. M. El-Shishtawy: "Synthesis and Photoreaction of 4,5,7-Tri-t-butylbenzo 〔c〕 thiophene : A Novel Benzo 〔c〕 thiophene Derivative and Its Dewar Isomer." Tetrahedron Lett.33. 3177-3180 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] S. Miki: "Introduction of Two Benzyl Groups to C60 by Using the Collman Reagent" Tetrahedron Lett.34(印刷中). (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] S. Miki: "Synthesis of 1,2,3-Tri-t-butyl-6,13-and 8,9,10-tri-t-butyl-5,14-pentasenequinones and Their Photochromic Behaviors : New Photochromic Molecules." Tetrahedron. 53. 4269-4276 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] S. Miki: "New Type of Photochromism in Thioxanthene-10-10-dioxide Derivatives Based on Their Photoresponsive Acidity Change." Chem. Lett.289-290 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Dodiuk, D.Syblska, S.Miki, Z.Yoshida: "Structure of Cyclodextrins and of Their Complexes. Chromatographic and NMR Study of 1,2,3-Tri-butyl-naphthalene and Its Complex with gamma-cyclodextrin." Tetrahedron. Vol.50, No, 11. 3619-3626 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] R.M.El-Shishtawy, K.Fukunishi, and S.Miki: "Synthesis and Photoreaction of 4,5,7-Tri-butylbenzo [c] thiophene : A Novel Benzo [c] thiophene Derivative and Its Dewar Isomer." Tetrahedron Lett.Vol.33. 3177-3180 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] S.Miki, M.Kitao, and K.Fukunishi: "Introduction of Two Benzyl Groups to C60 by Using the Collman Reagent" Tetrahedron Lett.Vol.34 (in press). (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] S.Miki, J.Ito, R.Noda, N.Nishijima, and K.Fukunishi: "Synthesis of 1,2,3-Tri-t-butyl-6,13-and 8,9,10-tri-t-butyl-5,14-pentasenequinones and Their Photochromic Behaviors : New Photochromic Molecules." Tetrahedron. Vol.53, No, 12. 4269-4276 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] S.Miki, Y.Ikeyama, and K.Fukunishi: "New Type of Photochromism in Thioxanthene-10-10-dioxide Derivatives Based on Their Photoresponsive Acidity Change." Chem.Lett.No, 4. 289-290 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] R.M.El-Shishtawy: "Synthesis and Photoreaction of 4, 5, 7-Tri-t-butylbenzo[c]thiophene:A Novel Benzd[c]thiophene Derivative and Its Dewar Isomer," Tetrahedron Lett.33. 3177-3180 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] S.Miki: "Introduction of Two Benzyl Groups to C60 by Using the Collman Reagent" Tetrahedron Lett.34 (in press). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] S.Miki: "Synthesis of 1, 2, 3-Tri-t-buty1-6, 13- and 8,9,10-tri-t-butyl-5, 14-pentasenequinones and Their Photochromic Behaviors:New Photochromic Molecules" Tetrahedron. 53. 4269-4276 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] S.Miki: "New Type of Photochromism in Thioxanthene-10-10-dioxide Derivatives Based on Their Photoresponsive Aciditr Change" Chem.Lett.289-290 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Toshiro.Nakayama: "Spectroscopic study of the formation and decay of intermediates for the novel photochemistry of sterically strained[6]-1,4-cyclophaneanthraquinone" Chem.Phys.Lett.220. 219-224 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Dodiuk: "Structure of Cyclodextrins and of Their Complexes.Chromatographic and NMR Study of 1,2,3-Tri-t-butylnaphthalene and Its Complex with gamma-cyclodextrin," Tetrahedron. 50. 3619-3626 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] R.M.El-Shishtawy: "Synthesis and Photoreaction of 4,5,7-Tri-t-butylbenzo[c]thiophene:A Novel Benzo[c]thiophene Derivative and Its Dewar Isomer," Tetrahedron Lett.(in press). (1995)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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