• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

FUNCTIONALIZATION OF THE MOLECULE BY HYDROGEN BONDING AND PHOTOREACTION DYNAMICS

Research Project

Project/Area Number 10440166
Research Category

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

Allocation TypeSingle-year Grants
Section一般
Research Field Physical chemistry
Research InstitutionUNIVERSITY OF TSUKUBA

Principal Investigator

ARAI Tatsuo  DEPARTMENT OF CHEMISTRY, UNIVERSITY OF TSUKUBA PROFESSOR, 化学系, 教授 (50151139)

Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥13,500,000 (Direct Cost: ¥13,500,000)
Fiscal Year 2000: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 1999: ¥2,800,000 (Direct Cost: ¥2,800,000)
Fiscal Year 1998: ¥7,700,000 (Direct Cost: ¥7,700,000)
KeywordsHYDROGEN TRANSFER / TAUTOMERIZATION / EXCITED STATE / FLUORESCENCE / LASER PHOTOLYSIS / TRIPLET STATE / HYDROGEN BONDING / ISOMERIZATION / 断熱反応 / 励起三重項状態 / 水素原子移動
Research Abstract

The effect of inter- and intramolecular hydrogen bonding on the photochemical behaviors of aromatic compounds have been studied. Firstly, we have prepared a series of olefins with a pyrrole ring and a hetero aromatic ring such as pyridine or phenanthroline ring. In these olefins only the cis isomer forms intramolecular hydrogen bonding and showed intramolecular hydrogen atom transfer in the excited singlet state exhibiting fluorescence emission at considerably long wavelength region. Due to the hydrogen atom transfer only the trans→cis one-way photoisomerization has been observed. Secondly, we have revealed that intramolecular hydrogen bonding can control the efficiency and the mode of isomerization. Thus, 2'-hydroxychalcone, where both cis and trans isomers form 0-H : 0 intramolecular hydrogen bonding, exhibited intramolecular hydrogen atom transfer in the excited triplet state and finally resulted in one-way cis→trans isomerization around the C=C double bond. Thirdly, we have prepared a photochromic compound utilizing intramolecular hydrogen bonding exhibiting color change between reddish orange and greenish yellow by alternate irradiation with 366 nm and 546 nm light. Finally, we have prepared a series of donor-acceptor systems having 2-ureido-4 [1H]-pyrimidinone part which has very high association constant. In these systems photoinduced charge transfer interaction can take place even at very low concentration of the compounds by the aid of intramolecular hydrogen bonding.

Report

(4 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (38 results)

All Other

All Publications (38 results)

  • [Publications] Yanyan Yang: "Novel photochemical behavior of olefin with a pyrrole ring and a phenanthroline ring controlled by hydrogen bonding "Tetrahedron Letters. 39. 2617-2620 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tatsuo Arai: "Effect of formyl group on photoinduced hydrogen atom transfer and cis-trans isomerization of 2[2-(2-pyrrolyl)ethenyl] pyridine"Chemistry Letters. 1153-1154 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Shigeyuki Namiki: "Bis-N-nitroso-caged nitric oxides : Photochemistry and biological performance test by rat aorta vasorelaxation"Bioorganic & Medicinal Chemistry. 7. 1695-1702 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Yasuo Norikane: "Direct evidence of the hydrogen atom transfer in methyl salicylate in the triplet state"Chemistry Letters. 909-910 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tatsuo Arai: "Novel photochromic dye based on hydrogen bonding"Chemistry Letters. 965-966 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tatsuo Arai: "Photochemical cis-trans isomerization in the triplet state"Molecular and Supramolecular Photochemistry. 3. 131-167 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Morikatsu Yoshida: "Triplet sensitized laser flash photolysis of BNN3, caged nitric oxide"Chemistry Letters. 730-731 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Toshihide Suzuki: "Photoinduced intramolecular hydrogen atom transfer of N-salicylideneaniline in the triplet state "Chemistry Letters. 756-757 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Masashi Ikegami: "Photochromism of hydrogen bonded compounds"Molecular Crystals and Liquid Crystals. 345. 113-118 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Masashi Ikegami : "Laser flash photolysis study on hydrogen atom transfer of 2-(2-hydroxyphenyl)-benzoxazole and 2-(2-hydroxyphenyl) benzothiazole in the triplet excited state"Chemistry Letters. 996-997 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Yasuo Norikane: "Control of the photoisomerization mode of carbon-carbon double bond by intramolecular hydrogen bond ; one-way photoisomerization of 2'-hydroxy-chalcone induced by adiabatic intramolecular hydrogen atom transfer"Chemistry Letters. 1094-1095 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Toshihide Suzuki: "Novel Insight into the Photochromism and Thermochromism of Hydrogen Bonded Schiff Bases"Chemistry Letters. 124-125 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 新井達郎: "光異性化と水素結合:複雑系への展開を目ざして"光化学. 31. 100-107 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Yang and T.Arai: "Novel photochemical behavior of olefin with a pyrrole ring and a phenanthroline ring controlled by hydrogen bonding"Tetrahedron Letters. 39. 2617-2620 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Arai and Y.Hozumi: "Effect of formyl group on photoinduced hydrogen atom transfer and cis-trans isomerization of 2[2-(2-pyrrolyl)ethenyl] pyridine"Chemistry Letters. 1153-1154 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Namiki, F.Kaneda, M.Ikegami, T.Arai, K.Fujimori, S.Asada, H.Hama, Y.Kasuya, and K.Goto: "Bis-N-nitroso-caged nitric oxides : Photochemistry and biological performance test by rat aorta vasorelaxation"Bioorganic & Medicinal Chemistry. 7. 1695-1702 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Norikane and T.Arai: "Direct evidence of the hydrogen atom transfer in methyl salicylate in the triplet state"Chemistry letters. 909-910 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Arai and M.Ikegami: "Novel photochromic dye based on hydrogen bonding"Chemistry Letters. 965-966 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Arai: "Photochemical cis-trans isomerization in the triplet state"Molecular and Supramolecular Photochemistry Vol.3, Marcel Dekker, Inc.. 131-167 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Yoshida, M.Ikegami, S.Namiki, T.Arai, and K.Fujimori: "Triplet sensitized laser flash photolysis of BNN3, caged nitric oxide"Chemistry Letters. 730-731 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Suzuki, Y.Kaneko, and T.Arai: "Photoinduced intramolecular hydrogen atom transfer of N-salicylideneaniline in the triplet state"Chemistry Letters. 756-757 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Ikegami, T.Suzukii, Y.Kaneko, and T.Arai: "Photochromism of hydrogen bonded compounds"Molecular Crystals and liquid Crystals. 345. 113-118 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Ikegami and T.Arai: "Laser flash photolysis study on hydrogen atom transfer of 2-(2-hydroxyphenyl)-benzoxazole and 2-(2-hydroxyphenyl) benzothiazole in the triplet excited state"Chemistry Letters. 996-997 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Y.Norikane, H.Itoh, and T.Arai: "Control of the photoisomerization mode of carbon-carbon double bond by intramolecular hydrogen bond ; one-way photoisomerization of 2'-hydroxy-chalcone induced by adiabatic intramolecular hydrogen atom transfer"Chemistry Letters. 1094-1095 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Suzuki and T.Arai: "Novel Insight into the Photochromism and Thermochromism of Hydrogen Bonded Schiff Bases"Chemistry Letters. 124-125 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Morikatsu Yoshida: "Triplet sensitized laser flash photolysis of BNN3, caged nitric oxide"Chemistry Letters. 730-731 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Toshihide Suzuki: "Photoinduced intramolecular hydrogen atom transfer of N-salicylideneaniline in the triplet state"Chemistry Letters. 756-757 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Masashi Ikegami: "Photochromism of hydrogen bonded compounds"Molecular Crystals and Liquid Crystals. 345. 113-118 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Masashi Ikegami: "Laser flash photolysis study on hydrogen atom transfer of 2-(2-hydroxyphenyl)-benzoxazole and 2-(2-hydroxyphenyl) benzothiazole in the triplet excited state"Chemistry Letters. 996-997 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Yasuo Norikane: "Control of the photoisomerization mode of carbon-carbon double bond by intramolecular hydrogen bond ; one-way photoisomerization of 2'-hydroxy-chalcone induced by adiabatic intramolecular hydrogen atom transfer"Chemistry Letters. 1094-1095 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Toshihide Suzuki: "Novel Insight into the Photochromism and Thermochromism of Hydrogen Bonded Schiff Bases"Chemistry Letters. 124-125 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] 新井達郎: "光異性化と水素結合:複雑系への展開を目ざして"光化学. 31・2. 100-107 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Shigeyuki Namiki: "Bis-N-nitroso-caged nitric oxides:Photochemistry and biological performance test by rat aorta vasorelaxation."Bioorganic&Medicinal Chemistry. 7. 1695-1702 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Yasuo Norikane: "Direct evidence of the hydrogen atom transfer in methyl salicylate in the triplet state"Chemistry Letters. 909-910 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Tatsuo Arai: "Novel photochromic dye based on hydrogen bonding"Chemistry Letters. 965-966 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Tatsuo Arai: "Photochemical cis-trans isomerization in the triplet state"Molecular and Supramolecular Photochemistry. 3. 131-167 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Yanyan Yang: "Novel photochemical behavior of olefin with a pyrrole ring and a phenanthroline ring controlled by hydrogen bonding" Tetrahedron Letters. 39. 2617-2620 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 新井達郎: "Effect of formyl group on photoinduced hydrogen atom transfer and cis-trans isomerization of 2[2-(2-phyrrolyl)ethenyl]pyridine" Chemistry Letters. 1153 (1998)

    • Related Report
      1998 Annual Research Report

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi