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Study on the catalytic role of hydrogen-bond in the phtoinduoed cis【tautomer】trans isomerization of napththol

Research Project

Project/Area Number 15350002
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Physical chemistry
Research InstitutionHIROSHIMA UNIVERSITY (2004)
Tohoku University (2003)

Principal Investigator

EBATA Takayuki  Hiroshima University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (70142924)

Co-Investigator(Kenkyū-buntansha) MIKAMI Naohiko  Tohoku University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (70004447)
FUJII Asuka  Tohoku University, Graduate School of Science, Associate Professor, 大学院・理学研究科, 助教授 (50218963)
Project Period (FY) 2003 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥15,300,000 (Direct Cost: ¥15,300,000)
Fiscal Year 2004: ¥3,900,000 (Direct Cost: ¥3,900,000)
Fiscal Year 2003: ¥11,400,000 (Direct Cost: ¥11,400,000)
Keywordsisomerization / catalysis / hydrogen-bond / double resonance / laser manipulation / supersonic jet / naphthol / コンフォメーション / シス体、トランス体 / 超音速分子線 / 紫外-赤外二重共鳴分光法 / シス-トランス異性化反応 / 水素結合クラスター / 二重共鳴分光 / 2-ナフトール
Research Abstract

There are two isomeric forms in naphthol, depending on the orientation of hydroxyl group with respect to the naphthalene ring, which are called cis and trans. The existence of the two rotational isomers was first proposed by Ito and coworkers by uses of laser spectroscopic technique combined with a supersonic jet. Later, Pratt and coworkers assigned them by analyzing rotationally resolved electronic spectrum of jet cooled naphthol. Since then, the possibility of the laser manipulation of cis【tautomer】trans isomerization has been discussed by several researchers. Up to now, however, it has not been realized yet. In this research, we aimed to manipulate the cis【tautomer】trans isomerization for electronically excited by use of UV-IR stepwise excitation in a supersonic jet. First, a specific isomer was selectively excited to the S_1 state with a tunable UV laser pulse. The molecule or cluster in S_1 is further excited to its X-H stretching vibration by the IR laser pulse, where X refers to … More the C,O or N atom. The energy put in to the X-H stretching vibration is immediately redistributed into other vibrartional modes by IVR, and part of them will flow into the iromerization coordinate. If the energy is large enough to overcome the isomerization barrier, the reaction will occur and the product emits fluorescence.
We investigated not only bare molecule but also the hydrogen-bonded clusters and found that the reaction does not occur for bare molecule within the examined energy region up to 3510 cm^<-1>. On the other hand, the reaction occurred at 2900 cm^<-1> for hydrogen-bonded clusters. Such a larger reduction indicates that H-bond acts as a catalyst for the reaction. Furthermore, we fond in the clusters the cis-trans isomerization occurs very efficiently at low IR frequency but the yield decrease rapidly with the energy due to the competition with the dissociation of H-bond within the same isomer. The isomerization occurred both 1- and 2-napthol H-bonded clusters and the barrier height seems to be similar between them. Parallel to the experiments, we performed DFT and time-dependent DFT calculation to obtain the isomerization barrier height and to investigate the effect of H-bond in S_0, S_1 and S_2 states. Thought the calculation predicted large increase of the barrier height in S_1, it failed the decrease of the height upon the H-bond formation. Further calcuation is in progress. Less

Report

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

    (23 results)

All 2004 2003 Other

All Journal Article (17 results) Publications (6 results)

  • [Journal Article] Picosecond IR-UV pump-probe spectroscopic study on the dynamics of vibrational relaxation of jet-cooled phenol I-IVR of the OH and CH stretching vibrations of bare phenol-.2004

    • Author(s)
      Y.Yamada et al.
    • Journal Title

      J.Chem.Phys. 120

      Pages: 7400-7409

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Picosecond IR-UV pump-probe spectroscopic study on the dynamics of vibrational relaxation of jet-cooled phenol II - IVR of the OR stretching vibration of hydrogen-bonded clusters2004

    • Author(s)
      M.Kayano et al.
    • Journal Title

      J.Chem.Phys. 120

      Pages: 7410-7417

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Infrared spectroscopic evidence for protonated water clusters forming nanoscale cages2004

    • Author(s)
      M.Miyazaki et al.
    • Journal Title

      Science 304

      Pages: 1034-1137

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] Picosecond IR-UV pump-probe spectroscopic study on the dynamics of vibrational relaxation of jet-cooled phenol I-IVR of the OH and CH stretching vibrations of bare phenol-.2004

    • Author(s)
      Y.Yamada, T.Ebata, M.Kayano, N.Mikami
    • Journal Title

      J.Chem.Phys. 120

      Pages: 7400-7409

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Picosecond IR-UV pump-probe spectroscopic study on the dynamics of vibrational relaxation of jet-cooled phenol II-IVR of the OH stretching vibration of hydrogen-bonded clusters2004

    • Author(s)
      M.Kayano, T.Ebata, Y.Yamada, N.Mikami
    • Journal Title

      J.Chem.Phys. 120

      Pages: 7410-7417

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Infrared spectroscopic evidence for protonated water clusters forming nanoscale cages.2004

    • Author(s)
      M.Miyazaki, A.Fujii, T.Ebata, N.Mikami
    • Journal Title

      Science 304

      Pages: 1134-1137

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Picosecond IR-UV pump-probes spectroscopic study on the dynamics of vibrational relaxation of jet-cooled phenol I -IVR of the OH and CH stretching vibrations of bare phenol-.2004

    • Author(s)
      Y.Yamada et al.
    • Journal Title

      J.Chem.Phys. 120

      Pages: 7400-7409

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Picosecond IR-UV pump-probe spectroscopic study on the dynamics of vibrational relaxation of jet-cooled phenol II -IVR of the OH stretching vibration of hydrogen-bonded clusters2004

    • Author(s)
      M.Kayano et al.
    • Journal Title

      J.Chem.Phys. 120

      Pages: 7410-7417

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Hydrogen transfer in excited pyrrole-ammonia clusters2004

    • Author(s)
      O.David et al.
    • Journal Title

      J.Chem.Phys. 120

      Pages: 10101-10110

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Real-time detection of doorway states in the intramolecular vibrational Energy redistribution of the OH/OD stretch vibration of phenol2004

    • Author(s)
      Y.Yamada et al.
    • Journal Title

      J.Chem.Phys. 121

      Pages: 10530-10534

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Infrared spectroscopy of size-selected benzene-water cluster cations [C_6H_6-(H_2O)_n]^+ (n=1-23):Hydrogen bond network evolution and microscopic hydrophobicity2004

    • Author(s)
      M.Miyazaki et al.
    • Journal Title

      J.Phys.Chem.A 108

      Pages: 10656-10660

    • Related Report
      2004 Annual Research Report
  • [Journal Article] NH stretching vibrations of jet-cooled aniline and its derivatives in the neutral and cationic states2003

    • Author(s)
      M.Honda et al.
    • Journal Title

      J.Phys.Chem.A 107

      Pages: 3678-3686

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Infrared spectroscopy of hydrated benzene cluster cations, [C_6H_6-(H_2O)_n]^+ Structural changes upon photoionization and proton transfer2003

    • Author(s)
      M.Miyazaki et al.
    • Journal Title

      Phys.Chem.Chem.Phys. 5

      Pages: 1137-1148

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] IR induced cis-trans isomerization of 2-naphthol -Catalytic role of hydrogen-bond in the photochemical isomerization2003

    • Author(s)
      T.Ebata et al.
    • Journal Title

      J.Chem.Phys. 119

      Pages: 2947-2950

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] NH stretching vibrations of jet-cooled aniline and its derivatives in the neutral and cationic states2003

    • Author(s)
      M.Honda, A.Fujii, E.Fujimaki, T.Ebata, N.Mikami
    • Journal Title

      J.Phys.Chem.A. 107

      Pages: 3678-3686

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Infrared spectroscopy of hydrated benzene cluster cations, [C_6H_6-(H_2O)_n]^+ : Structural changes upon photoionization and proton transfer2003

    • Author(s)
      M.Miyazaki, A.Fujii, T.Ebata, N.Mikami
    • Journal Title

      Phys.Chem.Chem.Phys. 5

      Pages: 1137-1148

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] IR induced cis-trans isomerization of 2-naphthol -Catalytic role of hydrogen-bond in the photochemical isomerization2003

    • Author(s)
      T.Ebata, K.Kouyama, N.Mikami
    • Journal Title

      J.Chem.Phys. 119

      Pages: 2947-2950

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] Masaji Honda: "NH stretching vibrations of jet-cooled aniline and its derivatives in the neutral and cationic states"J.Phys.Chem.A.. 107. 3678-3686 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Mitsuhiko Miyazaki: "Infrared spectroscopy of hydrated benzene cluster cations,[C_6H_6-(H_2O)_n]^+ : Structural changes upon photoionization and proton transfer"Phys.Chem.Chem.Phys.. 5. 1137-1148 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Takayuki Ebata: "IR induced cis-trans isomerization of 2-naphthol -Catalytic role of hydrogen-bond in the conformational isomerizaion-"J.Chem.Phys.. 119. 2947-2950 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Eman Abd El-Hakam Abou El-Nasr: "Substitution effects on the excited state intramolecular proton transfer of salicylic acid : An infrared spectroscopic study on the OH stretching vibrations of jet-cooled 5-methoxysalicylic acid"Chem.Phys.Lett.. 376. 788-793 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yuji Yamada: "Picosecond IR-UV pump-probe spectroscopic study on the dynamics of the vibrational relaxation of jet-cooled phenol I -IVR of the OH and CH stretching vibrations of bare phenol-"J.Chem.Phys. (印刷中).

    • Related Report
      2003 Annual Research Report
  • [Publications] Masakazu Kayano: "Picosecond IR-UV pump-probe spectroscopic study on the dynamics of the vibrational relaxation of jet-cooled phenol II -IVR of the OH stretching vibration of hydrogen-bonded clusters-"J.Chem.Phys.. (印刷中).

    • Related Report
      2003 Annual Research Report

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Published: 2003-04-01   Modified: 2016-04-21  

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