Bulletin of the Korean Chemical Society

  • 제13권2호
  • /
  • Pages.140-145
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  • 1992
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  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Excited State Intramolecular Proton Transfer and Physical Properties of 7-Hydroxyquinoline

  • Kang Wee-Kyeong (Center for Molecular Science and Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Cho Sung-June (Center for Molecular Science and Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Lee Minyung (Spectroscopy Laboratory, Korea Research Institute of Standards and Science) ;
  • Kim Dong-Ho (Spectroscopy Laboratory, Korea Research Institute of Standards and Science) ;
  • Ryoo Ryong (Center for Molecular Science and Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Jung Kyung-Hoon (Center for Molecular Science and Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Jang Du-Jeon (Spectroscopy Laboratory, Korea Research Institute of Standards and Science)
  • 발행 : 1992.04.20
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초록

The excited state intramolecular proton transfer and physical properties of 7-hydroxyquinoline are studied in various solutions and heterogeneous systems by measuring steady state and time-resolved fluorescence, reflection and NMR spectra. Proton transfer is observed only in protic solvents owing to its requirement of hydrogen-bonded solvent bridge for proton relay transfer. The activation energies of the proton transfer are 2.3 and 5.4 kJ/mol in $CH_3OH$ and in $CH_3OD$, respectively. Dimers of normal molecules are stable in microcrystalline powder form and undergo an extremely fast concerted double proton transfer upon absorption of a photon, consequently forming dimers of tautomer molecules. In the supercage of zeolite NaY, its tautomeric form is stable in the ground state and does not show any proton transfer.

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참고문헌

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피인용 문헌

  1. Solvent-Controlled Excited State Behavior: 2-(2‘-Pyridyl)indoles in Alcohols vol.118, pp.14, 1996, https://doi.org/10.1021/ja952797d
  2. Excited‐State Prototropic Equilibrium Dynamics of 6‐Hydroxyquinoline Encapsulated in Microporous Catalytic Faujasite Zeolites vol.16, pp.42, 2010, https://doi.org/10.1002/chem.201000734
  3. Unraveling the Mechanism of the Photodeprotection Reaction of 8-Bromo- and 8-Chloro-7-hydroxyquinoline Caged Acetates vol.18, pp.22, 1992, https://doi.org/10.1002/chem.201200366
  4. Ground state spectroscopy of hydroxyquinolines: evidence for the formation of protonated species in water-rich dioxane–water mixtures vol.16, pp.1, 2014, https://doi.org/10.1039/c3cp52811a
  5. Non-typical fluorescence studies of excited and ground state proton and hydrogen transfer vol.5, pp.1, 2017, https://doi.org/10.1088/2050-6120/aa5e29
  6. 8-(Pyridin-2-yl)quinolin-7-ol as a Platform for Conjugated Proton Cranes: A DFT Structural Design vol.11, pp.10, 1992, https://doi.org/10.3390/mi11100901