메뉴 건너뛰기




Volumn 4, Issue 4, 2005, Pages 367-375

Intramolecular and intermolecular hydrogen-bonding effects on photophysical properties of 2′-aminoacetophenone and its derivatives in solution

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; OXYGEN; SOLVENT;

EID: 17544384074     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b416284f     Document Type: Article
Times cited : (40)

References (51)
  • 1
    • 0020799484 scopus 로고
    • Picosecond laser photolysis studies of deactivation processes of excited hydrogen-bonding complexes. 3. Detection of the nonfluorescent charge-transfer state in the excited 1-aminopyrene-pyridine hydrogen-bonded pair and related systems
    • N. Ikeda H. Miyasaka T. Okada N. Mataga Picosecond laser photolysis studies of deactivation processes of excited hydrogen-bonding complexes. 3. Detection of the nonfluorescent charge-transfer state in the excited 1-aminopyrene-pyridine hydrogen-bonded pair and related systems J. Am. Chem. Soc. 1983 105 5206-5211.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 5206-5211
    • Ikeda, N.1    Miyasaka, H.2    Okada, T.3    Mataga, N.4
  • 2
    • 0000176452 scopus 로고
    • Deactivation of excited 2-naphthylamine due to hydrogen-bonding interaction with pyridines. Fluorescence and picosecond laser photolysis studies
    • N. Ikeda T. Okada N. Mataga Deactivation of excited 2-naphthylamine due to hydrogen-bonding interaction with pyridines. Fluorescence and picosecond laser photolysis studies Bull. Chem. Soc. Jpn. 1981 54 1025-1030.
    • (1981) Bull. Chem. Soc. Jpn. , vol.54 , pp. 1025-1030
    • Ikeda, N.1    Okada, T.2    Mataga, N.3
  • 4
    • 0034636525 scopus 로고    scopus 로고
    • Femtochemistry of hydrogen-bonded complexes after electronic excitation in liquid phase: The case of coumarin 102
    • E. T. J. Nibberling F. Tschirschwitz C. Chudoba T. Elsaesser Femtochemistry of hydrogen-bonded complexes after electronic excitation in liquid phase: the case of coumarin 102 J. Phys. Chem. A 2000 104 4236-4246.
    • (2000) J. Phys. Chem. A , vol.104 , pp. 4236-4246
    • Nibberling, E.T.J.1    Tschirschwitz, F.2    Chudoba, C.3    Elsaesser, T.4
  • 5
    • 0001513005 scopus 로고
    • Solution photophysics of 1- and 3-aminofluorenone: The role of inter- and intramolecular hydrogen-bonding in radiationless deactivation
    • R. S. Moog N. A. Burozski M. M. Desai W. R. Good C. D. Silvers P. A. Thompson J. D. Simon Solution photophysics of 1- and 3-aminofluorenone: the role of inter- and intramolecular hydrogen-bonding in radiationless deactivation J. Phys. Chem. 1991 95 8466-8473.
    • (1991) J. Phys. Chem. , vol.95 , pp. 8466-8473
    • Moog, R.S.1    Burozski, N.A.2    Desai, M.M.3    Good, W.R.4    Silvers, C.D.5    Thompson, P.A.6    Simon, J.D.7
  • 6
    • 0036149612 scopus 로고    scopus 로고
    • Excited-state proton transfer: From constrained systems to “Super” photoacids to superfast proton transfer
    • L. M. Tolbert K. M. Solntsev Excited-state proton transfer: from constrained systems to “Super” photoacids to superfast proton transfer Acc. Chem. Res. 2002 35 19-27.
    • (2002) Acc. Chem. Res. , vol.35 , pp. 19-27
    • Tolbert, L.M.1    Solntsev, K.M.2
  • 7
    • 1842531453 scopus 로고    scopus 로고
    • Effect of pressure on proton transfer rate from a photoacid to a solvent. 3. 2-naphthol and 2-naphthol monosulfonate derivatives in water
    • L. Genosar P. Leiderman N. Koifman D. Huppert Effect of pressure on proton transfer rate from a photoacid to a solvent. 3. 2-naphthol and 2-naphthol monosulfonate derivatives in water J. Phys. Chem. A 2004 108 1779-1789.
    • (2004) J. Phys. Chem. A , vol.108 , pp. 1779-1789
    • Genosar, L.1    Leiderman, P.2    Koifman, N.3    Huppert, D.4
  • 8
    • 0006324770 scopus 로고    scopus 로고
    • Conformational Aspects of Intra- and Intermolecular Excited-State Proton Transfer
    • J. Waluk, Wiley-VCH, New York
    • J. Waluk, Conformational Aspects of Intra- and Intermolecular Excited-State Proton Transfer, in Conformational Analysis of Molecules in Excited States, ed. J. Waluk, Wiley-VCH, New York, 2000.
    • (2000) Conformational Analysis of Molecules in Excited States
    • Waluk, J.1
  • 9
    • 0001769521 scopus 로고
    • Excited-state proton transfer reactions. I. Fundamentals and intermolecular reactions
    • L. G. Arnaut S. J. Formosinho Excited-state proton transfer reactions. I. Fundamentals and intermolecular reactions J. Photochem. Photobiol., A 1993 75 1-20.
    • (1993) J. Photochem. Photobiol., A , vol.75 , pp. 1-20
    • Arnaut, L.G.1    Formosinho, S.J.2
  • 10
    • 33845377203 scopus 로고
    • Excited-state proton-transfer reactions and proton-induced quenching of aromatic compounds
    • H. Shizuka Excited-state proton-transfer reactions and proton-induced quenching of aromatic compounds Acc. Chem. Res. 1985 18 141-147.
    • (1985) Acc. Chem. Res. , vol.18 , pp. 141-147
    • Shizuka, H.1
  • 11
  • 12
    • 0004382723 scopus 로고
    • Excited-state proton transfer reactions. II. Intramolecular reactions
    • S. J. Formosinho L. G. Arnaut Excited-state proton transfer reactions. II. Intramolecular reactions J. Photochem. Photobiol., A 1993 75 21-48.
    • (1993) J. Photochem. Photobiol., A , vol.75 , pp. 21-48
    • Formosinho, S.J.1    Arnaut, L.G.2
  • 13
    • 0000840070 scopus 로고
    • Photorotamerization of methyl salicylate and related compounds in cryogenic matrixes
    • E. Orton M. A. Morgan G. C. Pimentel Photorotamerization of methyl salicylate and related compounds in cryogenic matrixes J. Phys. Chem. 1990 94 7936-7943.
    • (1990) J. Phys. Chem. , vol.94 , pp. 7936-7943
    • Orton, E.1    Morgan, M.A.2    Pimentel, G.C.3
  • 14
    • 0000042210 scopus 로고
    • Fluorescence studies of intramolecularly hydrogen-bonded o-hydroxyacetophenone, salicylamide, and related molecules
    • T. Nishiya S. Yamauchi N. Hirota M. Baba I. Hanazaki Fluorescence studies of intramolecularly hydrogen-bonded o-hydroxyacetophenone, salicylamide, and related molecules J. Phys. Chem. 1986 90 5730-5735.
    • (1986) J. Phys. Chem. , vol.90 , pp. 5730-5735
    • Nishiya, T.1    Yamauchi, S.2    Hirota, N.3    Baba, M.4    Hanazaki, I.5
  • 15
    • 0006378850 scopus 로고
    • Femtosecond real-time probing of reactions. IX. Hydrogen atom transfer
    • J. L. Herek S. Pedersen L. Banares A. H. Zewail Femtosecond real-time probing of reactions. IX. Hydrogen atom transfer J. Chem. Phys. 1992 97 9046-9061.
    • (1992) J. Chem. Phys. , vol.97 , pp. 9046-9061
    • Herek, J.L.1    Pedersen, S.2    Banares, L.3    Zewail, A.H.4
  • 16
    • 0000182018 scopus 로고
    • Intramolecular proton transfer in electronically excited molecules
    • W. Klöpffer Intramolecular proton transfer in electronically excited molecules Adv. Photochem. 1977 10 311-358.
    • (1977) Adv. Photochem. , vol.10 , pp. 311-358
    • Klöpffer, W.1
  • 17
    • 0000109965 scopus 로고    scopus 로고
    • Effects of electronic structures on the excited-state intramolecular proton transfer of 1-hydroxy-2-acetonaphthone and related compounds
    • S. Tobita M. Yamamoto N. Kurahayashi R. Tsukagoshi Y. Nakamura H. Shizuka Effects of electronic structures on the excited-state intramolecular proton transfer of 1-hydroxy-2-acetonaphthone and related compounds J. Phys. Chem. A 1998 102 5206-5214.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 5206-5214
    • Tobita, S.1    Yamamoto, M.2    Kurahayashi, N.3    Tsukagoshi, R.4    Nakamura, Y.5    Shizuka, H.6
  • 18
    • 2942695878 scopus 로고    scopus 로고
    • Breaking, making, and twisting of chemical bonds in gas, liquid, and nanocavities
    • A. Douhal Breaking, making, and twisting of chemical bonds in gas, liquid, and nanocavities Acc. Chem. Res. 2004 37 349-355.
    • (2004) Acc. Chem. Res. , vol.37 , pp. 349-355
    • Douhal, A.1
  • 19
    • 21344476427 scopus 로고
    • Excited-state intramolecular proton transfer in jet-cooled 1-hydroxy-2-acetonaphtone
    • A. Douhal F. Lahmani A. Zehnacker-Rentien Excited-state intramolecular proton transfer in jet-cooled 1-hydroxy-2-acetonaphtone Chem. Phys. 1993 178 493-504.
    • (1993) Chem. Phys. , vol.178 , pp. 493-504
    • Douhal, A.1    Lahmani, F.2    Zehnacker-Rentien, A.3
  • 20
  • 21
    • 0242559088 scopus 로고    scopus 로고
    • Temperature and solvent effects on the photodynamics of 1′-hydroxy-2′-acetonaphtone
    • J. A. Organero A. Douhal Temperature and solvent effects on the photodynamics of 1′-hydroxy-2′-acetonaphtone Chem. Phys. Lett. 2003 381 759-765.
    • (2003) Chem. Phys. Lett. , vol.381 , pp. 759-765
    • Organero, J.A.1    Douhal, A.2
  • 22
    • 0011840945 scopus 로고
    • Picosecond fluorescence lifetimes of anthraquinone derivatives. Radiationless deactivation via intra- and intermolecular hydrogen-bonds
    • H. Inoue M. Hida N. Nakashima K. Yoshihara Picosecond fluorescence lifetimes of anthraquinone derivatives. Radiationless deactivation via intra- and intermolecular hydrogen-bonds J. Phys. Chem. 1982 86 3184-3188.
    • (1982) J. Phys. Chem. , vol.86 , pp. 3184-3188
    • Inoue, H.1    Hida, M.2    Nakashima, N.3    Yoshihara, K.4
  • 23
    • 0031244738 scopus 로고    scopus 로고
    • Molecular mechanism of radiationless deactivation of aminoanthraquinones through intermolecular hydrogen-bonding interaction with alcohols and hydroperoxides
    • T. Yatsuhashi H. Inoue Molecular mechanism of radiationless deactivation of aminoanthraquinones through intermolecular hydrogen-bonding interaction with alcohols and hydroperoxides J. Phys. Chem. A 1997 101 8166-8173.
    • (1997) J. Phys. Chem. A , vol.101 , pp. 8166-8173
    • Yatsuhashi, T.1    Inoue, H.2
  • 24
    • 0000774889 scopus 로고    scopus 로고
    • Photophysical properties of intramolecular charge-transfer excited singlet state of aminofluorenone derivatives
    • T. Yatsuhashi Y. Nakajima T. Shimada H. Inoue Photophysical properties of intramolecular charge-transfer excited singlet state of aminofluorenone derivatives J. Phys. Chem. A 1998 102 3018-3024.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 3018-3024
    • Yatsuhashi, T.1    Nakajima, Y.2    Shimada, T.3    Inoue, H.4
  • 25
    • 0001048326 scopus 로고    scopus 로고
    • Molecular mechanism for the radiationless deactivation of the intramolecular charge-transfer excited singlet state of aminofluorenones through hydrogen-bonds with alcohols
    • T. Yatsuhashi Y. Nakajima T. Shimada H. Tachibana H. Inoue Molecular mechanism for the radiationless deactivation of the intramolecular charge-transfer excited singlet state of aminofluorenones through hydrogen-bonds with alcohols J. Phys. Chem. A 1998 102 8657-8663.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 8657-8663
    • Yatsuhashi, T.1    Nakajima, Y.2    Shimada, T.3    Tachibana, H.4    Inoue, H.5
  • 26
    • 0035114936 scopus 로고    scopus 로고
    • The role of intersystem crossing in the deactivation of the singlet excited aminofluorenones
    • L. Biczók T. Bérces T. Yatsuhashi H. Tachibana H. Inoue The role of intersystem crossing in the deactivation of the singlet excited aminofluorenones Phys. Chem. Chem. Phys. 2001 3 980-985.
    • (2001) Phys. Chem. Chem. Phys. , vol.3 , pp. 980-985
    • Biczók, L.1    Bérces, T.2    Yatsuhashi, T.3    Tachibana, H.4    Inoue, H.5
  • 27
    • 0037206705 scopus 로고    scopus 로고
    • Radiationless deactivation process of 1-dimethylamino-9-fluorenone induced by conformational relaxation in the excited state: A new model molecule for the TICT process
    • A. Morimoto L. Biczók T. Yatsuhashi T. Shimada S. Baba H. Tachibana D. A. Tryk H. Inoue Radiationless deactivation process of 1-dimethylamino-9-fluorenone induced by conformational relaxation in the excited state: a new model molecule for the TICT process J. Phys. Chem. A 2002 106 10089-10095.
    • (2002) J. Phys. Chem. A , vol.106 , pp. 10089-10095
    • Morimoto, A.1    Biczók, L.2    Yatsuhashi, T.3    Shimada, T.4    Baba, S.5    Tachibana, H.6    Tryk, D.A.7    Inoue, H.8
  • 29
    • 0001479688 scopus 로고
    • Proximity effect in molecular photophysics: Dynamical consequences of pseudo-Jahn–Teller interaction
    • E. C. Lim Proximity effect in molecular photophysics: dynamical consequences of pseudo-Jahn–Teller interaction J. Phys. Chem. 1986 90 6770-6777.
    • (1986) J. Phys. Chem. , vol.90 , pp. 6770-6777
    • Lim, E.C.1
  • 30
    • 0000453138 scopus 로고
    • Vibrational tuning of the proximity effect in radiationless transitions
    • W. A. Wassam Jr. E. C. Lim Vibrational tuning of the proximity effect in radiationless transitions J. Chem. Phys. 1978 68 433-454.
    • (1978) J. Chem. Phys. , vol.68 , pp. 433-454
    • Wassam, W.A.1    Lim, E.C.2
  • 31
    • 0020417380 scopus 로고
    • Photophysical properties of biologically important molecules related to proximity effects: Psolalens
    • T.-I. Lai B. T. Lim E. C. Lim Photophysical properties of biologically important molecules related to proximity effects: psolalens J. Am. Chem. Soc. 1982 104 7631-7635.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 7631-7635
    • Lai, T.-I.1    Lim, B.T.2    Lim, E.C.3
  • 32
    • 0001293039 scopus 로고
    • Proximity effect and excited-state dynamics of 9-carbonyl-substituted anthracenes
    • T.-I. Lai E. C. Lim Proximity effect and excited-state dynamics of 9-carbonyl-substituted anthracenes J. Am. Chem. Soc. 1985 107 1134-1137.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 1134-1137
    • Lai, T.-I.1    Lim, E.C.2
  • 33
    • 84885393188 scopus 로고
    • Reference materials for fluorescence measurement
    • D. F. Eaton Reference materials for fluorescence measurement Pure Appl. Chem. 1988 60 1107-1114.
    • (1988) Pure Appl. Chem. , vol.60 , pp. 1107-1114
    • Eaton, D.F.1
  • 34
    • 0000653785 scopus 로고    scopus 로고
    • Solvent-dependent radiationless transitions of excited 1-aminonaphtalene derivatives
    • K. Suzuki H. Tanabe S. Tobita H. Shizuka Solvent-dependent radiationless transitions of excited 1-aminonaphtalene derivatives J. Phys. Chem. A 1997 101 4496-4503.
    • (1997) J. Phys. Chem. A , vol.101 , pp. 4496-4503
    • Suzuki, K.1    Tanabe, H.2    Tobita, S.3    Shizuka, H.4
  • 36
    • 0001319296 scopus 로고
    • Isotope multiplets in the carbon-13 nmr spectra of aniline derivatives and nucleosides with partially deuterated amino groups: Effects of intra- and intermolecular hydrogen-bonding
    • J. Reuben Isotope multiplets in the carbon-13 nmr spectra of aniline derivatives and nucleosides with partially deuterated amino groups: effects of intra- and intermolecular hydrogen-bonding J. Am. Chem. Soc. 1987 109 316-321.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 316-321
    • Reuben, J.1
  • 39
    • 0001098929 scopus 로고
    • Direct measurement of the quantum yield of the energy transfer from the higher excited triplet states by the transient thermal lens method
    • M. Terajima T. Azumi Direct measurement of the quantum yield of the energy transfer from the higher excited triplet states by the transient thermal lens method Chem. Phys. Lett. 1987 141 237-240.
    • (1987) Chem. Phys. Lett. , vol.141 , pp. 237-240
    • Terajima, M.1    Azumi, T.2
  • 40
    • 2342526764 scopus 로고
    • Time-resolved photothermal and photoacoustic methods applied to photoinduced processes in solution
    • S. E. Braslavsky G. E. Heibel Time-resolved photothermal and photoacoustic methods applied to photoinduced processes in solution Chem. Rev. 1992 92 1381-1410.
    • (1992) Chem. Rev. , vol.92 , pp. 1381-1410
    • Braslavsky, S.E.1    Heibel, G.E.2
  • 42
    • 33847797571 scopus 로고
    • The solvatochromic comparison method. I. The β-scale of solvent hydrogen-bond acceptor (HBA) basicities
    • R. W. Taft M. J. Kamlet The solvatochromic comparison method. I. The β-scale of solvent hydrogen-bond acceptor (HBA) basicities J. Am. Chem. Soc. 1976 98 2886-2894.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 2886-2894
    • Taft, R.W.1    Kamlet, M.J.2
  • 43
    • 0041573625 scopus 로고
    • Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π*, α, and β, and some methods for simplifying the generalized solvatochromic equation
    • M. J. Kamlet J.-L. Abboud M. H. Abraham R. W. Taft Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π*, α, and β, and some methods for simplifying the generalized solvatochromic equation J. Org. Chem. 1983 48 2877-2887.
    • (1983) J. Org. Chem. , vol.48 , pp. 2877-2887
    • Kamlet, M.J.1    Abboud, J.-L.2    Abraham, M.H.3    Taft, R.W.4
  • 44
    • 36849100924 scopus 로고
    • Radiationless transitions in polyatomic molecules. I. Calculation of Franck–Condon factors
    • W. Siebrand Radiationless transitions in polyatomic molecules. I. Calculation of Franck–Condon factors J. Chem. Phys. 1967 46 440-447.
    • (1967) J. Chem. Phys. , vol.46 , pp. 440-447
    • Siebrand, W.1
  • 45
    • 36849114379 scopus 로고
    • Radiationless transitions in polyatomic molecules. II. Triplet-ground-state transitions in aromatic hydrocarbons
    • W. Siebrand Radiationless transitions in polyatomic molecules. II. Triplet-ground-state transitions in aromatic hydrocarbons J. Chem. Phys. 1967 47 2411-2422.
    • (1967) J. Chem. Phys. , vol.47 , pp. 2411-2422
    • Siebrand, W.1
  • 47
    • 36749105799 scopus 로고
    • Radiationless transitions in aromatic molecules with nonbonding electrons. Role of vibronically active out-of-plane modes
    • N. Kanamaru E. C. Lim Radiationless transitions in aromatic molecules with nonbonding electrons. Role of vibronically active out-of-plane modes J. Chem. Phys. 1975 8 3252-3257.
    • (1975) J. Chem. Phys. , vol.8 , pp. 3252-3257
    • Kanamaru, N.1    Lim, E.C.2
  • 48
    • 0039832023 scopus 로고
    • Radiationless processes involving change of multiplicity in diazenes
    • M. A. El-Sayed Radiationless processes involving change of multiplicity in diazenes J. Chem. Phys. 1962 36 573-574.
    • (1962) J. Chem. Phys. , vol.36 , pp. 573-574
    • El-Sayed, M.A.1
  • 49
    • 36849117004 scopus 로고
    • Spin–orbit coupling and the radiationless processes in nitrogen heterocyclics
    • M. A. El-Sayed Spin–orbit coupling and the radiationless processes in nitrogen heterocyclics J. Chem. Phys. 1963 38 2834-2838.
    • (1963) J. Chem. Phys. , vol.38 , pp. 2834-2838
    • El-Sayed, M.A.1
  • 50
    • 0042070833 scopus 로고
    • Vanishing first- and second-order intramolecular heavy-atom effects on the (π*→n) phosphorescence in carbonyls
    • M. A. El-Sayed Vanishing first- and second-order intramolecular heavy-atom effects on the (π*→n) phosphorescence in carbonyls J. Chem. Phys. 1964 41 2462-2467.
    • (1964) J. Chem. Phys. , vol.41 , pp. 2462-2467
    • El-Sayed, M.A.1
  • 51
    • 17544368479 scopus 로고
    • On a possible excited state proton transfer in N-formylkynurenine derivatives
    • M. P. Pileni P. Walrant R. Santus On a possible excited state proton transfer in N-formylkynurenine derivatives Chem. Phys. Lett. 1976 42 89-92.
    • (1976) Chem. Phys. Lett. , vol.42 , pp. 89-92
    • Pileni, M.P.1    Walrant, P.2    Santus, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.