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Volumn 6, Issue 5, 2007, Pages 552-559

Photochromism of phenoxynaphthacenequinones: Diabatic or adiabatic phenyl group transfer?

Author keywords

[No Author keywords available]

Indexed keywords

PHENYL GROUP; QUINONE DERIVATIVE;

EID: 34248137990     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b618661k     Document Type: Article
Times cited : (15)

References (43)
  • 1
    • 34248180972 scopus 로고
    • Problème de constitution dans la série du tetracene
    • C. Marschalk C. Stumm Problème de constitution dans la série du tetracene Bull. Soc. Chim. Fr. 1946 418 428
    • (1946) Bull. Soc. Chim. Fr. , pp. 418-428
    • Marschalk, C.1    Stumm, C.2
  • 2
    • 0000769963 scopus 로고
    • Photoisomerization of 6-phenoxy-5,12-naphthacenequinone
    • engl. transl.: J. Org. Chem. USSR, 1971, 2505-2507
    • Yu. E. Gerasimenko N. T. Poteleshchenko Photoisomerization of 6-phenoxy-5,12-naphthacenequinone Zh. Org. Khim. 1971 7 2413 2415
    • (1971) Zh. Org. Khim. , vol.7 , pp. 2413-2415
    • Gerasimenko Yu., E.1    Poteleshchenko, N.T.2
  • 3
    • 0006333896 scopus 로고
    • Photochromism of peri-aryloxy-p-quinones. Determination of molar absorption coefficients of 6-phenoxy-5,11-naphthacenequinones
    • Yu. E. Gerasimenko A. A. Parshutkin N. T. Poteleshchenko V. P. Poteleshchenko V. V. Romanov Photochromism of peri-aryloxy-p-quinones. Determination of molar absorption coefficients of 6-phenoxy-5,11- naphthacenequinones Zh. Prik. Spektr. 1979 30 954 956
    • (1979) Zh. Prik. Spektr. , vol.30 , pp. 954-956
    • Gerasimenko Yu., E.1    Parshutkin, A.A.2    Poteleshchenko, N.T.3    Poteleshchenko, V.P.4    Romanov, V.V.5
  • 4
    • 0348217643 scopus 로고
    • Spectral-luminescent properties and relative positions of the low-lying π,π* and n,π* levels of molecules of the photoisomerized form of photochromic naphthacenequinone
    • I. L. Belaits N. T. Sokolyuk A. A. Parshutkin L. P. Samsonova Yu. E. Gerasimenko Spectral-luminescent properties and relative positions of the low-lying π,π* and n,π* levels of molecules of the photoisomerized form of photochromic naphthacenequinone Zh. Fiz. Khim. 1986 60 640 645
    • (1986) Zh. Fiz. Khim. , vol.60 , pp. 640-645
    • Belaits, I.L.1    Sokolyuk, N.T.2    Parshutkin, A.A.3    Samsonova, L.P.4    Gerasimenko Yu., E.5
  • 5
    • 0342317055 scopus 로고
    • Mechanism of photoisomerization of phenoxynaphthacenequinones in solution during laser photoexcitation
    • Yu. P. Strokach V. A. Barachevskii N. T. Sokolyuk Yu. E. Gerasimenko Mechanism of photoisomerization of phenoxynaphthacenequinones in solution during laser photoexcitation Khim. Fiz. 1987 6 320 325
    • (1987) Khim. Fiz. , vol.6 , pp. 320-325
    • Strokach Yu., P.1    Barachevskii, V.A.2    Sokolyuk, N.T.3    Gerasimenko Yu., E.4
  • 6
    • 0029788582 scopus 로고    scopus 로고
    • Amperometric Transduction and Amplification of Optical Signals Recorded by a Phenoxynaphthacenequinone Monolayer Electrode: Photochemical and pH-gated Electron Transfer
    • A. Doron M. Portnoy M. Lion-Dagan E. Katz I. Willner Amperometric Transduction and Amplification of Optical Signals Recorded by a Phenoxynaphthacenequinone Monolayer Electrode: Photochemical and pH-gated Electron Transfer J. Am. Chem. Soc. 1996 118 8937 8944
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 8937-8944
    • Doron, A.1    Portnoy, M.2    Lion-Dagan, M.3    Katz, E.4    Willner, I.5
  • 7
    • 0034697556 scopus 로고    scopus 로고
    • Porphyrinic phenoxynaphthacenequinones
    • A. J. Myles N. R. Branda Porphyrinic phenoxynaphthacenequinones Tetrahedron Lett. 2000 41 3785 3788
    • (2000) Tetrahedron Lett. , vol.41 , pp. 3785-3788
    • Myles, A.J.1    Branda, N.R.2
  • 10
    • 0004284861 scopus 로고
    • Consultants Bureau, New York and London
    • A. V. El'tsov, Organic Photochromes, Consultants Bureau, New York and London, 1990, translation edited by J. Whittal
    • (1990) Organic Photochromes
    • El'Tsov, A.V.1
  • 11
    • 33845638124 scopus 로고
    • Photochromism of quinoid compounds: Properties of photo-induced ana-quinones
    • N. P. Gritsan L. S. Klimenko Photochromism of quinoid compounds: properties of photo-induced ana-quinones J. Photochem. Photobiol., A 1993 70 103 117
    • (1993) J. Photochem. Photobiol., a , vol.70 , pp. 103-117
    • Gritsan, N.P.1    Klimenko, L.S.2
  • 15
    • 84855703343 scopus 로고
    • Diabatic and adiabatic processes in photochemistry
    • Th. Förster Diabatic and adiabatic processes in photochemistry Pure Appl. Chem. 1970 24 443 449
    • (1970) Pure Appl. Chem. , vol.24 , pp. 443-449
    • Förster, Th.1
  • 17
    • 84986405925 scopus 로고
    • Photoisomerization Pathways of 8,16-Methano[2.2]metacyclophane-1,9-diene. a Model Case for Adiabatic Electrocyclic Ring Closure in the Excited Singlet State
    • J. Wirz G. Persy E. Rommel I. Murata K. Nakasuji Photoisomerization Pathways of 8,16-Methano[2.2]metacyclophane-1,9-diene. A Model Case for Adiabatic Electrocyclic Ring Closure in the Excited Singlet State Helv. Chim. Acta 1984 67 305 317
    • (1984) Helv. Chim. Acta , vol.67 , pp. 305-317
    • Wirz, J.1    Persy, G.2    Rommel, E.3    Murata, I.4    Nakasuji, K.5
  • 18
    • 0027561375 scopus 로고
    • Synthesis of New Photochromic Polymers Based on Phenoxynaphthacenequinone
    • F. Buchholtz A. Zelichenok V. Krongauz Synthesis of New Photochromic Polymers Based on Phenoxynaphthacenequinone Macromolecules 1993 26 906 910
    • (1993) Macromolecules , vol.26 , pp. 906-910
    • Buchholtz, F.1    Zelichenok, A.2    Krongauz, V.3
  • 19
    • 0010349744 scopus 로고
    • Photochromism of peri-arylhydroxy-p-quinones. Synthesis of some substituted phenoxynaphthacenequinones
    • (engl. transl.);
    • Yu. E. Gerasimenko N. T. Poteleshchenko V. V. Romanov Photochromism of peri-arylhydroxy-p-quinones. Synthesis of some substituted phenoxynaphthacenequinones Zh. Org. Khim. 1980 16 1938 1945
    • (1980) Zh. Org. Khim. , vol.16 , pp. 1938-1945
    • Gerasimenko Yu., E.1    Poteleshchenko, N.T.2    Romanov, V.V.3
  • 21
    • 0001177789 scopus 로고
    • Chemical actinometry in the UV by azobenzene in concentrated solution: A convenient method
    • G. Gauglitz S. Hubig Chemical actinometry in the UV by azobenzene in concentrated solution: A convenient method J. Photochem. 1985 30 121 125
    • (1985) J. Photochem. , vol.30 , pp. 121-125
    • Gauglitz, G.1    Hubig, S.2
  • 22
    • 0000536861 scopus 로고
    • Singlet and Triplet Biradical Intermediates in the Valence Isomerization of 2,7-Dihydro-2,2,7,7-tetramethylpyrene
    • E. Hasler A. Hörmann G. Persy H. Platsch J. Wirz Singlet and Triplet Biradical Intermediates in the Valence Isomerization of 2,7-Dihydro-2,2,7,7- tetramethylpyrene J. Am. Chem. Soc. 1993 115 5400 5409
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 5400-5409
    • Hasler, E.1    Hörmann, A.2    Persy, G.3    Platsch, H.4    Wirz, J.5
  • 23
    • 0000163726 scopus 로고
    • Photoacoustic calorimetry: A new cell design and improved analysis algorithms
    • L. A. Melton T. Ni Q. Lu Photoacoustic calorimetry: a new cell design and improved analysis algorithms Rev. Sci. Instrum. 1989 60 3217 3223
    • (1989) Rev. Sci. Instrum. , vol.60 , pp. 3217-3223
    • Melton, L.A.1    Ni, T.2    Lu, Q.3
  • 24
    • 33845182889 scopus 로고
    • The relaxed and spectroscopic energies of olefin triplets
    • T. Ni R. A. Caldwell L. A. Melton The relaxed and spectroscopic energies of olefin triplets J. Am. Chem. Soc. 1989 111 457 464
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 457-464
    • Ni, T.1    Caldwell, R.A.2    Melton, L.A.3
  • 25
    • 33749991777 scopus 로고    scopus 로고
    • Photochemistry of 2-Alkoxymethyl-5-methylphenacyl Chloride and Benzoate
    • L. Plistil T. Solomek J. Wirz D. Heger P. Klan Photochemistry of 2-Alkoxymethyl-5-methylphenacyl Chloride and Benzoate J. Org. Chem. 2006 71 8050 8058
    • (2006) J. Org. Chem. , vol.71 , pp. 8050-8058
    • Plistil, L.1    Solomek, T.2    Wirz, J.3    Heger, D.4    Klan, P.5
  • 26
    • 13444312005 scopus 로고    scopus 로고
    • 2,5-Photochemical reaction mechanisms of 2-nitrobenzyl compounds: 2-Nitrobenzyl alcohols form 2-nitroso hydrates by dual proton transfer
    • M. Gaplovsky Y. V. Il'ichev Y. Kamdzhilov S. Kombarova M. Mac M. A. Schwörer J. Wirz 2,5-Photochemical reaction mechanisms of 2-nitrobenzyl compounds: 2-Nitrobenzyl alcohols form 2-nitroso hydrates by dual proton transfer Photochem. Photobiol. Sci. 2005 4 33 42
    • (2005) Photochem. Photobiol. Sci. , vol.4 , pp. 33-42
    • Gaplovsky, M.1    Il'Ichev, Y.V.2    Kamdzhilov, Y.3    Kombarova, S.4    Mac, M.5    Schwörer, M.A.6    Wirz, J.7
  • 27
    • 0030500058 scopus 로고    scopus 로고
    • Photochromic Properties of Thermally Irreversible 6-Aryloxy-5,12- naphthacenequinones
    • Y. Yokoyama S. Fukui Y. Yokoyama Photochromic Properties of Thermally Irreversible 6-Aryloxy-5,12-naphthacenequinones Chem. Lett. 1996 1996 355 356
    • (1996) Chem. Lett. , vol.1996 , pp. 355-356
    • Yokoyama, Y.1    Fukui, S.2    Yokoyama, Y.3
  • 29
    • 0039777528 scopus 로고
    • Conjugated Radicals I. Introductory Remarks and Methods of calculation
    • R. Zahradnik P. Carsky Conjugated Radicals I. Introductory Remarks and Methods of calculation J. Phys. Chem. 1970 74 1235 1239
    • (1970) J. Phys. Chem. , vol.74 , pp. 1235-1239
    • Zahradnik, R.1    Carsky, P.2
  • 30
    • 0000550050 scopus 로고
    • Conjugated Radicals III. Calculations of Electronic Spectra of Alternant Odd Radicals of the Allyl, Benzyl, and Phenalenyl Types
    • R. Zahradnik P. Carsky Conjugated Radicals III. Calculations of Electronic Spectra of Alternant Odd Radicals of the Allyl, Benzyl, and Phenalenyl Types J. Phys. Chem. 1970 74 1249 1254
    • (1970) J. Phys. Chem. , vol.74 , pp. 1249-1254
    • Zahradnik, R.1    Carsky, P.2
  • 31
    • 0014575322 scopus 로고
    • Triplet states of some common photosensitizing dyes
    • R. W. Chambers D. R. Kearns Triplet states of some common photosensitizing dyes Photochem. Photobiol. 1969 10 215 219
    • (1969) Photochem. Photobiol. , vol.10 , pp. 215-219
    • Chambers, R.W.1    Kearns, D.R.2
  • 32
    • 0021485270 scopus 로고
    • Spectroscopic and kinetic investigations of conjugated biradical intermediates
    • J. Wirz Spectroscopic and kinetic investigations of conjugated biradical intermediates Pure Appl. Chem. 1984 56 1289 1300
    • (1984) Pure Appl. Chem. , vol.56 , pp. 1289-1300
    • Wirz, J.1
  • 33
    • 0033552267 scopus 로고    scopus 로고
    • 1,3-Cyclopentanediyl Diradicals: Substituent and Temperature Dependence of Triplet-Singlet Intersystem Crossing
    • F. Kita W. Adam P. Jordan W. M. Nau J. Wirz 1,3-Cyclopentanediyl Diradicals: Substituent and Temperature Dependence of Triplet-Singlet Intersystem Crossing J. Am. Chem. Soc. 1999 121 9265 9275
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9265-9275
    • Kita, F.1    Adam, W.2    Jordan, P.3    Nau, W.M.4    Wirz, J.5
  • 35
    • 0037657978 scopus 로고    scopus 로고
    • Photohydration of Benzophenone in Aqueous Acid
    • M. Ramseier P. Senn J. Wirz Photohydration of Benzophenone in Aqueous Acid J. Phys. Chem. A 2003 107 3305 3315
    • (2003) J. Phys. Chem. a , vol.107 , pp. 3305-3315
    • Ramseier, M.1    Senn, P.2    Wirz, J.3
  • 37
    • 0030738148 scopus 로고    scopus 로고
    • Laser Flash Photolysis Study of the Reaction Mechanism in the Photochromism of 1-(Acyloxy)-2-methoxyanthraquinones
    • N. P. Gritsan A. Kellmann F. Tfibel L. S. Klimenko Laser Flash Photolysis Study of the Reaction Mechanism in the Photochromism of 1-(Acyloxy)-2- methoxyanthraquinones J. Phys. Chem. A 1997 101 794 801
    • (1997) J. Phys. Chem. a , vol.101 , pp. 794-801
    • Gritsan, N.P.1    Kellmann, A.2    Tfibel, F.3    Klimenko, L.S.4
  • 38
    • 36749105653 scopus 로고
    • Intensity dependence in laser flash photolysis experiments: Hydrated electron formation from ferrocyanide, tyrosine, and tryptophan
    • U. Lachish A. Shafferman G. Stein Intensity dependence in laser flash photolysis experiments: Hydrated electron formation from ferrocyanide, tyrosine, and tryptophan J. Chem. Phys. 1976 64 4205 4211
    • (1976) J. Chem. Phys. , vol.64 , pp. 4205-4211
    • Lachish, U.1    Shafferman, A.2    Stein, G.3
  • 39
    • 0001570928 scopus 로고
    • Über die Elektronenspektren der Acenchinone
    • M. Zander Über die Elektronenspektren der Acenchinone Ber. Bunsen-Ges. Phys. Chem. 1967 71 424 429
    • (1967) Ber. Bunsen-Ges. Phys. Chem. , vol.71 , pp. 424-429
    • Zander, M.1
  • 40
    • 0000564579 scopus 로고
    • Comprehensive Absorption/Chemical, and Theoretical Study of 2-5-Ring Aromatic Hydrocarbon Diones
    • R. S. Becker L. V. Natarajan Comprehensive Absorption/Chemical, and Theoretical Study of 2-5-Ring Aromatic Hydrocarbon Diones J. Phys. Chem. 1993 97 344 349
    • (1993) J. Phys. Chem. , vol.97 , pp. 344-349
    • Becker, R.S.1    Natarajan, L.V.2
  • 41
    • 0038476227 scopus 로고    scopus 로고
    • Photochemical properties of the triplet π,π* state, anion, and ketyl radicals of 5,12-naphthacenequinone in solution studied by laser flash photolysis: Electron transfer and phenolic H-atom transfer
    • M. Yamaji T. Itoh S. Tobita Photochemical properties of the triplet π,π* state, anion, and ketyl radicals of 5,12-naphthacenequinone in solution studied by laser flash photolysis: electron transfer and phenolic H-atom transfer Photochem. Photobiol. Sci. 2002 1 869 876
    • (2002) Photochem. Photobiol. Sci. , vol.1 , pp. 869-876
    • Yamaji, M.1    Itoh, T.2    Tobita, S.3


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