메뉴 건너뛰기




Volumn 3, Issue 7, 2004, Pages 689-694

Photocyclization of trans-1-(1′-naphthyl)-2-(3-hydroxyphenyl)ethene: Evidence for adiabatic 1trans*→1cis* Photoisomerization

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CHRYSENE DERIVATIVE; CYCLOHEXANE; ETHYLENE DERIVATIVE; SOLVENT;

EID: 4344619138     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b404308a     Document Type: Article
Times cited : (14)

References (44)
  • 2
    • 84943492187 scopus 로고
    • Photophysical and photochemical behaviour of stilbene-like molecules and their aza-analogues
    • U. Mazzucato Photophysical and photochemical behaviour of stilbene-like molecules and their aza-analogues Pure Appl. Chem. 1982 54 1705-1721.
    • (1982) Pure Appl. Chem. , vol.54 , pp. 1705-1721
    • Mazzucato, U.1
  • 3
    • 37049075714 scopus 로고
    • Effect of the nature of the aromatic groups on the lowest excited states of trans-1,2-diarylethenes
    • G. Bartocci U. Mazzucato A. Spalletti G. Orlandi G. Poggi Effect of the nature of the aromatic groups on the lowest excited states of trans-1,2-diarylethenes. J. Chem. Soc., Faraday Trans. 1992 88 3139-3144.
    • (1992) J. Chem. Soc., Faraday Trans. , vol.88 , pp. 3139-3144
    • Bartocci, G.1    Mazzucato, U.2    Spalletti, A.3    Orlandi, G.4    Poggi, G.5
  • 4
    • 77951504407 scopus 로고
    • Cis-trans photoisomerization of 1,2-diarylethylenes: Effect of charge transfer interactions
    • U. Mazzucato G. G. Aloisi F. Elisei Cis-trans photoisomerization of 1,2-diarylethylenes: effect of charge transfer interactions Proc. Indian Acad. Sci., Chem. Sci. 1993 105 475-486.
    • (1993) Proc. Indian Acad. Sci., Chem. Sci. , vol.105 , pp. 475-486
    • Mazzucato, U.1    Aloisi, G.G.2    Elisei, F.3
  • 5
    • 0001380711 scopus 로고
    • One-way photoisomerization between cis- and trans-olefin. A novel adiabatic process in the excited state
    • T. Arai T. Karatsu H. Sakuragi K. Tokumaru “One-way” photoisomerization between cis- and trans-olefin. A novel adiabatic process in the excited state Tetrahedron Lett. 1983 24 2873-2876.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 2873-2876
    • Arai, T.1    Karatsu, T.2    Sakuragi, H.3    Tokumaru, K.4
  • 6
    • 4143061335 scopus 로고
    • Photochemical one-way adiabatic isomerization of aromatic olefins
    • T. Arai K. Tokumaru Photochemical one-way adiabatic isomerization of aromatic olefins Chem. Rev. 1993 93 23-39.
    • (1993) Chem. Rev. , vol.93 , pp. 23-39
    • Arai, T.1    Tokumaru, K.2
  • 7
    • 0000208579 scopus 로고
    • Adiabatic photochemical isomerization of cis-1-(9-anthryl)-2-phenylethylene
    • K. Sandros H.-D. Becker Adiabatic photochemical isomerization of cis-1-(9-anthryl)-2-phenylethylene J. Photochem. 1987 39 301-315.
    • (1987) J. Photochem. , vol.39 , pp. 301-315
    • Sandros, K.1    Becker, H.-D.2
  • 8
    • 0000044134 scopus 로고
    • Unimolecular photochemistry of anthracenes
    • H.-D. Becker Unimolecular photochemistry of anthracenes Chem. Rev. 1993 93 145-172.
    • (1993) Chem. Rev. , vol.93 , pp. 145-172
    • Becker, H.-D.1
  • 10
    • 0001765568 scopus 로고
    • The temperature and medium dependencies of cis-stilbene fluorescence. The energetics of twisting in the lowest excited singlet state
    • J. Saltiel A. S. Waller D. F. Sears Jr The temperature and medium dependencies of cis-stilbene fluorescence. The energetics of twisting in the lowest excited singlet state J. Am. Chem. Soc. 1993 115 2453-2465.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 2453-2465
    • Saltiel, J.1    Waller, A.S.2    Sears, D.F.3
  • 11
    • 33845279344 scopus 로고
    • Regioselective trans–cis, photoisomerization of m-styrylstilbenes
    • Y. Ito Y. Uozu T. Dote M. Ueda T. Matsuura Regioselective trans–cis, photoisomerization of m-styrylstilbenes J. Am. Chem. Soc. 1988 110 189-198.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 189-198
    • Ito, Y.1    Uozu, Y.2    Dote, T.3    Ueda, M.4    Matsuura, T.5
  • 12
    • 0025033731 scopus 로고
    • Cis–trans Photoisomerization of p-styrylstilbene, a one- and twofold adiabatic process
    • K. Sandros M. Sundahl O. Wennerström U. Norinder cis–trans Photoisomerization of p-styrylstilbene, a one- and twofold adiabatic process J. Am. Chem. Soc. 1990 112 3082-3086.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 3082-3086
    • Sandros, K.1    Sundahl, M.2    Wennerström, O.3    Norinder, U.4
  • 13
    • 0010875909 scopus 로고
    • Decay pathways of the first excited singlet state of cis-1-styrylpyrene
    • A. Spalletti G. Bartocci U. Mazzucato G. Galiazzo Decay pathways of the first excited singlet state of cis-1-styrylpyrene Chem. Phys. Lett. 1991 186 297-302.
    • (1991) Chem. Phys. Lett. , vol.186 , pp. 297-302
    • Spalletti, A.1    Bartocci, G.2    Mazzucato, U.3    Galiazzo, G.4
  • 14
    • 0010806948 scopus 로고
    • Evidence for adiabatic channels in the singlet photoisomerization of cis-1,2-diarylethenes
    • U. Mazzucato A. Spalletti G. Bartocci G. Galiazzo Evidence for adiabatic channels in the singlet photoisomerization of cis-1,2-diarylethenes Coord. Chem. Rev. 1993 125 251-260.
    • (1993) Coord. Chem. Rev. , vol.125 , pp. 251-260
    • Mazzucato, U.1    Spalletti, A.2    Bartocci, G.3    Galiazzo, G.4
  • 15
    • 0035253011 scopus 로고    scopus 로고
    • Photophysics and photochemistry of the EE, and ZE, isomers of 1-(N-pyridyl)-4-phenyl-1,3 butadiene (n = 2, 3 and 4)
    • Adiabatic trans→cis, isomerization was reported to occur by irradiation of all-trans, 1-(2-pyridyl)-4-phenyl-1,3 butadiene in non polar solvent by:, We thank one of the referees for drawing our attention to this article
    • Adiabatic trans→cis, isomerization was reported to occur by irradiation of all-trans, 1-(2-pyridyl)-4-phenyl-1,3 butadiene in non polar solvent by: G. Bartocci G. Galiazzo U. Mazzucato A. Spalletti Photophysics and photochemistry of the EE, and ZE, isomers of 1-(n-pyridyl)-4-phenyl-1,3 butadiene (n = 2, 3 and 4) Phys. Chem. Chem. Phys. 2001 3 379-86. We thank one of the referees for drawing our attention to this article.
    • (2001) Phys. Chem. Chem. Phys. , vol.3 , pp. 379-386
    • Bartocci, G.1    Galiazzo, G.2    Mazzucato, U.3    Spalletti, A.4
  • 18
    • 0000887799 scopus 로고
    • A new sensitive chemical actinometer. II Potassium ferrioxalate as a standard chemical actinometer
    • C. G. Hatchard C. A. Parker A new sensitive chemical actinometer. II Potassium ferrioxalate as a standard chemical actinometer Proc. R. Soc. London, Ser. A 1956 235 518-536.
    • (1956) Proc. R. Soc. London, Ser. A , vol.235 , pp. 518-536
    • Hatchard, C.G.1    Parker, C.A.2
  • 19
    • 49549166173 scopus 로고
    • Direct and anthraquinone sensitized cis–trans photoisomerization of α and β styrylnaphthalenes
    • P. Bortolus G. Galiazzo Direct and anthraquinone sensitized cis–trans photoisomerization of α and β styrylnaphthalenes J. Photochem. 1973/4 2 361-370.
    • (1973) J. Photochem. , vol.2 , pp. 361-370
    • Bortolus, P.1    Galiazzo, G.2
  • 20
    • 37049129071 scopus 로고
    • Synthesis, electronic spectra and photoisomerization of naphthylpyridylethylenes
    • G. Galiazzo P. Bortolus F. Masetti Synthesis, electronic spectra and photoisomerization of naphthylpyridylethylenes J. Chem. Soc., Perkin Trans. 2 1975 1712-1716.
    • (1975) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1712-1716
    • Galiazzo, G.1    Bortolus, P.2    Masetti, F.3
  • 21
    • 27944492581 scopus 로고
    • Electronic spectra of stilbene and its naphthyl analog
    • G. Wettermark L. Tegnèr O. Martensson Electronic spectra of stilbene and its naphthyl analog Arkiv. Kemi. 1968 80 185-212.
    • (1968) Arkiv. Kemi. , vol.80 , pp. 185-212
    • Wettermark, G.1    Tegnèr, L.2    Martensson, O.3
  • 22
    • 0003157106 scopus 로고
    • Photochemistry of stilbenes. VI. Steric effects on the photocyclizations of some meta-substituted stilbenes
    • F. B. Mallory C. W. Mallory Photochemistry of stilbenes. VI. Steric effects on the photocyclizations of some meta-substituted stilbenes J. Am. Chem. Soc. 1972 94 6041-6048.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 6041-6048
    • Mallory, F.B.1    Mallory, C.W.2
  • 23
    • 33947092457 scopus 로고
    • Conformational equilibria in 1,2-diarylethylenes manifested in their emission spectra and lifetimes
    • E. Haas G. Fischer E. Fischer Conformational equilibria in 1,2-diarylethylenes manifested in their emission spectra and lifetimes J. Phys. Chem. 1978 82 1638-1643.
    • (1978) J. Phys. Chem. , vol.82 , pp. 1638-1643
    • Haas, E.1    Fischer, G.2    Fischer, E.3
  • 24
    • 0001303295 scopus 로고
    • On the mechanism of photochemical cis–trans isomerization
    • H. Stegemeyer On the mechanism of photochemical cis–trans isomerization J. Phys. Chem. 1962 66 2555-2560.
    • (1962) J. Phys. Chem. , vol.66 , pp. 2555-2560
    • Stegemeyer, H.1
  • 26
    • 0001765568 scopus 로고
    • The temperature and medium dependencies of cis-stilbene fluorescence. The energetics for twisting in the lowest excited singlet state
    • J. Saltiel A. S. Waller D. F. Sears Jr. The temperature and medium dependencies of cis-stilbene fluorescence. The energetics for twisting in the lowest excited singlet state J. Am. Chem. Soc. 1993 115 2453-2465.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 2453-2465
    • Saltiel, J.1    Waller, A.S.2    Sears, D.F.3
  • 27
    • 0035123934 scopus 로고    scopus 로고
    • The photochemistry of cis-ortho-, meta-, and para-aminostilbenes
    • F. D. Lewis R. S. Kalgutkar The photochemistry of cis-ortho-, meta-, and para-aminostilbenes J. Phys. Chem. A 2001 105 285-289.
    • (2001) J. Phys. Chem. A , vol.105 , pp. 285-289
    • Lewis, F.D.1    Kalgutkar, R.S.2
  • 29
    • 2842535724 scopus 로고
    • Photochemisty of stilbenes. III. Some aspects of the mechanism of photocyclization to phenanthrenes
    • references therein
    • F. B. Mallory C. S. Wood J. T. Gordon Photochemisty of stilbenes. III. Some aspects of the mechanism of photocyclization to phenanthrenes J. Am. Chem. Soc. 1964 86 3094-3102 and references therein.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 3094-3102
    • Mallory, F.B.1    Wood, C.S.2    Gordon, J.T.3
  • 30
    • 33947488413 scopus 로고
    • Photochemistry of stilbenes. IV. The preparation of substituted phenanthrenes
    • C. S. Wood F. B. Mallory Photochemistry of stilbenes. IV. The preparation of substituted phenanthrenes J. Org. Chem. 1964 29 3373-3377.
    • (1964) J. Org. Chem. , vol.29 , pp. 3373-3377
    • Wood, C.S.1    Mallory, F.B.2
  • 31
    • 84981620237 scopus 로고
    • Photochemical cyclizations and intramolecular cycloadditions of conjugated arylolefins. Part I: Photocyclization with dehydrogenation
    • W. H. Laarhoven Photochemical cyclizations and intramolecular cycloadditions of conjugated arylolefins. Part I: Photocyclization with dehydrogenation Recl. Trav. Chim. Pays-Bas 1983 102 185-204.
    • (1983) Recl. Trav. Chim. Pays-Bas , vol.102 , pp. 185-204
    • Laarhoven, W.H.1
  • 32
    • 84981575426 scopus 로고
    • Part II Photocyclizations without dehydrogenation and photocycloaddition
    • W. H. Laarhoven Part II Photocyclizations without dehydrogenation and photocycloaddition Recl. Trav. Chim. Pays-Bas 1983 102 241-254.
    • (1983) Recl. Trav. Chim. Pays-Bas , vol.102 , pp. 241-254
    • Laarhoven, W.H.1
  • 33
    • 0004545536 scopus 로고
    • Zum mechanismus der photochemischercycliezierung von cis-stilbene
    • H. Güsten L. Klasinc Zum mechanismus der photochemischercycliezierung von cis-stilbene Tetrahedron 1968 24 5499-5507.
    • (1968) Tetrahedron , vol.24 , pp. 5499-5507
    • Güsten, H.1    Klasinc, L.2
  • 34
    • 0000459459 scopus 로고
    • Photodehydrocyclizations of stilbene-like compounds. VI. Chemical evidence of an excited state mechanism
    • T. J. Cuppen W. H. Laarhoven Photodehydrocyclizations of stilbene-like compounds. VI. Chemical evidence of an excited state mechanism J. Am. Chem. Soc. 1972 94 5914-5915.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 5914-5915
    • Cuppen, T.J.1    Laarhoven, W.H.2
  • 36
    • 0017067188 scopus 로고
    • Photocyclization of diethylstilbestrol. Isolation of a stable, self-trapping dihydrophenanthrene intermediate
    • T. D. Doyle W. R. Benson N. Filipescu Photocyclization of diethylstilbestrol. Isolation of a stable, self-trapping dihydrophenanthrene intermediate J. Am. Chem. Soc. 1976 98 3262-3267.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 3262-3267
    • Doyle, T.D.1    Benson, W.R.2    Filipescu, N.3
  • 38
    • 0002238999 scopus 로고
    • The photocyclization of stilbene
    • O. L. Chapman, Marcel Dekker Inc., New York
    • F. R. Stermitz, The photocyclization of stilbene, in Organic Photochemistry, ed. O. L. Chapman, Marcel Dekker Inc., New York, 1967, vol. 1, pp. 248–282.
    • (1967) Organic Photochemistry , vol.1 , pp. 248-282
    • Stermitz, F.R.1
  • 39
    • 0000707492 scopus 로고
    • Conformer-specific adiabatic cis→trans photoisomerization of cis-1-(2-naphthyl)-2-phenylethene. A striking application of the NEER principle
    • J. Saltiel N. Tarkalanov D. F. Sears Jr Conformer-specific adiabatic cis→trans photoisomerization of cis-1-(2-naphthyl)-2-phenylethene. A striking application of the NEER principle J. Am. Chem. Soc. 1995 117 5586-5587.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5586-5587
    • Saltiel, J.1    Tarkalanov, N.2    Sears, D.F.3
  • 40
    • 0009328195 scopus 로고
    • Role of the charge transfer interactions in photoreactions. 1. Exciplexes between styrylnaphthalenes and amines
    • G. G. Aloisi U. Mazzucato J. B. Birks L. Minuti Role of the charge transfer interactions in photoreactions. 1. Exciplexes between styrylnaphthalenes and amines J. Am. Chem. Soc. 1977 99 6340-6347.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 6340-6347
    • Aloisi, G.G.1    Mazzucato, U.2    Birks, J.B.3    Minuti, L.4
  • 41
    • 0000774965 scopus 로고
    • Analysis of the decay of 1-phenyl-2-(2-naphthyl)ethene triplets. A nanosecond laser pulse study
    • H. Görner D. W. Eaker J. Saltiel Analysis of the decay of 1-phenyl-2-(2-naphthyl)ethene triplets. A nanosecond laser pulse study J. Am. Chem. Soc. 1981 103 7164-7169.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 7164-7169
    • Görner, H.1    Eaker, D.W.2    Saltiel, J.3
  • 42
    • 4344693561 scopus 로고
    • Picosecond spectroscopy of phenylnaphthylethylenes
    • S. A. Krysanov M. V. Alfimov Picosecond spectroscopy of phenylnaphthylethylenes Chem. Phys. Lett. 1983 98 176-178.
    • (1983) Chem. Phys. Lett. , vol.98 , pp. 176-178
    • Krysanov, S.A.1    Alfimov, M.V.2
  • 43
    • 0039837708 scopus 로고
    • Triplet state of α-naphthylethylene derivatives. Structural effects on the equilibrium between planar and perpendicular triplet conformations
    • S. Lazare R. Bonneau R. Lapouyade Triplet state of α-naphthylethylene derivatives. Structural effects on the equilibrium between planar and perpendicular triplet conformations J. Phys. Chem. 1984 88 18-23.
    • (1984) J. Phys. Chem. , vol.88 , pp. 18-23
    • Lazare, S.1    Bonneau, R.2    Lapouyade, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.