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Volumn 49, Issue 39, 2010, Pages 7059-7062

Synthesis, structure, and photophysical properties of dibenzo-[de, mn]naphthacenes

Author keywords

Alkynes; Aromaticity; Cycloaddition; Nickel palladium

Indexed keywords

ALKYNES; AROMATICITIES; BOND ALTERNATION; CYCLOADDUCTS; CYCLODIMERIZATION; ETHYNYL; PHOTOPHYSICAL PROPERTIES; SIX-MEMBERED RINGS; TITLE COMPOUNDS; X-RAY CRYSTAL ANALYSIS;

EID: 77956935446     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201001929     Document Type: Article
Times cited : (84)

References (65)
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    • See the Supporting Information.
    • See the Supporting Information.
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    • The structure of 6 was verified by X-ray crystal analysis (T.-C. Wu, Y.-T. Wu, unpublished results). X-ray crystallographic data for 1a (CCDC762793), 1b (CCDC762790), 1l (CCDC762792), 1r (CCDC762794), 7 (CCDC762791), and 9a(CCDC771823) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • The structure of 6 was verified by X-ray crystal analysis (T.-C. Wu, Y.-T. Wu, unpublished results). X-ray crystallographic data for 1a (CCDC762793), 1b (CCDC762790), 1l (CCDC762792), 1r (CCDC762794), 7 (CCDC762791), and 9a(CCDC771823) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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    • 77956901113 scopus 로고    scopus 로고
    • In the presence of Pd catalysts and silver salts, hexaphenylben- zene undergoes the partial cyclodehydrogenation to generate 1, 2, 3, 4-tetraphenyltriphenylene; see
    • In the presence of Pd catalysts and silver salts, hexaphenylben- zene undergoes the partial cyclodehydrogenation to generate 1, 2, 3, 4-tetraphenyltriphenylene; see
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    • A cycloadduct generated via 1bthrough the full cyclodehydrogenation was not observed. Reviews for Lewis acid-mediated cyclodehydrogenation of polycyclic aromatic hydrocarbons
    • a) Y.-T. Wu, K.-H. Huang, C.-C. Shin, T.-C. Wu, Chem. Eur. J. 2008, 14, 6697. A cycloadduct generated via 1bthrough the full cyclodehydrogenation was not observed. Reviews for Lewis acid-mediated cyclodehydrogenation of polycyclic aromatic hydrocarbons
    • (2008) Chem. Eur. J. , vol.14 , pp. 6697
    • Wu, Y.-T.1    Huang, K.-H.2    Shin, C.-C.3    Wu, T.-C.4
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    • 2) was isolated in 92% yield. Unfortunately, the accurate structure cannot be determined on the basis of 1H and 13C NMR and MS spectra. Crystallization of this compound was not successful because it slowly decomposed
    • 2) was isolated in 92% yield. Unfortunately, the accurate structure cannot be determined on the basis of 1H and 13C NMR and MS spectra. Crystallization of this compound was not successful because it slowly decomposed.
  • 53
    • 77956902762 scopus 로고    scopus 로고
    • Phenanthrene with small displacements from exact planarity
    • Phenanthrene with small displacements from exact planarity
  • 54
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    • Some 4, 5-disubstituted phenanthrenes deviate significantly from planarity
    • a) M. I. Kay, Y. Okaya, D. E. Cox, Acta Crystallogr. Sect. B1971, 27, 26. Some 4, 5-disubstituted phenanthrenes deviate significantly from planarity
    • (1971) Acta Crystallogr. Sect. B , vol.27 , pp. 26
    • Kay, M.I.1    Okaya, Y.2    Cox, D.E.3
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    • 0000166575 scopus 로고
    • 6, 8, 15, 17-Tetraphenyl-1.18, 4.5, 9.10, 13.14-tetrabenzoheptacene, which contains phenanthrene substructures, is a twisted acene
    • d) R. N. Armstrong, H. L. Ammon, J. N. Darnow, J. Am. Chem. Soc. 1987, 109, 2077. 6, 8, 15, 17-Tetraphenyl-1.18, 4.5, 9.10, 13.14-tetrabenzoheptacene, which contains phenanthrene substructures, is a twisted acene
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2077
    • Armstrong, R.N.1    Ammon, H.L.2    Darnow, J.N.3
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    • Bond alternation (or localization) in aromatic systems is also a method to distinguish between benzene and cyclohexatriene. For example, the bond alternation in tris(bicyclo- [2.1.1]hexeno)benzene is estimated to be 0.089 Å
    • Bond alternation (or localization) in aromatic systems is also a method to distinguish between benzene and cyclohexatriene. For example, the bond alternation in tris(bicyclo- [2.1.1]hexeno)benzene is estimated to be 0.089 Å
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    • Epoxidation and cyclopropanation of tris(bicyclo[2.1.1]hexeno)benzene give triexpoxide and tercyclopropane, respectively, see
    • Angew. Chem. Int. Ed. Engl. 1995, 34, 1454. Epoxidation and cyclopropanation of tris(bicyclo[2.1.1]hexeno)benzene give triexpoxide and tercyclopropane, respectively, see
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1454


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