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Volumn 46, Issue 29, 2007, Pages 5524-5527

Annularly fused hexapyrrolohexaazacoronenes: An extended π system with multiple interior nitrogen atoms displays stable oxidation states

Author keywords

Annulation; Aromaticity; Fused ring systems; Nitrogen heterocycles; Redox chemistry

Indexed keywords

MOLECULAR STRUCTURE; NITROGEN; OXIDATION; SYNTHESIS (CHEMICAL);

EID: 34547228105     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701452     Document Type: Article
Times cited : (141)

References (40)
  • 2
    • 84890987272 scopus 로고    scopus 로고
    • Eds, M. M. Haley, R. R. Tykwinski, Wiley-VCH, Weinheim
    • b) Carbon-Rich Compounds (Eds.: M. M. Haley, R. R. Tykwinski), Wiley-VCH, Weinheim, 2006;
    • (2006) Carbon-Rich Compounds
  • 8
    • 0003714767 scopus 로고    scopus 로고
    • Eds, T. A. Skotheim, R. L. Elsanbaumer, J. R. Reynolds, Marcel Dekker, New York
    • b) Handbook of Con ducting Polymers (Eds.: T. A. Skotheim, R. L. Elsanbaumer, J. R. Reynolds), Marcel Dekker, New York, 1998;
    • (1998) Handbook of Con ducting Polymers
  • 10
  • 20
    • 34547235706 scopus 로고    scopus 로고
    • Hexapyrrolo[2,1,5-bc:2′,1′,5′-ef: 2″,1″,5″-hi:2‴,1‴,5‴-kl: 2‴′,1‴′,5‴′-no:2‴″, 1‴″,5‴″- qr][2a,4a,6a,8a,10a,12a] hexaazacoronene for 2a.
    • Hexapyrrolo[2,1,5-bc:2′,1′,5′-ef: 2″,1″,5″-hi:2‴,1‴,5‴-kl: 2‴′,1‴′,5‴′-no:2‴″, 1‴″,5‴″- qr][2a,4a,6a,8a,10a,12a] hexaazacoronene for 2a.
  • 23
    • 0043114691 scopus 로고    scopus 로고
    • As predicted by simple Hückel theory, 4n π-electron systems are potentially triplet ground states due to orbital degeneracy. However, the orbital degeneracy can be avoided by the Jahn-Teller distortion; for hexaazaoctadecahydrocoronene dication, see: a J. S. Miller, D. A. Dixon, J. C. Calabrese, Science 1988, 240, 1185-1188;
    • As predicted by simple Hückel theory, 4n π-electron systems are potentially triplet ground states due to orbital degeneracy. However, the orbital degeneracy can be avoided by the Jahn-Teller distortion; for hexaazaoctadecahydrocoronene dication, see: a) J. S. Miller, D. A. Dixon, J. C. Calabrese, Science 1988, 240, 1185-1188;
  • 24
    • 0000801759 scopus 로고
    • for hexaiodobenzene dication, see: b
    • for hexaiodobenzene dication, see: b) D. J. Sagl, J. C. Martin, J. Am. Chem. Soc. 1988, 110, 5827-5833;
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 5827-5833
    • Sagl, D.J.1    Martin, J.C.2
  • 25
    • 0011562313 scopus 로고
    • for coronene dication, see: c
    • for coronene dication, see: c) P. J. Krusic, E. Wasserman, J. Am. Chem. Soc. 1991, 113, 2322-2323;
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 2322-2323
    • Krusic, P.J.1    Wasserman, E.2
  • 30
    • 34547160951 scopus 로고    scopus 로고
    • Crystal data for 2c: C114H48F 36N6·2 CH2Cl2, M w, 2355.47, triclinic, space group P1, a, 10.0240(5, b, 17.2079(7, c, 29.5595(9) Å, α, 82.158(1, β, 85.121(1, γ, 82.370(1)°, V, 4994.7(20) Å3, Z, 2, ρcalcd, 1.564 g cm -3, T, 120 K, Data collection with MoKα radiation (Nonius KCCD diffractometer, 66 551 measured reflections, 21 041 unique reflections, Rmerge, 0.0466, 13 363 observed reflections (I > 2.0 σ(I, structure solution by direct methods Shelxs, refinement by full matrix least squares on F with anisotropic temperature factors for the non-H atoms. Final R, 0.0542, Rw, 0.0593, GOF, 0.910;
    • w = 0.0593, GOF = 0.910;
  • 31
    • 34547225738 scopus 로고    scopus 로고
    • Crystal data for dication 2c2, C 114H48Cl12F36N6Sb 2·2 CD2Cl2, Mw, 3028.43, orthorhombic, space group Pbc21 a, 15.8638(5, b, 21.7881(6, c, 32.2727(9) Å, V, 11 154.8(10) Å3, Z, 4, ρcalcd, 1.801 g cm-3, T, 120 K, Data collection with MoKα radiation Nonius KCCD diffractometer, 70 327 measured reflections
    • Kα radiation (Nonius KCCD diffractometer). 70 327 measured reflections,
  • 32
    • 34547152227 scopus 로고    scopus 로고
    • 2+) 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.
    • 2+) 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.
  • 33
    • 0004306024 scopus 로고
    • Eds, O. Hammerich, V. D. Parker, Academic Press, New York
    • Carbon-13 NMR Spectroscopy (Eds.: O. Hammerich, V. D. Parker), Academic Press, New York, 1972.
    • (1972) Carbon-13 NMR Spectroscopy
  • 36
    • 34547191313 scopus 로고    scopus 로고
    • Small bond-length dispersion for each pyrrole could be seen due to the slightly ruffled structure of the HPHAC core.
    • Small bond-length dispersion for each pyrrole could be seen due to the slightly "ruffled" structure of the HPHAC core.


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