- Chrysene-Based Blue Emitters
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Chrysene and its bisbenzannulated homologue, naphtho[2,3-c]tetraphene, were synthesized through a PtCl2-catalyzed cyclization of alkynes, which also furnished corresponding biaryls subsequent to a Glaser coupling reaction of the starting alkynes. The optoelectronic properties of 5,5′-bichrysenyl and 6,6′-binaphtho[2,3-c]tetraphene were compared to their chrysene-based “monomers”. Oxidative cyclodehydrogenations of bichrysenyl and its higher homologue towards large nanographenes were also investigated.
- Nathusius, Marvin,Ejlli, Barbara,Rominger, Frank,Freudenberg, Jan,Bunz, Uwe H. F.,Müllen, Klaus
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supporting information
p. 15089 - 15093
(2020/10/21)
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- OXIDATION OF ARENES BY MOLTEN GALLIUM(III) CHLORIDE
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Molten, anhydrous Ga2Cl6 at 100-130 deg C readily oxidizes pyrene, anthracene and naphthacene with the concomitant reduction of Ga(III) to Ga(I).Dilute solutions of these arenes (ArH) are oxidized to their radical cations (ArH+.), wich decay very slowly in Ga2Cl6, while more concentrated solutions are oxidized to stable arenium ions (ArH2+) with hydrogen derived from aryl-aryl coupling reactions.
- Dworkin, A. S.,Brown, L. L.,Buchanan, A. C.,Smith, G. P.
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p. 2727 - 2730
(2007/10/02)
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- Twin Annulation of Naphthalene via a 1,5-Naphthodiyne Synthon. New Syntheses of Chrysene and Dibenzochrysene
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New, efficient syntheses of chrysene (1), dibenzochrysene (16), and derivatives are described that feature, as the key step, the formal cycloaddition between 1,5-naphthodiyne (3) and a heterocyclic diene (furan, pyrroles, isoindoles).Subsequent manipulation affords the arene in 26-49percent overall yield from commercially available 2,6-dibromo-1,5-dihydroxynaphthalene (5).The latter is easily converted to ditosylate 6, which, with phenyllithium, serves as a synthon for 3.
- LeHoullier, Craig S.,Gribble, Gordon W.
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p. 1682 - 1685
(2007/10/02)
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