188-90-9Relevant academic research and scientific papers
The right way to self-fuse bi- and terpyrenyls to afford graphenic cutouts
Lorbach, Dominik,Wagner, Manfred,Baumgarten, Martin,Muellen, Klaus
, p. 10578 - 10580 (2013)
In this work, we subject bi- and terpyrenyls to selective fusion for formation of extended polycyclic aromatic hydrocarbons (PAHs). Connecting the pyrene units at 4-4′- or 1-4′-positions led to smooth formation of extended PAHs, achieved via cyclodehydrog
π-Conjugated benzoperylenes: Sequential C-S bond cleavage and charge distribution patterns of the anions
Benshafrut, Ronnie,Rabinovitz, Mordecai,Hoffman, Roy E.,Ben-Mergui, Naama,Muellen, Klaus,Iyer, Vivekanantan S.
, p. 37 - 48 (2007/10/03)
Chemical reduction of polyaromatic hydrocarbons yielded solutions of long-lived polyanionic species. Reduction of a sulfur heterocycle afforded a stable sulfur-containing dianion. Sulfur extrusion from this dianion proceeded upon further contact with the reducing metal. NMR and UV studies indicate a sulfur extrusion mechanism different than that previously observed in THF. Electron transfer to the already reduced hydrocarbon skeleton results in the stepwise cleavage of the two C-S bonds and the extrusion of a sulfur atom. Dimers of aromatic hydrocarbons such as pyrene and phenanthrene have been reduced as well. The interplay between coulombic repulsions and resonance energies is described.
OXIDATIVE COUPLING OF 9,10-DIHYDROPHENANTHRENE AND POLYNUCLEAR HYDROCARBONS BY ALUMINUM CHLORIDE-CUPRIC CHLORIDE
Guenther, Howard,Kovacic, Peter
, p. 413 - 428 (2007/10/02)
Products from the oxidative coupling of 9,10-dihydrophenanthrene and polynuclear hydrocarbons (phenanthrene and pyrene) with AlCl3-CuCl2 included the respective dehydro dimers and trimers, accompanied by higher oligomers.
Generation of Arenium Ions by a Self-Protonation Reaction in an Aprotic Molten Salt Medium
Buchanan, A. C.,Dworkin, A. S.,Smith, G. P.
, p. 5262 - 5265 (2007/10/02)
We have examined the reaction behavior of a group of polycyclic aromatic hydrocarbons in the aprotic liquid SbCl3-10 mol percent AlCl3 from 100 to 130 deg C by 1H NMR and by quench and separation techniques.For anthracene, pyrene, 9,10-dimethylanthracene, 9,10-diphenylanthracene, and naphthacene, we have observed a novel arene self-protonation reaction for which the proton source is the condensation-dehydrogenation of a portion of the arene combined with arene oxidation by SbCl3.Naphthalene and phenanthrene, however, do not undergo this reaction.Evidence is presented which indicates that the self-protonation reaction proceeds through the oxidation of the arene to its radical cation by SbCl3, and that the function of AlCl3 is to enhance the oxidizing power of the Sb3+/Sb0 couple.
