5101-26-8Relevant academic research and scientific papers
Studies on pyrene and perylene derivatives upon oxidation and application to a higher analogue
Matsumoto, Akinobu,Suzuki, Mitsuharu,Hayashi, Hironobu,Kuzuhara, Daiki,Yuasa, Junpei,Kawai, Tsuyoshi,Aratani, Naoki,Yamada, Hiroko
, p. 667 - 677 (2017)
The structure and electronic features of neutral and positively charged pyrene and perylene derivatives were explored. The radical cation of 1,3,6,8-tetraarylpyrene 1 was examined by ESR, UVvisNIR spectroscopy and theoretical calculations. The addition of
Nickel-Catalyzed Formal Homocoupling of Methoxyarenes for the Synthesis of Symmetrical Biaryls via C-O Bond Cleavage
Nakamura, Keisuke,Tobisu, Mamoru,Chatani, Naoto
supporting information, p. 6142 - 6145 (2016/01/09)
A new method has been developed for the nickel-catalyzed homocoupling of methoxyarenes via C-O bond cleavage using a diboron reagent. The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand was found to be critical to the success of the reaction. This new method allows the synthesis of a wide range of biaryl compounds.
Nickel-catalyzed coupling of aryl bromides in the presence of alkyllithium reagents
Jhaveri, Sarav B.,Carter, Kenneth R.
supporting information; experimental part, p. 6845 - 6848 (2009/07/10)
An easy approach towards the synthesis of compounds using coupling reactions of bromide compounds was demonstrated. A comparison of different alkyllithium reagents was made by examining the coupling of bromobenzene (1a). The molar ratio of bromobenzene to catalyst was 138:1 using [NiCl 2(dppp)] and bromobenzene, Bpy was added to the reaction solution as a ligand. Alkyllithium was added at half molar equivalents to that of phenyl bromide groups with the intention of generating an equimolar ratio of lithiated benzene anions to unreacted phenyl bromide groups. It was observed that decreasing the amount of [NiCl2(dppp)] from 25 to 12 mg, while maintaining the ratio to bpy, did not have a substantial effect on the yield of biphenyl formed. The one-pot synthetic technique demonstrate the use of alkyllithium reagents with a catalytic amount of nickel to syntheisze coupled aryl compounds.
Pyrene dimerization into 1,1′-dipyrenyl
Nefedov
, p. 1163 - 1166 (2008/03/11)
Treatment of pyrene and some its derivatives with Cu(II) tetrafluoroborate or perchlorate in CH3CN cleanly led to the formation of 1,1′-dipyrenyls. The other polycyclic hydrocarbons (anthracene, perylene) under the same conditions provide catio
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.
1,8-Dipyrenylnaphthalenes: Syntheses, Molecular Structure, and Spectroscopic Properties
Wahl, Peter,Krieger, Claus,Schweitzer, Dieter,Staab, H. A.
, p. 260 - 276 (2007/10/02)
Syntheses of 1,8-dipyrenylnaphthalenes 1 - 3 are reported.The stereoisomers 1 and 2 were separated; their structural assignment is based on 1H NMR, on the optical activity of 2, and on X-ray structure analyses of 1 and 2.Kinetic parameters for the isomerisation 2 1 were determined by optical rotation measurements. - Emission spectra of 1 - 3 are discussed in comparison to monopyrenyl compounds 4 and 8.For 1 and 3 typical 'excimer-like' fluorescence is observed.The difference between 1 and 2 clearely demonstrates the dependence of excimer interactions between the pyrene units on the mutual orientation of the ?-systems involved. - On the basis of X-ray analyses the molecular structures of 1 - 3 are discussed with emphasis on ?...?-interactions between the pyrene units.
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.
