198-55-0Relevant articles and documents
Electronic spectra of radical cations and their correlation with photoelectron spectra-III. Perylenes and coronenes
Khan, Zahid H.
, p. 313 - 320 (1988)
Radical cations of perylene, 1,12-benzoperylene, coronene, 1,2-benzocoronene, and naphtho-(2',3':1,2)coronene are produced by photooxidation in boric acid matrix and their electronic absorption spectra are measured.The results are discussed in terms of Longuet-Higgins-Pople and Wasilewski type Open-Shell SCF-MO calculations and the u.v. photoelectron spectra of the parent molecules.The correspondence between optical and photoelectron spectra is found to be fairly good.A correlation diagram for the electronic transitions for some of the molecular ions is presented to demonstrate their movement from one system to another.Finally, an express ion showing the relationship between the first ionization potentials of the parent molecules and A-type electronic band energies in the cation spectra is given from which the first IP's of the hydocarbons may be estimated.
Metal Hydride Reduction via Single Electron Transfer. 2. Evidence for an Electron-Transfer Pathway in the Reactions of Simple and Complex Metal Hydrides of the Main Group Metals with Polynuclear Hydrocarbons
Ashby, E. C.,Goel, A. B.,DePriest, R. N.,Prasad, H. S.
, p. 973 - 975 (1981)
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Electron Transfer from CO2.- to Perylene in Cyclohexane
Sauer, Myran C.,Jonah, Charles D.
, p. 5872 - 5875 (1992)
CO2.- formed by the reaction of the electron with CO2 in cyclohexane transfers an electron to perylene with a rate constant of 2.9 * 1010 M-1 s-1.Gε580nm for the perylene radical anion is 9 * 103 molecules (100 eV)-1 M-1 cm-1.The transfer of an electron from CO2.- to an aromatic molecule is a significant process when CO2 is used as an electron scavenger in solutions where the production of excited states of the aromatic molecule is studied.
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Hansgirg,Zinke
, p. 403 (1919)
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Iwashima,Aoki
, p. 2789 (1968)
Photoinduced Electron-Transfer Reactions of Perylene in Acetonitrile
Vauthey, Eric,Suppan, Paul,Haselbach, Edwin,Davidson, Robert Stephen
, p. 430 - 437 (1986)
Laser-flash-photolysis experiments show that, in MeCN at 20 deg, perylene (P) undergoes three distinct electron-transfer reactions: a) 1P* + MeCN -> P.+ + MeCN.- b) 1P* + P -> P.+ + P.- c) 3P* + 3P* -> (P x P)* -> P.+ + P.-.These processes originate probably from the thermally relaxed excited states of P.
Mechanism of the Formation of Transient Aromatic Radical Cations in Alcohols: Laser Flash Photolysis and Pulse Radiolysis Studies
Liu, A.-D.,Sauer, M. C.,Jonah, C. D.,Trifunac, A. D.
, p. 9293 - 9298 (1992)
A product of the reaction of SF6 with a solvated electron in an alcohol (presumably SF5.) reacts with an aromatic solute molecule such as anthracene, perylene, naphthalene, or hexamethylbenzene to form aromatic radical cations.This reaction depends on both the ionization potential of the aromatic solute molecule and the polarity of the solvent.The rates of these reactions are (except for naphthalene) in the range of (1-10) * 109 M-1 s-1.The reaction of the aromatic molecule (except for naphthalene) with SF5. appears to have two pathways, one of which leads to the radical cation and a second that forms an undetermined product.
Colloid chemical reaction route to the preparation of nearly monodispersed perylene nanoparticles: Size-tunable synthesis and three-dimensional self-organization
Kang, Longtian,Wang, Zhechen,Cao, Zongwei,Ma, Ying,Fu, Hongbing,Yao, Jiannian
, p. 7305 - 7312 (2007)
By employing a colloid chemical reaction method we demonstrate the preparation of organic nanoparticles composed of perylene molecules (PeNPs) based on the reduction of perylene perchlorate by Br- anions in the presence of cetyl trimethyl ammonium bromide (CTA+Br-) in acetonitrile. A discrete nucleation event, followed by a slower controlled growth on the existing particles, is identified during formation of PeNPs. By changing the growth parameters, such as the monomer concentration and the method of injection, quasi-spherical PeNPs with controllable sizes from 25 to 90 nm could be obtained. The homogeneous solution phase of this method makes it capable of large-scale synthesis of PeNPs with a size distribution (+ around the PeNPs. The three-dimensional, hierarchical self-organization of 25-nm PeNPs building blocks is observed to form nanobelts and square nanorods, possibly templated by the CTA+ lamellar micelle structures in acetonitrile. Spectroscopic results reveal two kinds of trends in the development of the optical properties of perylene as they evolve from the molecular to the bulk phase in the nanometer range. The so-called size dependence is evidenced by a switch from Y-type to E-type excimers as the size of the PeNPs increased from 25 to 90 nm. As the 25-nm PeNPs organize into nanobelts or square nanorods the oscillator strength of the Y-type excimers is relatively enhanced. That is, collective phenomena develop as the proximal particles interact in the glassy solids. Our very recent results indicate that this colloid chemical reaction method can also be applied to other organic compounds.
Evidence for Single Electron Transfer in the Reactions of Alkali Metal Amides and Alkoxides with Alkyl Halides and Polynuclear Hydrocarbons
Ashby, E. C.,Goel, A. B.,DePriest, R. N.
, p. 2429 - 2431 (1981)
Evidence for single electron transfer as the major pathway in reactions previously considered to be classic SN1 and SN2 pathways has been obtained.In this connection, the reaction of KOBu-t with trityl bromide has been shown to proceed through the trityl radical, and the reaction of LiN(i-Pr)2 with a primary alkyl iodide probe gave evidence of proceeding by single electron transfer, as indicated by the cyclized nature of the product as a result of a radical intermediate.
Arenium cation or radical cation? An insight into the cyclodehydrogenation reaction of 2-substituted binaphthyls mediated by Lewis acids
Baumgartner, María T.,Camargo Solórzano, Patricia,Jimenez, Liliana B.,Puiatti, Marcelo
, p. 21974 - 21985 (2020/07/03)
Perylene and its derivatives are some of the most interesting chromophores in the field of molecular design. One of the most employed methodologies for their synthesis is the cyclodehydrogenation of binaphthyls mediated by Lewis acids. In this article, we investigated the cyclodehydrogenation reaction of 2-substituted binaphthyls to afford thebay-substituted perylene. By using AlCl3as a Lewis acid and high temperatures (the Scholl reaction), two new products bearing NH2and N(CH3)2groups at position 2 of the perylene ring were synthesized. Under these conditions, we were also able to obtain terrylene from ternaphthalene in 38percent yield after two cyclodehydrogenation reactions in a single step. The attempts to promote the formation of a radical cation (necessary intermediary for the oxidative aromatic coupling mechanism) by using FeCl3or a strong oxidant like 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) did not yield the expected products. DFT calculations suggested that the lack of reaction for oxidative aromatic coupling is caused by the difference between the oxidation potentials of the donor/acceptor couple. In the case of the Scholl reaction, the regiochemistry involved in the formation of the σ-complex together with the activation energy of the C-C coupling reaction helped to explain the differences in the reactivity of the different substrates studied.
Scholl Cyclizations of Aryl Naphthalenes: Rearrangement Precedes Cyclization
Skraba-Joiner, Sarah L.,McLaughlin, Erin C.,Ajaz, Aida,Thamatam, Rajesh,Johnson, Richard P.
, p. 9578 - 9583 (2015/10/12)
In 1910, Scholl, Seer, and Weitzenbock reported the AlCl3-catalyzed cyclization of 1,1′-binaphthyl to perylene. We provide evidence that this classic organic name reaction proceeds through sequential and reversible formation of 1,2′- and 2,2′-binaphthyl isomers. Acid-catalyzed isomerization of 1,1′-binaphthyl to 2,2′-binaphthyl has been noted previously. The superacid trifluoromethanesulfonic acid (TfOH), 1 M in dichloroethane, catalyzes these rearrangements, with slower cyclization to perylene. Minor cyclization products are benzo[k]fluoranthene and benzo[j]fluoranthene. At ambient temperature, the observed equilibrium ratio of 1,1′-binaphthyl, 1,2′-binaphthyl, and 2,2′-binaphthyl is 1:3:97. DFT calculations with the inclusion of solvation support a mechanistic scheme in which ipso-arenium ions are responsible for rearrangements; however, we cannot distinguish between arenium ion and radical cation mechanisms for the cyclization steps. Under similar reaction conditions, 1-phenylnaphthalene interconverts with 2-phenylnaphthalene, with the latter favored at equilibrium (5:95 ratio), and also converts slowly to fluoranthene. Computations again support an arenium ion mechanism for rearrangements.
SEPARATION OF NANOPARTICLES
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Page/Page column, (2013/11/19)
This invention is directed to separation, optimization and purification of nano-materials using self-assembled perylene diimide membranes, wherein said perylene diimide membrane is recyclable.
