198-55-0

Usage

Uses

1. Used in Photochemistry:
Perylene is used as an acceptor for pristine C70, which serves as a sensitizer for efficient triplet-triplet annihilation upconversion. This application has demonstrated improved stability under continuous laser irradiation compared to the benchmark Pt(II)-octaethylporphyrin.
2. Used in Optoelectronics:
Perylene is used as a dopant representing a blue fluorescent dye on a white-emitting polymer film. This application takes advantage of its fluorescent properties to enhance the performance of optoelectronic devices.
3. Used in Dyes and Metabolites:
Perylene's fluorescent nature also makes it useful in the development of dyes and metabolites, where its unique properties can be harnessed for various purposes, such as imaging or sensing.
4. Used in Surface Science:
The structure and properties of perylene dye layers adsorbed on the surface of Ru (0001) have been investigated using ultraviolet photoemission spectroscopy and low energy electron diffraction. This application contributes to the understanding of perylene's behavior and interactions at the molecular level, which can be beneficial for further development and optimization of its use in various industries.

Safety Profile

Questionable carcinogen. Mutation data reported. Whenheated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Purify perylene by silica-gel chromatography of its recrystallised picrate. [Ware J Am Chem Soc 83 4374 1961.] Crystallise it from *benzene, toluene or EtOH and sublime it at 142o in a flow of oxygen-free nitrogen. It forms a 1:1 *benzene-complex (m 223-224.5o needles from *C6H6), and a 1:2 *benzene-complex (m 154-155o from *C6H6 or H2O). The 2,4,7-trinitrofluoren-9-one has m 270-271o (from EtOH/*C6H6). [Gorman et al. J Am Chem Soc 107 4404 1985, Johansson et al. J Am Chem Soc 109 7374 1987, Beilstein 5 III 2521, 5 IV 2689.]

InChI:InChI=1/C20H12/c1-5-13-6-2-11-17-18-12-4-8-14-7-3-10-16(20(14)18)15(9-1)19(13)17/h1-12H

Upstream product

• 1730-04-7 1,8-diiodonaphthalene 
• 612-78-2 2,2'-binaphthalene 
• 16306-20-0 1,2,7,8-tetrahydro-perylene-3,9-dione 
• 99100-67-1 perylene-1,12-diol 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 81-32-3 perylene-3,4,9,10-tetracarboxylic acid 
• 60-29-7 diethyl ether 
• 604-53-5 1,1'-bisnaphthalene 
• 591-51-5 phenyllithium 
• 13190-50-6 4-dimethylaminophenyllithium 
• 135-19-3 β-naphthol 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 630-17-1 2,2-dimethylpropyl bromide 
• 5335-87-5 4,4'-dimethoxyphenyl disulfide 

Downstream Products

• 188-72-7 terrylene 
• 128-64-3 isoviolanthrone 
• 26556-97-8 3,9-dibenzoyl-perylene 
• 31593-94-9 3,4-dibenzoyl-perylene 
• 856340-82-4 3,4-bis-(4-chloro-benzoyl)-perylene 
• 856340-91-5 3,9-bis-(4-methoxy-benzoyl)-perylene 
• 75626-96-9 3,9-di-o-toluoyl-perylene 
• 15251-37-3 perylene; compound with 1,3,5-trinitro-benzene 
• 80663-92-9 2,5,8,11-tetra-tert-butylperylene 
• 10350-33-1 1-Methylperylene 
• 20589-63-3 3-Nitroperylene 
• 35337-20-3 1-nitroperilene 
• 85514-20-1 3,10-Dibromoperylene 
• 56752-35-3 3,9-dibromoperylene 

Related news

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Two donor-σ-acceptor-σ-donor triads incorporating tetrathiafulvalene (TTF) and 3,4,9,10-perylene tetracarboxylic diimides (PDI) units were synthesized. The structures of the triads and their intermediates were characterized by 1 H NMR, 13 C NMR, MS, IR. The results of UV–vis a...detailed

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Novel bispinacolborane‐N,N′‐bis(octyl)‐3,4,9,10‐perylenetetracarboxylic acid bisimide (PBI) was synthesized in high yield. The title compound is a key intermediate in the preparation of PBI aryl derivatives through Suzuki cross‐coupling by using a large variety of easily accessible aryl ha...detailed

Relevant academic research and scientific papers

Electronic spectra of radical cations and their correlation with photoelectron spectra-III. Perylenes and coronenes

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.

Electron Transfer from CO2.- to Perylene in Cyclohexane

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.

Temperature Coefficients of Half-wave Potentials and Entropies of Transfer of Cations in Aprotic Solvents

Temperature coefficients of polarographic half-wave potentials for Li+, Na+, K+, Rb+, Cs+, Tl+, Cu2+, Zn2+, Cd2+, Ba2+, Pb2+, bis(biphenyl)chromium(I) tetraphenylborate, ferrocene and perylene have been derived from measurements vs.Ag/Ag+ (0.01 mol dm-3) electrodes kept at 25 deg C in 0.1 mol dm-3 solutions of tetrabutylammonium perchlorate in dimethyl sulphoxide, N,N-dimethylformamide, hexamethylphosphoric triamide and propylene carbonate.Entropies for the above mentioned redox couples and for Ag+ were calculated for reversible electrode reactions on the basis of the assumption of a negligible thermal diffusion potential.This assumption was also employed to calculate single-ion entropies of transfer from N,N-dimethylformamide into dimethyl sulphoxide, propylene carbonate and hexamethylphosphoric triamide.

Transient absorption spectroscopy of high-mobility ions in decalin

Transient absorption spectroscopy is used to demonstrate that pulse radiolysis of a decalin mixture (63% cis-decalin + 37% trans-decalin) with 15 MeV electrons results in formation of high-mobility solvent holes. These radical cations react with perylene with a rate constant of 8.5 × 1010 mol-1 dm3 s-1. This scavenging is faster by an order of magnitude than ion-molecule reactions of normally diffusing ions (～(5-7.5) × 109 mol-1 dm3 s-1). Under conditions of the experiment, the lifetime of the rapidly migrating solvent holes is ～150 ns, which identifies them as the high-mobility cations observed by dc and microwave conductivity.

Photoinduced Electron-Transfer Reactions of Perylene in Acetonitrile

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.

peri-Naphthylenediamines 24.* Double 1,1′-binaphthalene "proton sponge"

4,5,4′,5′-Tetrakis(dimethylamino)-1,1′-binaphthalene, unknown previously, was obtained in -20% yield by the oxidation of 1,8-bis(dimethylamino)naphthalene with Tl(OAc)3 or Pb(OAc)4 at low temperatures. Treatment of the reaction produ

Mechanism of the Formation of Transient Aromatic Radical Cations in Alcohols: Laser Flash Photolysis and Pulse Radiolysis Studies

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.

Flash vacuum thermolysis of acenaphtho[1,2-a]acenaphthylene. Thermal behaviour of a polycyclic aromatic hydrocarbon containing two abutting pentagons

FVT of acenaphtho[1,2-a]acenaphthylene (1) gave acenaphtho[1,2- elacenaphthylene (2). cyclopenta[cd]perylene (3) and cyclopenia[rst]benzo[hi]chrysene (4). The formation of 3 and 4 indicates that, besides ring contraction/ring expansion of 1 giving 2, homolytic scission of a five-membered ring carbon-carbon single bond of 1 is an important competitive process.

Colloid chemical reaction route to the preparation of nearly monodispersed perylene nanoparticles: Size-tunable synthesis and three-dimensional self-organization

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.

Light-Induced Charge Separation by Formation of Insoluble Precipitates

Preliminary experiments are reported on light-induced charge separation by quenching electronically excited species with formation of insoluble precipitates.Irradiation of acceptor-donor mixtures of 3-dimethylaminoperylene metaphosphate/tetramethyl-p-phenylenediamine (TMPD) and of Ag+/perylene, respectively, in methylene chloride and with tetrabutylammonium perchlorate as supporing electrolyte formed precipitates of TMPD+ClO4- and Ag, respectively.The precipitates were separated from the solution by a platinum filter in a flow cell, which served as a simple battery for conversion of stored chemical energy into electrical energy.The quantum yield was about 1E-6 and the battery voltage about 60 mV.