Perylene

Base Information

• Chemical Name: Perylene
• CAS No.: 198-55-0
• Deprecated CAS: 77392-71-3,733006-66-1,733006-66-1
• Molecular Formula: C20H12
• Molecular Weight: 252.315
• Hs Code.: 29029080
• European Community (EC) Number: 205-900-9
• NSC Number: 6512
• UNII: 5QD5427UN7
• DSSTox Substance ID: DTXSID4047753
• Nikkaji Number: J2.972F
• Wikipedia: Perylene
• Wikidata: Q417674
• Metabolomics Workbench ID: 54111
• ChEMBL ID: CHEMBL4296691
• Mol file: 198-55-0.mol

Synonyms:Peri Dinaphthalene;Peri-Dinaphthalene;Perilene;Perylene

Chemical Property of Perylene

Chemical Property:

• Appearance/Colour: brown solid
• Vapor Pressure: 1.81E-08mmHg at 25°C
• Melting Point: 276-279 °C(lit.)
• Refractive Index: 1.887
• Boiling Point: 467.5 °C at 760 mmHg
• Flash Point: 228.6 °C
• PSA: 0.00000
• Density: 1.286 g/cm³
• LogP: 5.73720
• Storage Temp.: 2-8°C
• Solubility.: <0.0001g/l
• Water Solubility.: INSOLUBLE
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 252.093900383
• Heavy Atom Count: 20
• Complexity: 304

Purity/Quality:

99% ^*data from raw suppliers

Perylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T
• Hazard Codes: Xn,T,N
• Statements: 40-63-43-36/37/38-23/24/25-45-67-50/53
• Safety Statements: 22-24/25-45-36/37-23-53-61-60

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC2=C3C(=C1)C4=CC=CC5=C4C(=CC=C5)C3=CC=C2
• Uses: Perylene has been used as an acceptor for pristine C70 to be used as a sensitizer for efficient triplet-triplet annihilation upconversion; which has shown improved stability under continuous laser irradiation compared to the benchmark Pt(II)-ocetaethylprphyrin. Perylene has also been used as a dopant representing blue fluorescent dye on a white-emitting polymer film. Dyes and metabolites.

Technology Process of Perylene

There total 154 articles about Perylene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.5%

2,5-di-tert-butylaniline (21860-03-7) + perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → PERYLENE (198-55-0) + N,N'-bis(2,5-di-tert-butylphenyl)perylene-3,4:9,10-bis(dicarboximide) (83054-80-2,99571-55-8,99571-56-9,121468-40-4,121470-76-6) + N-(2,5-di-tert-butylphenyl)-perylene-3,4-dicarboxylic imide (165261-25-6)

Guidance literature:

With 1H-imidazole; zinc diacetate; water; at 190 ℃; for 23h;

Reference yield: 34.0%

1,1'-binaphthyl-4,4',5,5',8,8'-hexacarboxylic acid (49610-16-4) → naphthalene (91-20-3,71998-51-1,72931-45-4) + PERYLENE (198-55-0)

Guidance literature:

With sodalime; at 450 - 500 ℃; Yields of byproduct given; stream of superheated steam;

Reference yield: 29.0%

naphthalene (91-20-3,71998-51-1,72931-45-4) → 1,1'-bisnaphthalene (604-53-5) + 1-(naphthalen-2-yl)naphthalene (4325-74-0) + 2,2'-binaphthalene (612-78-2) + PERYLENE (198-55-0)

Guidance literature:

With iron(III) perchlorate; In acetonitrile; at 28 ℃; for 2h;

upstream raw materials:

1,8-diiodonaphthalene

2,2'-binaphthalene

perylene-3,10-dione

1,2,7,8-tetrahydro-perylene-3,9-dione

Downstream raw materials:

3,4-bis-(4-chloro-benzoyl)-perylene

3,9-bis-(4-methoxy-benzoyl)-perylene

3,9-di-o-toluoyl-perylene

n-butyl radical

Refernces

• 1、 Lohmann. "-". . . Retrieved 1972.
• 2、 Zinke,Stimler,Reuss. "-". . p. 415,421. Retrieved 1934.
• 3、 Gritzner, Gerhard,Lewandowski, Andrzej. "Temperature Coefficients of Half-wave Potentials and Entropies of Transfer of Cations in Aprotic Solvents". . p. 2599 - 2602. Retrieved 1991.
• 4、 Shkrob,Sauer Jr.,Yan,Trifunac. "Transient absorption spectroscopy of high-mobility ions in decalin". . p. 6876 - 6878. Retrieved 1996.
• 5、 Posstowsski,Bednjagina. "-". . . Retrieved 1938.
• 6、 Vistorobskii,Pozharskii,Rudnev. "peri-Naphthylenediamines 24.* Double 1,1′-binaphthalene "proton sponge"". . p. 91 - 96. Retrieved 1998.
• 7、 Sarobe, Martin,Kwint, Huibert C.,Fleer, Theun,Jenneskens, Leonardus W.,Wesseling, Jolanda. "Flash vacuum thermolysis of acenaphtho[1,2-a]acenaphthylene. Thermal behaviour of a polycyclic aromatic hydrocarbon containing two abutting pentagons". . p. 9823 - 9826. Retrieved 1998.
• 8、 Grabner, Erich Walter,Hessberger, Harald. "Light-Induced Charge Separation by Formation of Insoluble Precipitates". . p. 226 - 230. Retrieved 1987.
• 9、 Rickhaus, Michel,Belanger, Anthony P.,Wegner, Hermann A.,Scott, Lawrence T.. "An oxidation induced by potassium metal. Studies on the anionic cyclodehydrogenation of 1,1′-binaphthyl to perylene". . p. 7358 - 7364. Retrieved 2010.
• 10、 Wu, Huang,Chen, Yong,Zhang, Long,Anamimoghadam, Ommid,Shen, Dengke,Liu, Zhichang,Cai, Kang,Pezzato, Cristian,Stern, Charlotte L.,Liu, Yu,Stoddart, J. Fraser. "A Dynamic Tetracationic Macrocycle Exhibiting Photoswitchable Molecular Encapsulation". supporting information. p. 1280 - 1289. Retrieved 2019/01/14.