Perylene

Structural formula
General
Surname	Perylene
other names	peri -dinaphthylene; Dibenz [ de, kl ] anthracene;
Molecular formula	C 20 H 12
Brief description	yellow crystals
External identifiers / databases
EC number	205-900-9
ECHA InfoCard	100.005.365
PubChem	9142
Wikidata	Q417674
properties
Molar mass	252.32 g · mol -1
Physical state	firmly
Melting point	273-278 ° C
boiling point	350-400 ° C subl.
Vapor pressure	<0.1 Pa (20 ° C)
solubility	very soluble in DCM , toluene , chloroform , tetrahydrofuran , very poorly soluble in ethanol , methanol , practically insoluble in water
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Perylene is a chemical compound from the class of polycyclic aromatic hydrocarbons .

Occurrence

Perylene occurs, among other things, in coal tar and as air pollution in fine dust. The substance can also be detected in fossil crinoids and tropical termite structures. In addition, perylene is found in peat and recent sediments at the bottom of bodies of water, but also in crude oil . A possible origin from the decomposition of wood by fungi is discussed.

Manufacturing

Perylene is made by heating naphthalene with aluminum chloride or other Lewis acids . It was isolated by Roland Scholl for the first time in 1910 . Perylene can also be produced by the decarboxylation of perylenetetracarboxylic acid dianhydride (PTCDA), a widely used color pigment . This is done with the aid of microwaves in the presence of catalytic amounts of copper in the high-boiling solvent quinoline, which is often used for decarboxylation .

properties

The molecule is plane and inversely symmetric ( symmetry group D _2h ). It is a solid that forms yellow, shiny platelets and melts at 272–273 ° C. Substituted perylenes are strongly colored and resistant to heat and many chemicals . Chemical reactions for which perylene is still accessible are halogenation and Diels-Alder cycloadditions in the Bay region. Here, for example, coronas can be built up step by step with a double addition of maleic anhydride . The intermediate step after each addition of maleic anhydride consists of the decarboxylation of the thereby added acid anhydride function using copper and quinoline . Perylene is an organic semiconductor . When dissolved in dichloromethane , it fluoresces under UV light and is used as a material in organic light-emitting diodes (OLEDs).

Perylene dissolved in dichloromethane fluoresces under UV light

Perylene crystals on a glass bowl

use

Perylene is used as a pigment in the form of derivatives such as PTCDA or MePTCDI or as a pure substance in organic components such as transistors, OLEDs or organic solar cells. Other derivatives of perylene such as diindenoperylene (DIP) or dibenzo {[ f, f '] -4,4', 7,7'-tetraphenyl} diindeno [1,2,3- cd : 1 ', 2', 3 ' - lm ] perylene (DBP) and variously substituted DIPs are also used in OLEDs and organic solar cells (OSC).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Perylene data sheet (PDF) from Merck , accessed on January 18, 2011.

↑ Claudia Synowietz (Ed.): Paperback for chemists and physicists . founded by Jean d'Ans, Ellen Lax. 4th edition. Volume II: Organic Compounds . Springer, Berlin 1983, ISBN 3-540-12263-X .

↑ Grice et al .: New insights into the origin of perylene in geological samples. In: Geochimica et Cosmochimica Acta . Volume 73, Issue 21, 2009, pp. 6531–6543, doi : 10.1016 / j.gca.2009.07.029 .

↑ Liu, Huibiao et al .: Synthesis of Organic One-Dimensional Nanomaterials by Solid-Phase Reaction. In: Journal of the American Chemical Society . Volume 125, Issue 36, 2003, pp. 10794-10795, doi : 10.1021 / ja036697g .

↑ Sonia Alibert-Fouet, Isabelle Seguy et al .: Liquid-Crystalline and Electron-Deficient Coronene Oligocarboxylic Esters and Imides By Twofold Benzogenic Diels – Alder Reactions on Perylenes In: Chem. Eur. J. Volume 13, 2007, p. 1746– 1753, doi : 10.1002 / chem.200601416 .

^ Q. Chen et al .: Epitaxial Growth of a Crystalline Organic Semiconductor: Perylene / Cu {110} . In: Chemistry of Materials 14, 2002, pp. 743-749.

[merck-1] ↑ ^a ^b ^c ^d ^e ^f Perylene data sheet (PDF) from Merck , accessed on January 18, 2011.

[2] Claudia Synowietz (Ed.): Paperback for chemists and physicists . founded by Jean d'Ans, Ellen Lax. 4th edition. Volume II: Organic Compounds . Springer, Berlin 1983, ISBN 3-540-12263-X .

[3] Grice et al .: New insights into the origin of perylene in geological samples. In: Geochimica et Cosmochimica Acta . Volume 73, Issue 21, 2009, pp. 6531–6543, doi : 10.1016 / j.gca.2009.07.029 .

[4] Liu, Huibiao et al .: Synthesis of Organic One-Dimensional Nanomaterials by Solid-Phase Reaction. In: Journal of the American Chemical Society . Volume 125, Issue 36, 2003, pp. 10794-10795, doi : 10.1021 / ja036697g .

[5] Sonia Alibert-Fouet, Isabelle Seguy et al .: Liquid-Crystalline and Electron-Deficient Coronene Oligocarboxylic Esters and Imides By Twofold Benzogenic Diels – Alder Reactions on Perylenes In: Chem. Eur. J. Volume 13, 2007, p. 1746– 1753, doi : 10.1002 / chem.200601416 .

[6] Q. Chen et al .: Epitaxial Growth of a Crystalline Organic Semiconductor: Perylene / Cu {110} . In: Chemistry of Materials 14, 2002, pp. 743-749.