Perylene

• Peri- Dinaphthylen
• Anthracene dibenz [ de, kl]

Yellow crystals

Fixed

273-278 ° C

350-400 ° C subl.

< 0.1 Pa ( 20 ° C)

Very soluble in DCM, toluene, chloroform, tetrahydrofuran, very slightly soluble in ethanol, methanol, practically insoluble in water

Template: Infobox chemical / molecular formula search available

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

Occurrence

Perylene is for example found in coal tar and as air pollution particulate matter. Also in fossil crinoids and tropical termite, the substance can be detected. In addition, perylene is found in peat and recent sediments at the bottom of water bodies, but also in crude oil. A possible origin of the degradation of wood by fungi is discussed.

Production

Perylene is formed by heating naphthalene with aluminum chloride or other Lewis acids. It was first isolated in 1910 by Roland Scholl. Perylene can also be prepared by decarboxylation of perylene tetracarboxylic ( 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 and decarboxylation commonly used quinoline.

Properties

The molecule is planar and inversion symmetry ( symmetry group D2h ). It is a solid that forms yellow shining plates and melts at 272-273 ° C. Substituted Perylene are strongly colored and resistant to heat and many chemicals. Chemical reactions that perylene is still accessible, for example, halogenation and Diels- Alder cycloadditions in the Bay Area. This can be established, for example, with a two-time step by step addition of maleic anhydride coronene. The intermediate step after each addition of maleic anhydride from the decarboxylation of the acid anhydride attached by using copper and quinoline. Perylene is an organic semiconductor. Dissolved in dichloromethane it fluoresces under ultraviolet light and wherein the organic light emitting diode ( OLED) is used as the material.

Use

Perylene is used in the form of derivatives such as PTCDA or MePTCDI as a pigment or as these impurities in organic devices such as transistors, OLED or organic solar cells. Further derivatives of perylene such as Diindenoperylen (DIP) or dibenzo { [f, f ' ] -4,4', 7,7 ' - tetraphenyl } diindeno [ 1,2,3- cd: 1', 2 ', 3' -lm ] perylene (DBP ) and various substituted DIPs also find application in OLEDs and organic solar cells ( OSC).