Perylenetetracarboxylic dianhydride (PTCDA) is an

organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...

dye molecule and an

organic semiconductor Organic semiconductors are solids whose building blocks are pi-bonded molecules or polymers made up by carbon and hydrogen atoms and – at times – heteroatoms such as nitrogen, sulfur and oxygen. They exist in the form of molecular crystals o ...

. It is used as a precursor to a class of molecules known as

Rylene dye A rylene dye is a dye based on the rylene framework of naphthalene units linked in peri-positions. In homologues additional naphthalene units are added, forming compounds — or ''poly(peri-naphthalene)s'' — such as perylene, terrylene and quart ...

s, which are useful as

pigments A pigment is a powder used to add or alter color or change visual appearance. Pigments are completely or nearly solubility, insoluble and reactivity (chemistry), chemically unreactive in water or another medium; in contrast, dyes are colored sub ...

and

dye Juan de Guillebon, better known by his stage name DyE, is a French musician. He is known for the music video of the single "Fantasy Fantasy is a genre of speculative fiction that involves supernatural or Magic (supernatural), magical ele ...

s. It is a dark red solid with low solubility in aromatic solvents. The compound has attracted much interest as an organic semiconductor.

Structure

PTCDA consists of a

perylene Perylene or perilene is a polycyclic aromatic hydrocarbon with the chemical formula C20H12, occurring as a brown solid. It or its derivatives may be carcinogenic, and it is considered to be a hazardous pollutant. In cell membrane cytochemistry, ...

core to which two

anhydride An acid anhydride is a type of chemical compound derived by the removal of water molecules from an acid (chemistry), acid. In organic chemistry, organic acid anhydrides contain the functional group . Organic acid anhydrides often form when one ...

groups have been attached, one at either side. It occurs in two crystalline forms, α and β. Both have the P2₁/c

monoclinic In crystallography, the monoclinic crystal system is one of the seven crystal systems. A crystal system is described by three Vector (geometric), vectors. In the monoclinic system, the crystal is described by vectors of unequal lengths, as in t ...

symmetry and a density of ca. 1.7 g/cm³, which is relatively high for organic compounds. Their lattice parameters are:

Self-assembly and films

Use

The main industrial use of PTCDA is as a precursor to

s.Hunger, K. and Herbst, W. (2012) "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim. Greene, M. (2009) "Perylene Pigments", pp. 261–274 in High Performance Pigments, Wiley-VCH, Weinheim.

References

{{dyeing Perylene dyes Vat dyes Organic semiconductors