Perylenetetracarboxylic dianhydride

Perylenetetracarboxylic dianhydride

Names
Other names Perylene-3,4,9,10-tetracarboxylic dianhydride, Pigment Red 224
Identifiers
CAS Number	128-69-8
ECHA InfoCard	100.004.461
CompTox Dashboard (EPA)	DTXSID1059577
Properties
Chemical formula	C24H8O6
Molar mass	392.32
Density	1.7 g/cm3
Melting point	~350 °C
Structure
Crystal structure	Monoclinic, P21/c
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Perylenetetracarboxylic dianhydride (PTCDA) is an organic dye molecule and an organic semiconductor. It is used as a precursor to a class of molecules known as Rylene dyes, which are useful as pigments, dyes and organic semiconductors.

Structure

PTCDA consists of a perylene core to which two anhydride groups have been attached, one at either side. It occurs in two crystalline forms, α and β. Both have the P2₁/c monoclinic symmetry and a density of ca. 1.7 g/cm³, which is relatively high for organic compounds. Their lattice parameters are:

Form	a	b	c	γ
α	0.374 nm	1.196 nm	1.734 nm	98.8°
β	0.378 nm	1.930 nm	1.077 nm	83.6°

Uses

Atomic force microscopy image of a single PTCDA molecule on Si at room temperature.

Self-assembly of PTCDA molecules on NaCl, scanning tunneling microscopy image.

As a chemical precursor

The main industrial use of PTCDA is as a precursor to Rylene dyes.

As an organic semiconductor

PTCDA's relatively simple chemical structure makes it attractive as a model compound for the study of organic semiconductors. It has among others been used to create single-crystal OFETs and organic solar cells. It is also often used in the study of the interaction between organic semiconductors and the surfaces of metals, insulators and inorganic semiconductors. The application of PTCDA as an organic semiconductor is limited by it's low solubility in common solvents, which makes it unattractive for most industrial applications.