Perylenetetracarboxylic dianhydride

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 and dyes. It is a dark red solid with low solubility in aromatic solvents. The compound has attracted much interest as an organic semiconductor.^[2]

Perylenetetracarboxylic dianhydride

Names
Preferred IUPAC name Peryleno[3,4-cd:9,11-c′d′]dipyran-3,5,10,12-tetrone
Other names Perylene-3,4,9,10-tetracarboxylic dianhydride, Pigment Red 224
Identifiers
CAS Number	128-69-8
3D model (JSmol)	Interactive image
ChemSpider	60534
ECHA InfoCard	100.004.461
EC Number	204-905-3
PubChem CID	67191
UNII	NH27FW2PET Y
CompTox Dashboard (EPA)	DTXSID1059577
InChI InChI=1S/C24H8O6/c25-21-13-5-1-9-10-2-6-15-20-16(24(28)30-23(15)27)8-4-12(18(10)20)11-3-7-14(22(26)29-21)19(13)17(9)11/h1-8H Key: CLYVDMAATCIVBF-UHFFFAOYSA-N InChI=1/C24H8O6/c25-21-13-5-1-9-10-2-6-15-20-16(24(28)30-23(15)27)8-4-12(18(10)20)11-3-7-14(22(26)29-21)19(13)17(9)11/h1-8H Key: CLYVDMAATCIVBF-UHFFFAOYAS
SMILES c1cc2c3c(ccc4c3c1c5ccc6c7c5c4ccc7C(=O)OC6=O)C(=O)OC2=O
Properties
Chemical formula	C24H8O6
Molar mass	392.32
Density	1.7 g/cm3
Melting point	~350 °C[1]
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

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.^[3] 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°

Self-assembly and films

Atomic force microscopy image of a single PTCDA molecule on Si at room temperature.^[4]

Self-assembly of PTCDA molecules on NaCl, scanning tunneling microscopy image.^[5]

Use

The main industrial use of PTCDA is as a precursor to Rylene dyes.^[6][7]

References

1. PTCDA.
2. Russell, James C.; Blunt, Matthew O.; Goretzki, Gudrun; Phillips, Anna G.; Champness, Neil R.; Beton, Peter H. (2010). "Solubilized Derivatives of Perylenetetracarboxylic Dianhydride (PTCDA) Adsorbed on Highly Oriented Pyrolytic Graphite". Langmuir. 26 (6): 3972–3974. doi:10.1021/la903335v. ISSN 0743-7463.
3. Möbus, M. & Karl, N. (1992). "Structure of perylene-tetracarboxylic-dianhydride thin films on alkali halide crystal substrates". Journal of Crystal Growth. 116 (3–4): 495–504. doi:10.1016/0022-0248(92)90658-6.
4. Iwata, Kota; Yamazaki, Shiro; Mutombo, Pingo; Hapala, Prokop; Ondráček, Martin; Jelínek, Pavel; Sugimoto, Yoshiaki (2015). "Chemical structure imaging of a single molecule by atomic force microscopy at room temperature". Nature Communications. 6: 7766. doi:10.1038/ncomms8766. PMC 4518281. PMID 26178193.
5. Cochrane, K. A.; Schiffrin, A.; Roussy, T. S.; Capsoni, M.; Burke, S. A. (2015). "Pronounced polarization-induced energy level shifts at boundaries of organic semiconductor nanostructures". Nature Communications. 6: 8312. doi:10.1038/ncomms9312. PMC 4600718. PMID 26440933.
6. Hunger, K. and Herbst, W. (2012) "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi:10.1002/14356007.a20_371
7. Greene, M. (2009) "Perylene Pigments", pp. 261–274 in High Performance Pigments, Wiley-VCH, Weinheim.doi:10.1002/9783527626915.ch16