Perylenetetracarboxylic dianhydride

Perylenetetracarboxylic dianhydride
Names


Preferred IUPAC name Perylenodipyran-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
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/h1-8HKey: 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/h1-8HKey: CLYVDMAATCIVBF-UHFFFAOYAS
SMILES c1cc2c3c(ccc4c3c1c5ccc6c7c5c4ccc7C(=O)OC6=O)C(=O)OC2=O
Properties
Chemical formula	C₂₄H₈O₆
Molar mass	392.32
Density	1.7 g/cm
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 , 100 kPa). Infobox references

Chemical compound

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.

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/cm, 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

Use

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

References

PTCDA.
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.
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.
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.
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.
Hunger, K. and Herbst, W. (2012) "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi:10.1002/14356007.a20_371
Greene, M. (2009) "Perylene Pigments", pp. 261–274 in High Performance Pigments, Wiley-VCH, Weinheim.doi:10.1002/9783527626915.ch16

v t e Vat dyes
Blue	4 36
Green	1 9
Orange	1 3
Red	23 29
Yellow	1 4

v t e Dyeing
Techniques	Batik Dyeing Ikat Kasuri Kalamkari Katazome Leheria Mordant Reactive dye printing Resist Ring dyeing Rōketsuzome Shibori Tie-dye Tsutsugaki Yūzen
Types of dyes	Dyes Natural Acid Reactive Solvent Substantive Sulfur Vat Disperse Discharge Pigment
Traditional textile dyes	Armenian cochineal Black walnut Bloodroot Brazilin Cochineal Cudbear Cutch Dyewoods Fustic Gamboge Dyer's broom Henna Indigo Kermes Logwood Madder Polish cochineal Saffron Turmeric Tyrian purple Weld Woad
History	Use of saffron Traditional dyes of the Scottish Highlands
Craft dyes	Dylon Inkodye Procion Rit
Reference	Glossary of dyeing terms List of dyes

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