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Perylenetetracarboxylic dianhydride
Skeletal formula of PTCDA
Names
Preferred IUPAC name
Peryleno※dipyran-3,5,10,12-tetrone
Other names
Perylene-3,4,9,10-tetracarboxylic dianhydride, Pigment Red 224
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.461 Edit this at Wikidata
EC Number
  • 204-905-3
UNII
  • 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
  • c1cc2c3c(ccc4c3c1c5ccc6c7c5c4ccc7C(=O)OC6=O)C(=O)OC2=O
Properties
C24H8O6
Molar mass 392.32
Density 1.7 g/cm
Melting point ~350 °C
Structure
Monoclinic, P21/c
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C ※, 100 kPa).
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 Îł
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.
Self-assembly of PTCDA molecules on NaCl, scanning tunneling microscopy image.

Use※

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

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; JelĂ­nek, 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
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