Perylenetetracarboxylic dianhydride

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Perylenetetracarboxylic dianhydride
Skeletal formula of PTCDA
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
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/cm3
Melting point ~350 °C[1]
Structure
Monoclinic
, P21/c
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Perylenetetracarboxylic dianhydride (PTCDA) is an

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]

Structure

PTCDA consists of a

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]
scanning tunneling microscopy image.[5]

Use

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

References

Wikimedia Commons has media related to PTCDA.
  1. ^ PTCDA.
  2. ISSN 0743-7463
    .
  3. doi:10.1016/0022-0248(92)90658-6
    .
  4. PMID 26178193
    .
  5. PMID 26440933
    .
  6. doi:10.1002/14356007.a20_371
  7. doi:10.1002/9783527626915.ch16
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