Perylenetetracarboxylic dianhydride
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |
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| 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) |
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| ChemSpider | |
| ECHA InfoCard | 100.004.461 |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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).
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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
Use
The main industrial use of PTCDA is as a precursor to Rylene dyes.[6][7]
