Perylenetetracarboxylic dianhydride
{{Chembox
| ImageFile = Perylenetetracarboxylic dianhydride.png
| ImageSize = 220
| ImageAlt = Skeletal formula of PTCDA
| ImageFile1 = PeryleneDianhydSample.JPG
| ImageSize1 = 220
| PIN = Peryleno[3,4-cd:9,11-c′d′]dipyran-3,5,10,12-tetrone
| OtherNames = Perylene-3,4,9,10-tetracarboxylic dianhydride, Pigment Red 224
|Section1={{Chembox Identifiers
| CASNo = 128-69-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = NH27FW2PET
| EINECS = 204-905-3
| PubChem = 67191
| ChemSpiderID = 60534
| SMILES = c1cc2c3c(ccc4c3c1c5ccc6c7c5c4ccc7C(=O)OC6=O)C(=O)OC2=O
| 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
| InChIKey = CLYVDMAATCIVBF-UHFFFAOYAS
| StdInChI = 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
| StdInChIKey = CLYVDMAATCIVBF-UHFFFAOYSA-N }}
|Section2={{Chembox Properties
| Formula = C24H8O6
| MolarMass = 392.32
| Appearance =
| Density = 1.7 g/cm3
| MeltingPt = ~350 °C[http://123.56.90.132/en/chem/PTCDA PTCDA].
| BoilingPt =
| Solubility = }}
| Section3 = {{Chembox Structure
| CrystalStruct = Monoclinic, P21/c
| MolShape =
}}
|Section7={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
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.{{cite journal|last1=Russell|first1=James C.|last2=Blunt|first2=Matthew O.|last3=Goretzki|first3=Gudrun|last4=Phillips|first4=Anna G.|last5=Champness|first5=Neil R.|last6=Beton|first6=Peter H.|title=Solubilized Derivatives of Perylenetetracarboxylic Dianhydride (PTCDA) Adsorbed on Highly Oriented Pyrolytic Graphite|journal=Langmuir|volume=26|issue=6|year=2010|pages=3972–3974|issn=0743-7463|doi=10.1021/la903335v}}
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.{{cite journal|doi=10.1016/0022-0248(92)90658-6|journal=Journal of Crystal Growth |volume=116 |issue=3–4 |year=1992|pages= 495–504 |title=Structure of perylene-tetracarboxylic-dianhydride thin films on alkali halide crystal substrates|author1=Möbus, M. |author2=Karl, N. |name-list-style=amp }} 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:
| class="wikitable" | ||||
| 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=
File:PTCDA AFM.jpg image of a single PTCDA molecule on Si at room temperature.{{cite journal|doi=10.1038/ncomms8766|pmid=26178193|pmc=4518281|title=Chemical structure imaging of a single molecule by atomic force microscopy at room temperature|journal=Nature Communications|volume=6|pages=7766|year=2015|last1=Iwata|first1=Kota|last2=Yamazaki|first2=Shiro|last3=Mutombo|first3=Pingo|last4=Hapala|first4=Prokop|last5=Ondráček|first5=Martin|last6=Jelínek|first6=Pavel|last7=Sugimoto|first7=Yoshiaki}}]]
File:PTCDA self-assembly STM.jpg of PTCDA molecules on NaCl, scanning tunneling microscopy image.{{cite journal|doi=10.1038/ncomms9312|pmid=26440933|pmc=4600718|title=Pronounced polarization-induced energy level shifts at boundaries of organic semiconductor nanostructures|journal=Nature Communications|volume=6|pages=8312|year=2015|last1=Cochrane|first1=K. A.|last2=Schiffrin|first2=A.|last3=Roussy|first3=T. S.|last4=Capsoni|first4=M.|last5=Burke|first5=S. A.}}]]
Use
The main industrial use of PTCDA is as a precursor to Rylene dyes.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}}
References
{{Commons category|PTCDA}}
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{{Vat dyes}}
{{dyeing}}