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start placeholder on important precursor to dyes and pigments, surprised we dont have this already
 
 
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{{Chembox
{{Chembox
| ImageFile = Perylenetetracarboxylic dianhydride.png
| ImageFile = Perylenetetracarboxylic dianhydride.png
| ImageSize =
| ImageSize = 220
| ImageAlt =
| ImageAlt = Skeletal formula of PTCDA
| ImageFile1 = PeryleneDianhydSample.JPG
| IUPACName =
| 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
| OtherNames = Perylene-3,4,9,10-tetracarboxylic dianhydride, Pigment Red 224
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 128-69-8
| CASNo = 128-69-8
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| PubChem =
| SMILES = }}
| UNII = NH27FW2PET
| EINECS = 204-905-3
⚫
| Section2 = {{Chembox Properties
⚫
| PubChem = 67191
⚫
| Formula = C<sub>24</sub>H<sub>8</sub>O<sub>6</sub>
| MolarMass = 392.32
| ChemSpiderID = 60534
| SMILES = c1cc2c3c(ccc4c3c1c5ccc6c7c5c4ccc7C(=O)OC6=O)C(=O)OC2=O
| Appearance =
| 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
| Density =
| InChIKey = CLYVDMAATCIVBF-UHFFFAOYAS
| MeltingPt =
| 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
⚫
| BoilingPt =
| StdInChIKey = CLYVDMAATCIVBF-UHFFFAOYSA-N }}
⚫
| Solubility = }}
| Section3 = {{Chembox Hazards
|Section2={{Chembox Properties
⚫
| Formula = C<sub>24</sub>H<sub>8</sub>O<sub>6</sub>
⚫
| MainHazards =
| FlashPt =
| MolarMass = 392.32
| Autoignition = }}
| Appearance =
| Density = 1.7 g/cm<sup>3</sup>
| MeltingPt = ~350 °C<ref>[http://123.56.90.132/en/chem/PTCDA PTCDA].</ref>
⚫
| BoilingPt =
⚫
| Solubility = }}
⚫
| Section3 = {{Chembox Structure
| CrystalStruct = [[Monoclinic]], P2<sub>1</sub>/c
| MolShape =
}}
|Section7={{Chembox Hazards
⚫
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
}}


'''Perylenetetracarboxylic dianhydride''' ('''PTCDA''') is an [[organic compound|organic]] dye molecule and an [[organic semiconductor]]. It is used as a precursor to a class of molecules known as [[Rylene dye]]s, which are useful as [[pigments]] and [[dye]]s. It is a dark red solid with low solubility in aromatic solvents. The compound has attracted much interest as an organic semiconductor.<ref name="RussellBlunt2010">{{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}}</ref>
⚫
'''Perylenetetracarboxylic dianhydride''' (PTCDA) is an [[organic compound]] used as a precursor to pigment]]s and [[dye]]. It is generated by oxidative fusion of naphthalene dicarboxylic anhydride. PTCDA reacts with amines to give a wide range of useful colorants.<ref name=Ullmann1>K. Hunger. W. Herbst "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2012. {{DOI|10.1002/14356007.a20_371}}</ref><ref>Greene, M. "Perylene Pigments" in High Performance Pigments, 2009, Wiley-VCH, Weinheim. {{DOI|10.1002/9783527626915.ch16}}

pp. 261-274.</ref>
== Structure ==
PTCDA consists of a [[perylene]] core to which two [[Organic acid anhydride|anhydride]] groups have been attached, one at either side. It occurs in two crystalline forms, α and β.<ref>{{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 }}</ref> Both have the P2<sub>1</sub>/c [[monoclinic]] symmetry and a density of ca. 1.7 g/cm<sup>3</sup>, which is relatively high for organic compounds. Their lattice parameters are:

{| class="wikitable"
|-
! Form !! a !! b !! c !! γ
|-
| α || 0.374&nbsp;nm || 1.196&nbsp;nm || 1.734&nbsp;nm || 98.8°
|-
| β || 0.378&nbsp;nm || 1.930&nbsp;nm || 1.077&nbsp;nm || 83.6°
|}

===Self-assembly and films===
[[File:PTCDA AFM.jpg|thumb|left|[[Atomic force microscopy]] image of a single PTCDA molecule on Si at room temperature.<ref name="PTCDA on Si">{{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}}</ref>]]
[[File:PTCDA self-assembly STM.jpg|thumb|left|[[Self-assembly]] of PTCDA molecules on NaCl, [[scanning tunneling microscopy]] image.<ref name="PTCDA on NaCL">{{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.}}</ref>]]

==Use==

⚫
The main industrial use of PTCDA is as a precursor to [[Rylene dye]]s.<ref name=Ullmann1>Hunger, K. and Herbst, W. (2012) "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a20_371}}</ref><ref>Greene, M. (2009) "Perylene Pigments", pp. 261–274 in High Performance Pigments, Wiley-VCH, Weinheim.{{doi|10.1002/9783527626915.ch16}}</ref>


== References ==
== References ==
{{Commons category|PTCDA}}
{{reflist}}
{{reflist}}


{{Vat dyes}}
{{Vat dyes}}
{{dyeing}}
{{dyeing}}

{{organic-compound-stub}}


[[Category:Perylene dyes]]
[[Category:Perylene dyes]]
[[Category:Vat dyes]]
[[Category:Vat dyes]]
[[Category:Anhydrides]]
[[Category:Organic semiconductors]]

Latest revision as of 10:19, 12 November 2022

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 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]

Structure

[edit]

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

[edit]
Atomic force microscopy image of a single PTCDA molecule on Si at room temperature.[4]
Self-assembly of PTCDA molecules on NaCl, scanning tunneling microscopy image.[5]

Use

[edit]

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

References

[edit]
Wikimedia Commons has media related to PTCDA.
  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; 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.
  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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