Jump to content

Perylenetetracarboxylic dianhydride: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
m added IUPAC name
 
(5 intermediate revisions by 3 users not shown)
Line 9: Line 9:
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 128-69-8
| CASNo = 128-69-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = NH27FW2PET
| EINECS = 204-905-3
| EINECS = 204-905-3
| PubChem = 67191
| PubChem = 67191
Line 35: Line 37:
}}
}}


'''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.
'''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>


== Structure ==
== Structure ==
Line 55: Line 57:
==Use==
==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>
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 ==
Line 66: Line 68:
[[Category:Perylene dyes]]
[[Category:Perylene dyes]]
[[Category:Vat dyes]]
[[Category:Vat dyes]]
[[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
Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=Perylenetetracarboxylic_dianhydride&oldid=1121450800"