PTCDA

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Structural formula
Structure of PTCDA
General
Surname PTCDA
other names
  • 3,4,9,10-perylene tetracarboxylic acid dianhydride
  • CI 71127
  • CI Pigment Red 224
Molecular formula C 24 H 8 O 6
Brief description

dark red solid

External identifiers / databases
CAS number 128-69-8
EC number 204-905-3
ECHA InfoCard 100.004.461
PubChem 67191
Wikidata Q905520
properties
Molar mass 392.32 g mol −1
Physical state

firmly

Melting point

> 300 ° C

solubility
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3,4,9,10-Perylenetetracarboxylic acid dianhydride ( PTCDA ) is a pigment used in the development of organic semiconductor devices and manufactured by the colorant industry for commercial applications.

structure

Its molecular structure is based on the polycyclic aromatic hydrocarbon perylene . Two modifications of the crystal structure are known (alpha and beta). The two-dimensional structure of PTCDA layers, which can be generated by molecular beam epitaxy , was examined in detail using scanning tunneling microscopy on various substrates , including graphite , molybdenum disulfide (MoS 2 ), copper and silver. In addition to these metallic substrates, the epitaxy on various insulator surfaces such as NaCl, KCl and KBr was also investigated.

properties

Pigment red 224

PTCDA is a planar molecule with a two-dimensional conjugated π-electron system, which is delocalized over the entire perylene structure. The anhydride is an organic semiconductor (n-conductor) from the group of two-dimensionally condensed ring systems.

use

As an organic semiconductor , PTCDA can be used e.g. B. use for the production of organic field effect transistors . Derivatives of PTCDA can be used as layer in organic solar cells use or serve as adsorbate to sensitization of titanium dioxide solar cells for visible light . PTCDA is also suitable as a photocatalyst for oxygen production from water using solar energy .

As a pigment , PTCDA is mainly used in high-quality industrial paints , especially in the automotive sector.

Individual evidence

  1. ↑ a b c data sheet Perylene-3,4,9,10-tetracarboxylic dianhydride from Sigma-Aldrich , accessed on November 5, 2018 ( PDF ).
  2. ↑ a b Entry on perylene-3,4,9,10-tetracarboxylic acid dianhydride. In: Römpp Online . Georg Thieme Verlag, accessed on March 28, 2014.
  3. ↑ a b c Chun Ming Jiao, Bing Jun Li, Si Li Yi, Qing Xu: Synthesis and Photoelectric Properties of Donor-Acceptor-Donor Molecule Containing Perylene Diimide . In: Asian Journal of Chemistry . 26, No. 23, 2014, pp. 8049-8052. doi : 10.14233 / ajchem.2014.17040 .
  4. ↑ T. Ogawa et al .: 3,4: 9,10-Perylenetetracarboxylic dianhydride (PTCDA) by electron crystallography . In: Acta Cryst. B55, 1999, pp. 123-130.
  5. ↑ HP Wagner et al .: Exciton emission in PTCDA films and PTCDA / Alq3 multilayers . In: Physical Review B 70, 2004, p. 235201.
  6. ^ C. Ludwig et al .: STM investigations of PTCDA and PTCDI on graphite and MoS2. A systematic study of epitaxy and STM image contrast . In: Z. Phys. B 93, 1994, pp. 365-373.
  7. ^ Wagner et al .: The initial growth of PTCDA on Cu (111) studied by STM in J. Phys .: Condens. Matter 19, 2007, p. 056009 doi : 10.1088 / 0953-8984 / 19/5/056009
  8. ↑ Ikonomov et al .: Highly ordered thin films of perylene-3,4,9,10-tetracarboxylic acid dianhydride (PTCDA) on Ag (100) in Surface Science 602, 2008, pp 2061 .
  9. ↑ Burke et al., Phys. Rev. Lett. 100, 186104 (2008).
  10. ↑ Le Moal et al., Phys. Rev. B 82, 045301 (2010).
  11. ↑ Dienel et al., Adv. Mater. 20, 959 (2008).
  12. ↑ Müller et al., Surface Science 605, 1090 (2011).
  13. ↑ Kunstmann et al., Phys. Rev. B 71, 121403 (2005).
  14. ↑ T. Ertl. In: Alkali metal doping of perylenetetracarboxylic dianhydride (PTCDA) , Dissertation, 2001, p. 15
  15. ↑ R. Hudej, G. Bratina: Electronic transport in perylenetetracarboxylic dianhydride: The role of In diffusion . In: J. Vac. Sci. Technol. A 20, No. 3, 2002, pp. 797-801 (2002).
  16. ↑ A. Dodabalapur et al .: M olecular Orbital Energy Level Engineering in Organic Transistors . In: Advanced Materials 8, No. 10, 1996, pp. 853-855.
  17. ↑ CW Tang: Two-layer organic photovoltaic cell . In: Appl. Phys. Lett. 48, No. 2, 1986, pp. 183-185.
  18. ^ S. Ferrere, BA Gregg: New perylenes for dye sensitization of TiO 2 . In: New J. Chem. 26, 2002, pp. 1155-1160.
  19. ↑ CA Linkous, D. K Slattery: Solar photocatalytic hydrogen production from water using a dual bed photosystem (PDF; 86 kB) . In: Proceedings of the 2000 Hydrogen Program Annual Review, Volume I.
  20. ↑ W. Herbst, K. Hunger: Industrial organic pigments. Production, properties, application . 2nd edition, Wiley-VCH, Weinheim 1995, ISBN 3-527-28744-2 .