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Diindenoperylene



chemical formula C32H16
colour orange


molecular weight 400.48 g/mol
sublimation temperature > 330 °C



diindenoperylene is an organic compound.Organic semiconductors such as pentacene and diindenoperylene (DIP) receive increasing attention because of numerous applications in optoelectronics (solar cells, OLEDs) and electronics (RFID tags). The organic semiconductor DIP is a planar perylene derivative with two indeno-groups attached to opposite sides of the perylene core as pictured in Figure 1, which shows a wireframe model of DIP and the approximate van-der-Waals radii (shadowed area). Its chemical formula is C32H16, the full chemical name is diindeno[1,2,3-cd:1',2',3'-lm]perylene (8CI9CI), an alternate name is periflanthene. Its chemical synthesis has been described [1] [2]


The molecular weight is 400.48 g/mol, the dimensions of the molecule in its plane are ~18.4  7 Å [3] and its sublimation temperature is above 330 °C [4]. It is non-polar and therefore only slightly soluble, for example in acetone.

DIP is a red dye [5] and has been used as active material for optical recording [6]. Because of its ‘perylene-type’ optical emission in the visible spectrum it has also been used in organic light emitting diodes [7]. Organic field effect transistors of DIP have been studied [8]. The charge carrier mobility achieved was up to 0.1 cm2 / (Vs) for thin film transistors with silicon oxide as gate dielectric, making DIP a good candidate for further optimisation [9].

The structure of bulk DIP crystals has recently been studied by Pflaum et al., who found two distinct phases at room temperature and at temperatures >160 °C. In thin films for growth ‘near equilibrium’ (high T, i.e.,~130 °C substrate temperature) by organic molecular beam deposition (OMBD), DIP has been shown to order very well [2] [10]. The structure of thin DIP films has been characterized ‘post-growth’ [2] [11][12] [13], with structures differing from the room-temperature bulk structure. These thin-film structures depend on the substrate used, and also on the substrate temperature during growth [10].

References

  1. ^ J. von Braun, G. Manz, in Deutsches Reichspatentamt, Berlin. (Germany, 1934).
  2. ^ a b c E. Clar, Polycyclic hydrocarbons (Academic Press, London, New York, 1964), pp. 2 v.
  3. ^ A. C. Dürr et al., Applied Physics Letters 81, 2276 (Sep 16, 2002).
  4. ^ A. C. Dürr, Ph.D. thesis, Universität Stuttgart (2002).
  5. ^ M. Heilig, M. Domhan, H. Port, 110, 290 (Dec, 2004).
  6. ^ H. E. Simmons. (1987).
  7. ^ H. Antoniadis, A. J. Bard. (Hewlett-Packard Company & The Board of Regents of The University of Palo Alto, CA, 1997).
  8. ^ M. Münch, Ph.D. thesis, Universität Stuttgart (2001).
  9. ^ N. Karl, in Organic Electronic Materials R. Farchioni, G. Grosso, Eds. (Springer, Berlin, 2001), vol. II.
  10. ^ a b S. Kowarik et al., Physical Review Letters 96, 125504 (2006).
  11. ^ A. C. Dürr et al., Physical Review Letters 90, 016104 (Jan 10, 2003).
  12. ^ A. C. Dürr et al., Physical Review B 68, 115428/1 (2003).
  13. ^ A. Hoshino, S. Isoda, T. Kobayashi, Journal of Crystal Growth 115, 826 (1991///, 1991).
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Diindenoperylene". A list of authors is available in Wikipedia.
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