Diindenoperylene

Diindenoperylene (DIP) is an organic semiconductor which receives attention because of its potential application in optoelectronics (solar cells, OLEDs) and electronics (RFID tags). DIP is a planar perylene derivative with two indeno-groups attached to opposite sides of the perylene core. Its chemical formula is C32H16, the full chemical name is diindeno[1,2,3-cd:1',2',3'-lm]perylene. Its chemical synthesis has been described.[1][2]

Diindenoperylene
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Diindeno[1,2,3-cd:1′,2′,3′-lm]perylene
Other names
Periflanthen; Periflanthene
Identifiers
3D model (JSmol)
Abbreviations DIP
ChemSpider
ECHA InfoCard 100.005.343
UNII
  • InChI=1S/C32H16/c1-2-6-18-17(5-1)21-9-13-25-27-15-11-23-19-7-3-4-8-20(19)24-12-16-28(32(27)30(23)24)26-14-10-22(18)29(21)31(25)26/h1-16H ☒N
    Key: BKMIWBZIQAAZBD-UHFFFAOYSA-N ☒N
  • InChI=1/C32H16/c1-2-6-18-17(5-1)21-9-13-25-27-15-11-23-19-7-3-4-8-20(19)24-12-16-28(32(27)30(23)24)26-14-10-22(18)29(21)31(25)26/h1-16H
    Key: BKMIWBZIQAAZBD-UHFFFAOYAB
  • C1=CC2=C3C=CC4=C5C=CC6=C7C=CC=CC7=C8C6=C5C(=C9C4=C3C(=C2C=C1)C=C9)C=C8
Properties
C32H16
Molar mass 400.480 g·mol−1
Appearance Orange solid
Boiling point >330 °C (sublimation)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Properties and uses

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/(V·s) for thin film transistors with silicon dioxide 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 above 160 °C. In thin films for growth ‘near equilibrium’ (at substrate temperature of about 130 °C) 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. E. Clar, Polycyclic hydrocarbons (Academic Press, London, New York, 1964), p. 2
  3. Dürr, A. C.; Schreiber, F.; Münch, M.; Karl, N.; Krause, B.; Kruppa, V.; Dosch, H. (2002). "High structural order in thin films of the organic semiconductor diindenoperylene". Applied Physics Letters. 81 (12): 2276. Bibcode:2002ApPhL..81.2276D. doi:10.1063/1.1508436.
  4. A. C. Dürr, Ph.D. thesis, Universität Stuttgart (2002)
  5. Heilig, M; Domhan, M; Port, H (2004). "Optical properties and morphology of thin diindenoperylene films". Journal of Luminescence. 110 (4): 290. Bibcode:2004JLum..110..290H. doi:10.1016/j.jlumin.2004.08.023.
  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, ISBN 3-540-66721-0 pp. 283 ff.
  10. Kowarik, S.; Gerlach, A.; Sellner, S.; Schreiber, F.; Cavalcanti, L.; Konovalov, O. (2006). "Real-Time Observation of Structural and Orientational Transitions during Growth of Organic Thin Films". Physical Review Letters. 96 (12): 125504. Bibcode:2006PhRvL..96l5504K. doi:10.1103/PhysRevLett.96.125504. PMID 16605925. S2CID 1223144.
  11. Dürr, A.; Schreiber, F.; Ritley, K.; Kruppa, V.; Krug, J.; Dosch, H.; Struth, B. (2003). "Rapid Roughening in Thin Film Growth of an Organic Semiconductor (Diindenoperylene)". Physical Review Letters. 90 (1): 016104. Bibcode:2003PhRvL..90a6104D. doi:10.1103/PhysRevLett.90.016104. PMID 12570630.
  12. Dürr, A.; Koch, N.; Kelsch, M.; Rühm, A.; Ghijsen, J.; Johnson, R.; Pireaux, J.-J.; Schwartz, J.; Schreiber, F.; et al. (2003). "Interplay between morphology, structure, and electronic properties at diindenoperylene-gold interfaces". Physical Review B. 68 (11): 115428. Bibcode:2003PhRvB..68k5428D. doi:10.1103/PhysRevB.68.115428.
  13. Hoshino, A; Isoda, Seiji; Kobayashi, Takashi (1991). "Epitaxial growth of organic crystals on organic substrates — polynuclear aromatic hydrocarbons". Journal of Crystal Growth. 115 (1–4): 826–830. Bibcode:1991JCrGr.115..826H. doi:10.1016/0022-0248(91)90854-X.
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