Diindenoperylene Explained
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]
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] The structure of thin DIP films has been characterized ‘post-growth’,[2] [10] [11] [12] 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.[13]
Notes and References
- J. von Braun, G. Manz, in Deutsches Reichspatentamt, Berlin. (Germany, 1934).
- E. Clar, Polycyclic hydrocarbons (Academic Press, London, New York, 1964), p. 2
- Dürr. A. C.. Schreiber. F.. Münch. M.. Karl. N.. Krause. B.. Kruppa. V.. Dosch. H.. High structural order in thin films of the organic semiconductor diindenoperylene. Applied Physics Letters. 81. 2276. 2002. 10.1063/1.1508436. 12. 2002ApPhL..81.2276D .
- A. C. Dürr, Ph.D. thesis, Universität Stuttgart (2002)
- Heilig. M. Domhan. M. Port. H. Optical properties and morphology of thin diindenoperylene films. Journal of Luminescence. 110. 290. 2004. 10.1016/j.jlumin.2004.08.023. 4. 2004JLum..110..290H .
- H. E. Simmons. (1987)
- H. Antoniadis, A. J. Bard. (Hewlett-Packard Company & The Board of Regents of The University of Palo Alto, CA, 1997)
- M. Münch, Ph.D. thesis, Universität Stuttgart (2001)
- N. Karl, in Organic Electronic Materials R. Farchioni, G. Grosso, Eds. (Springer, Berlin, 2001), vol. II, pp. 283 ff.
- Dürr. A.. Schreiber. F.. Ritley. K.. Kruppa. V.. Krug. J.. Dosch. H.. Struth. B.. Rapid Roughening in Thin Film Growth of an Organic Semiconductor (Diindenoperylene). Physical Review Letters. 90. 016104. 2003. 10.1103/PhysRevLett.90.016104. 2003PhRvL..90a6104D. 12570630. 1.
- Dürr. A.. Koch. N.. Kelsch. M.. Rühm. A.. Ghijsen. J.. Johnson. R.. Pireaux. J.-J.. Schwartz. J.. Schreiber. F.. Interplay between morphology, structure, and electronic properties at diindenoperylene-gold interfaces. Physical Review B. 68. 115428. 2003. 10.1103/PhysRevB.68.115428. 11. 2003PhRvB..68k5428D . 9. Dosch. H.. Kahn. A..
- Hoshino. A. Epitaxial growth of organic crystals on organic substrates — polynuclear aromatic hydrocarbons. Journal of Crystal Growth. 115. 1–4. 826–830. 1991. 10.1016/0022-0248(91)90854-X. 1991JCrGr.115..826H . Isoda. Seiji. Kobayashi. Takashi.
- Kowarik. S.. Gerlach. A.. Sellner. S.. Schreiber. F.. Cavalcanti. L.. Konovalov. O.. 1223144. Real-Time Observation of Structural and Orientational Transitions during Growth of Organic Thin Films. Physical Review Letters. 96. 125504. 2006. 10.1103/PhysRevLett.96.125504. 2006PhRvL..96l5504K. 12. 16605925.