Diindenoperylene

Diindenoperylene
IUPAC name Diindeno[1,2,3-cd:1',2',3'-lm]perylene
Other names Periflanthen; Periflanthene
Identifiers
Abbreviations	DIP
CAS number	188-94-3 Y
PubChem	96712
Jmol-3D images	Image 1
SMILES C1=CC2=C3C=CC4=C5C=CC6=C7C=CC=CC7=C8C6=C5C(=C9C4=C3C(=C2C=C1)C=C9)C=C8
Properties
Molecular formula	C32H16
Molar mass	400.47 g mol−1
Appearance	Orange solid
Boiling point	>330 °C (sublimation)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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]

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. ^ ^{a b c} 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. 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. 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 3540667210 pp. 283 ff.
10. ^ ^{a b} 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. 
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. et al. (2003). "Interplay between morphology, structure, and electronic properties at diindenoperylene-gold interfaces". Physical Review B 68 (11): 115428. doi:10.1103/PhysRevB.68.115428. 
13. ^ Hoshino, A (1991). "Epitaxial growth of organic crystals on organic substrates — polynuclear aromatic hydrocarbons". Journal of Crystal Growth 115: 826. doi:10.1016/0022-0248(91)90854-X.