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Rubrene

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Rubrene
Names
IUPAC name
5,6,11,12-Tetraphenyltetracene
Other names
5,6,11,12-Tetraphenylnaphthacene, rubrene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.494 Edit this at Wikidata
EC Number
  • 208-242-0
  • InChI=1/C42H28/c1-5-17-29(18-6-1)37-33-25-13-14-26-34(33)39(31-21-9-3-10-22-31)42-40(32-23-11-4-12-24-32)36-28-16-15-27-35(36)38(41(37)42)30-19-7-2-8-20-30/h1-28H
    Key: YYMBJDOZVAITBP-UHFFFAOYAD
  • c5(c3c(c1ccccc1c(c2ccccc2)c3c(c4ccccc4)c6ccccc56)c7ccccc7)c8ccccc8
Properties
C42H28
Molar mass 532.7 g/mol
Melting point 315 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rubrene (5,6,11,12-tetraphenylnaphthacene) is a red colored polycyclic aromatic hydrocarbon. Rubrene is used as a sensitiser in chemoluminescence and as a yellow light source in lightsticks.

Rubrene powder

As an organic semiconductor, the major application of rubrene is in organic light-emitting diodes (OLEDs) and organic field-effect transistors, which are the core elements of flexible displays. Single-crystal transistors can be prepared using crystalline rubrene, which is grown in a modified zone furnace on a temperature gradient. This technique, known as physical vapor transport, was introduced in 1998.[1][2]

Rubrene holds the distinction of being the organic semiconductor with the highest carrier mobility, which reaches 40 cm2/(V·s) for holes. This value was measured in OFETs prepared by peeling a thin layer of single-crystalline rubrene and transferring to a Si/SiO2 substrate.[3]

Crystal structure

Rubrene crystals are formed through competition between rather weak intermolecular interactions, namely π-stacking and quadrupolar interactions. Owing to these weak interactions, different growth conditions can lead to different crystalline structures – a phenomenon common to many organic crystals. Therefore, several polymorphs of rubrene are known for crystals grown from vapor in vacuum using sealed ampoules, including a monoclinic,[4] triclinic[5] and orthorhombic (space group Aba2) forms.[6] Another orthorhombic form (space group Bbam) is known in crystals obtained in a closed system, in a two-zone furnace, at ambient pressure.[7]

References

  1. ^ A. Laudise, C. Kloc, P. Simpkins, and T. Siegrist "Physical vapor growth of organic semiconductors" J. Cryst. Growth 187, 449 (1998) doi:10.1016/S0022-0248(98)00034-7
  2. ^ Oana Diana Jurchescu "Molecular organic semiconductors for electronic devices" chapter Low Temperature Crystal Structure of Rubrene Single Crystals Grown by Vapor Transport, PhD thesis (2006) Rijksuniversiteit Groningen
  3. ^ Tatsuo Hasegawa and Jun Takeya (2009). "Organic field-effect transistors using single crystals". Sci. Technol. Adv. Mater. 10: 024314. doi:10.1088/1468-6996/10/2/024314. {{cite journal}}: |format= requires |url= (help)
  4. ^ W. H. Taylor, Z. Kristallogr. 93, 151 (1936)
  5. ^ S. A. Akopyan, R. L. Avoyan, and Yu. T. Struchkov, Z. Strukt. Khim. 3, 602 (1962)
  6. ^ D. E. Henn, and W. G. Williams, J. Appl. Cryst. 4, 256 (1971)
  7. ^ I. Bulgarovskaya, V. Vozzhennikov, S. Aleksandrov, and V. Belsky, Latv. PSR Zinat. Akad. Vestis, Fiz. Teh. Zinat. Ser. 4, 53 (1983) 115
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