Rubrene

Rubrene (5,6,11,12-tetraphenyltetracene) is a red colored polycyclic aromatic hydrocarbon. Rubrene is used as a sensitiser in chemoluminescence and as a yellow light source in lightsticks.

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
EC Number
  • 208-242-0
Properties
C42H28
Molar mass 532.7 g/mol
Melting point 315 °C (599 °F; 588 K)
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

Electronic properties

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, reaching 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

Several polymorphs of rubrene are known. Crystals grown from vapor in vacuum can be monoclinic,[4] triclinic,[5] and orthorhombic motifs.[6] Orthorhombic crystals (space group Bbam) are obtained in a closed system in a two-zone furnace at ambient pressure.[7]

Synthesis

Rubrene is prepared by treating 1,1,3-triphenylprop-2-yne-1-ol with thionyl chloride.[8]

The resulting chloroallene undergoes dimerization and dehydrochlorination to give rubrene.[9]

Redox properties

Rubrene, like other polycyclic aromatic molecules, undergoes redox reactions in solution. It oxidizes and reduces reversibly at 0.95 V and −1.37 V, respectively vs SCE. When the cation and anion are co-generated in an electrochemical cell, they can combine with annihilation of their charges, but producing an excited rubrene molecule that emits at 540 nm. This phenomenon is called electrochemiluminescence.[10]

References
  1. Laudise, R.A; Kloc, Ch; Simpkins, P.G; Siegrist, T (1998). "Physical vapor growth of organic semiconductors". Journal of Crystal Growth. 187 (3–4): 449. Bibcode:1998JCrGr.187..449L. doi:10.1016/S0022-0248(98)00034-7.
  2. Jurchescu, Oana Diana (2006) "Low Temperature Crystal Structure of Rubrene Single Crystals Grown by Vapor Transport" in Molecular organic semiconductors for electronic devices, PhD thesis Rijksuniversiteit Groningen.
  3. Hasegawa, Tatsuo and Takeya, Jun (2009). "Organic field-effect transistors using single crystals". Sci. Technol. Adv. Mater. 10 (2): 024314. Bibcode:2009STAdM..10b4314H. doi:10.1088/1468-6996/10/2/024314. PMC 5090444. PMID 27877287.CS1 maint: multiple names: authors list (link)
  4. Taylor, W. H. (1936). "X-ray measurements on diflavylene, rubrene, and related compounds". Zeitschrift für Kristallographie. 93: 151. doi:10.1524/zkri.1936.93.1.151.
  5. Akopyan, S. A.; Avoyan, R. L. and Struchkov, Yu. T. Z. Strukt. Khim. 3, 602 (1962)
  6. Henn, D. E. & Williams, W. G. (1971). "Crystallographic data for an orthorhombic form of rubrene". J. Appl. Cryst. 4 (3): 256. doi:10.1107/S0021889871006812.
  7. Bulgarovskaya, I.; Vozzhennikov, V.; Aleksandrov, S.; Belsky, V. (1983). Latv. PSR Zinat. Akad. Vestis, Fiz. Teh. Zinat. Ser. 4. 53: 115
  8. Furniss, B. Vogel's Textbook of Practical Organic Chemistry (5th ed.). pp. 840–841.
  9. Furniss, B. Vogel's Textbook of Practical Organic Chemistry (5th ed.). pp. 844–845.
  10. Richter, M. M. (2004). "Electrochemiluminescence (ECL)". Chemical Reviews. 104 (6): 3003–36. doi:10.1021/cr020373d. PMID 15186186.
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