Rubrene

Rubrene
Skeletal formula
Space-filling model
Names
Preferred 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=1S/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 checkY
    Key: YYMBJDOZVAITBP-UHFFFAOYSA-N checkY
  • 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 (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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Rubrene (5,6,11,12-tetraphenyltetracene) is the organic compound with the formula (C18H8(C6H5)4. It is a red colored polycyclic aromatic hydrocarbon. Because of its distinctive optical and electrical properties, rubrene has been extensively studied. It has been used as a sensitiser in chemoluminescence and as a yellow light source in lightsticks.

Electronic properties

As an organic semiconductor, rubrene has been described as a "super star". Like almost many organic electronic materials, rubrene remains in the ranks of promising, not commercial. It has been intensively investigated for applications in organic light-emitting diodes (OLEDs) and organic field-effect transistors, which are the core elements of flexible displays. Single-crystal transistors have hole conductivities of 15 cm2/V.s. The high hole mobility is observed for single crystals, not films, which would be of greater interest. Rubrene is also susceptible to oxidative degradation.

Many variants of rubrene have been prepared to improve prospects for device applications.

Crystal structure

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

Synthesis

Rubrene is prepared by treating 1,1,3-Triphenyl-2-propyn-1-ol with thionyl chloride.

The resulting chloroallene undergoes dimerization and dehydrochlorination to give rubrene.

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.

References

  1. ↑ Sawatzki-Park, Michael; Wang, Shu-Jen; Kleemann, Hans; Leo, Karl (2023). "Highly Ordered Small Molecule Organic Semiconductor Thin-Films Enabling Complex, High-Performance Multi-Junction Devices". Chemical Reviews. 123 (13): 8232–8250. doi:10.1021/acs.chemrev.2c00844. PMC 10347425. PMID 37315945.
  2. ↑ Liu, Si; Wu, Hongnan; Zhang, Xiaotao; Hu, Wenping (2021). "Research progress of rubrene as an excellent multifunctional organic semiconductor". Frontiers of Physics. 16 13304. doi:10.1007/s11467-020-0993-1.
  3. ↑ McGarry, Kathryn A.; Xie, Wei; Sutton, Christopher; Risko, Chad; Wu, Yanfei; Young, Victor G.; Brédas, Jean-Luc; Frisbie, C. Daniel; Douglas, Christopher J. (2013). "Rubrene-Based Single-Crystal Organic Semiconductors: Synthesis, Electronic Structure, and Charge-Transport Properties". Chemistry of Materials. 25 (11): 2254–2263. doi:10.1021/cm400736s.
  4. ↑ Xu, Xiaotian; Xu, Jiazhen; Cai, Yuqing; Chowdhury, Nusrat; Zhang, Chi; Cahill, David G.; Chen, Liang; Frisbie, C. Daniel; Wang, Xiaojia (2025). "Phenyl Side Groups Enhance Phonon Transport in Rubrene Crystals". Journal of the American Chemical Society. 147 (46) jacs.5c15105. doi:10.1021/jacs.5c15105. PMID 41197603.
  5. ↑ Taylor, W. H. (1936). "X-ray measurements on diflavylene, rubrene, and related compounds". Zeitschrift für Kristallographie. 93 (1–6): 151. doi:10.1524/zkri.1936.93.1.151. S2CID 101491070.
  6. ↑ Akopyan, S. A.; Avoyan, R. L. and Struchkov, Yu. T. Z. Strukt. Khim. 3, 602 (1962)
  7. ↑ Henn, D. E. & Williams, W. G. (1971). "Crystallographic data for an orthorhombic form of rubrene". J. Appl. Crystallogr. 4 (3): 256. Bibcode:1971JApCr...4..256H. doi:10.1107/S0021889871006812.
  8. ↑ Bulgarovskaya, I.; Vozzhennikov, V.; Aleksandrov, S.; Belsky, V. (1983). Latv. PSR Zinat. Akad. Vestis, Fiz. Teh. Zinat. Ser. 4. 53: 115
  9. ↑ Furniss, B. Vogel's Textbook of Practical Organic Chemistry (5th ed.). pp. 840–841.
  10. ↑ Furniss, B. Vogel's Textbook of Practical Organic Chemistry (5th ed.). pp. 844–845.
  11. ↑ Richter, M. M. (2004). "Electrochemiluminescence (ECL)". Chemical Reviews. 104 (6): 3003–36. doi:10.1021/cr020373d. PMID 15186186.