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| OtherNames = 5,6,11,12-Tetraphenylnaphthacene, rubrene
| OtherNames = 5,6,11,12-Tetraphenylnaphthacene, rubrene
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite}}
| CASNo_Ref = {{cascite}}
| CASNo = 517-51-1
| CASNo = 517-51-1
| EINECS = 208-242-0
| EINECS = 208-242-0
| PubChem = 68203
| PubChem = 68203
| SMILES = c34c(c7ccccc7)c2c(c8ccccc8)c1ccccc1
| SMILES = c34c(c7ccccc7)c2c(c8ccccc8)c1ccccc1
c(c6ccccc6)c2c(c5ccccc5)c3cccc4
c(c6ccccc6)c2c(c5ccccc5)c3cccc4
}}
}}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| Formula = C<sub>42</sub>H<sub>28</sub>
| Formula = C<sub>42</sub>H<sub>28</sub>
| MolarMass = 532.7 g/mol
| MolarMass = 532.7 g/mol
| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt = 315 °C
| MeltingPt = 315 °C
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility =
}}
}}
| Section3 = {{Chembox Hazards
| Section3 = {{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition =
| Autoignition =
⚫
}}
}}
}}
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}}

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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 [[lightstick]]s.


⚫
[[Image:Rubrene.jpg|thumb|right|Rubrene powder]]
⚫
'''Rubrene''' ('''5,6,11,12-tetraphenylnaphthacene''') is a red colored [[polycyclic aromatic hydrocarbon]]. It has the appearance of a red crystalline powder. Rubrene is used as a [[sensitiser]] in [[chemoluminescence]]. In [[lightstick]]s it is used to produce yellow light.


⚫
As an [[organic semiconductor]], the major application of rubrene is in [[Organic LED|organic light-emitting diode]]s (OLEDs) and [[organic field-effect transistor]]s, 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.<ref>A. Laudise, C. Kloc, P. Simpkins, and T. Siegrist "Physical vapor growth of organic semiconductors" J. Cryst. Growth 187, 449
⚫
[[Image:Rubrene.jpg|thumb|right|photograph of rubrene crystals]]
(1998) {{doi|10.1016/S0022-0248(98)00034-7}}</ref><ref>Oana Diana Jurchescu "Molecular organic semiconductors for electronic devices" chapter [http://dissertations.ub.rug.nl/FILES/faculties/science/2006/o.d.jurchescu/06_c6.pdf Low Temperature Crystal Structure of Rubrene Single Crystals Grown by Vapor Transport], PhD thesis (2006) Rijksuniversiteit Groningen</ref>


Rubrene holds the distinction of being organic semiconductor with the highest carrier mobility, which reaches 40 cm<sup>2</sup>/(V·s) for electrons. This value was measured in OFETs prepared by peeling a thin layer of single-crystalline rubrene and transferring to a Si/SiO<sub>2</sub> substrate.<ref name=sc>{{cite journal|format=free download review|journal=Sci. Technol. Adv. Mater. |volume=10|year=2009|page= 024314|doi=10.1088/1468-6996/10/2/024314|title=Organic field-effect transistors using single crystals|author=Tatsuo Hasegawa and Jun Takeya}}</ref>
⚫
Rubrene is an [[organic semiconductor]], used in [[Organic light-emitting diode|OLEDs]] and OLED-based displays. Single-crystal [[transistors]] can be prepared using crystalline rubrene. Crystals of rubrene and other organic semiconductors are generally grown in a modified zone furnace on a temperature gradient, by a technique known as Physical Vapor Transport. This method was introduced in 1997 by R. A. Laudise, Christian Kloc ''et al.''


==Crystal structure==
Rubrene holds the distinction of being the highest mobility organic semiconductor, with Podzorov ''et al.'' recording room-temperature field-effect mobilities of ~30<math>cm^2/Vs </math> along the crystallographic b-axis using a novel air-gap dielectric architecture. It has also been employed to demonstrate the [[Hall Effect]] in rubrene, cited (along with photoconductivity experiments) as evidence of diffusive, band-type transport in organic crystals.
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 phenonmenon common to many organic crystals. Therefore, several [[polymorph]]s of rubrene are known for crystals grown
from vapor in vacuum using sealed ampoules, including a [[monoclinic]],<ref>W. H. Taylor, Z. Kristallogr. 93, 151 (1936)</ref> [[triclinic]]<ref>S. A. Akopyan, R. L. Avoyan, and Yu. T. Struchkov, Z. Strukt. Khim. 3, 602
(1962)</ref> and [[orthorhombic]] (space group Aba2) forms.<ref>D. E. Henn, and W. G. Williams, J. Appl. Cryst. 4, 256 (1971)</ref> Another orthorhombic form (space group Bbam) is known in crystals obtained in a closed system, in a two-zone furnace, at ambient pressure.<ref>I. Bulgarovskaya, V. Vozzhennikov, S. Aleksandrov, and V. Belsky, Latv. PSR Zinat. Akad. Vestis, Fiz. Teh. Zinat. Ser. 4, 53 (1983) 115</ref>


==References==
==References==
{{reflist}}
*{{cite journal | author = Darmanyan A. P. | date = August 1982 | title = Nature of lasting luminescence of rubrene in solution | journal = Russian Chemical Bulletin | volume = 31 | issue = 8 | pages = 1679–1682(4) | pmid = | doi = 10.1007/BF00956909 | url = http://www.springerlink.com/content/nwult88620538056/ | accessdate = 2007-07-05 }}
*{{cite journal | author = Zhang Zhi-lin et al. | date = 1998 | title = The effect of rubrene as a dopant on the efficiency and stability of organic thin film electroluminescent devices | journal = J. Phys. D: Appl. Phys. | volume = 31 | issue = 1 | pages = 32–35(4) | pmid = | doi = 10.1088/0022-3727/31/1/005 | url = http://www.iop.org/EJ/abstract/0022-3727/31/1/005 | accessdate = 2007-07-05 | format = abstract }}
*{{cite journal | author = Silva Filho D. A. da, Kim E.-G., Brédas J.-L. | date = 2005 | title = Transport Properties in the Rubrene Crystal: Electronic Coupling and Vibrational Reorganization Energy | journal = Advanced Materials | volume = 17 | issue = 8 | pages = 1072–1076(5) | pmid = | doi = 10.1002/adma.200401866 | url = http://www3.interscience.wiley.com/cgi-bin/abstract/110438510/ABSTRACT | accessdate = 2007-07-05 | format = abstract }}
*{{cite journal | url=http://www.nature.com/nature/journal/v451/n7177/full/451408a.html | title=Materials science: Lilliputian light sticks | accessdate=2008-04-15 | doi=10.1038/451408a | year=2008 | author=Fardy, Melissa | journal=Nature | volume=451 | pages=408}}
==External links==
*[http://www.tnt2006.org/Abstracts/Posters/TNT2006_LuoYi.pdf AFM and SEM study of rubrene micro-crystal thin film and nanowires growth]


[[Category:Polycyclic aromatic hydrocarbons]]
[[Category:Polycyclic aromatic hydrocarbons]]

Revision as of 10:17, 15 February 2010

Rubrene
Names
IUPAC name
5,6,11,12-Tetraphenyltetracene
Other names
5,6,11,12-Tetraphenylnaphthacene, rubrene
Identifiers
3D model (JSmol)
ECHA InfoCard 100.007.494 Edit this at Wikidata
EC Number
  • 208-242-0
  • c34c(c7ccccc7)c2c(c8ccccc8)c1ccccc1 c(c6ccccc6)c2c(c5ccccc5)c3cccc4
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 organic semiconductor with the highest carrier mobility, which reaches 40 cm2/(V·s) for electrons. 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 phenonmenon 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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