Rubrene

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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).
checkY verify (what is checkY☒N ?)

Rubrene (5,6,11,12-tetraphenyltetracene) is the

lightsticks.[1]


Electronic properties

As an

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.[2][3]

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.[4]

Crystal structure

Several

orthorhombic motifs.[7] Orthorhombic crystals (space group Bbam) are obtained in a closed system in a two-zone furnace at ambient pressure.[8]

Synthesis

Rubrene is prepared by treating 1,1,3-Triphenyl-2-propyn-1-ol with thionyl chloride.[9]

The resulting chloro

dehydrochlorination to give rubrene.[10]

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.[11]

References

Wikimedia Commons has media related to Rubrene.
  1. PMID 37315945
    .
  2. doi:10.1016/S0022-0248(98)00034-7
    .
  3. ^ 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.
  4. PMID 27877287.{{cite journal}}: CS1 maint: multiple names: authors list (link
    )
  5. S2CID 101491070
    .
  6. ^ Akopyan, S. A.; Avoyan, R. L. and Struchkov, Yu. T. Z. Strukt. Khim. 3, 602 (1962)
  7. 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. PMID 15186186
    .
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