Rubrene

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Rubrene
Rubrene.svg
Rubrene-3D-spacefill.png
Rubrene.jpg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-242-0
PubChem CID
  • 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 Yes check.svgY
    Key: YYMBJDOZVAITBP-UHFFFAOYSA-N Yes check.svgY
  • 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. [1]

Contents


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. [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 polymorphs of rubrene are known. Crystals grown from vapor in vacuum can be monoclinic, [5] triclinic, [6] and 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]

3-chloro-1,1,3-triphenylpropa-1,2-diene.png

The resulting chloroallene undergoes dimerization and dehydrochlorination to give rubrene. [10]

Rubrene synthesis.png

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]

Related Research Articles

<span class="mw-page-title-main">Organic electronics</span> Field of materials science

Organic electronics is a field of materials science concerning the design, synthesis, characterization, and application of organic molecules or polymers that show desirable electronic properties such as conductivity. Unlike conventional inorganic conductors and semiconductors, organic electronic materials are constructed from organic (carbon-based) molecules or polymers using synthetic strategies developed in the context of organic chemistry and polymer chemistry.

<span class="mw-page-title-main">Gallium arsenide</span> Chemical compound

Gallium arsenide (GaAs) is a III-V direct band gap semiconductor with a zinc blende crystal structure.

<span class="mw-page-title-main">Molecular-beam epitaxy</span> Crystal growth process

Molecular-beam epitaxy (MBE) is an epitaxy method for thin-film deposition of single crystals. MBE is widely used in the manufacture of semiconductor devices, including transistors, and it is considered one of the fundamental tools for the development of nanotechnologies. MBE is used to fabricate diodes and MOSFETs at microwave frequencies, and to manufacture the lasers used to read optical discs.

<span class="mw-page-title-main">Coronene</span> Chemical compound

Coronene is a polycyclic aromatic hydrocarbon (PAH) comprising seven peri-fused benzene rings. Its chemical formula is C
24
H
12
. It is a yellow material that dissolves in common solvents including benzene, toluene, and dichloromethane. Its solutions emit blue light fluorescence under UV light. It has been used as a solvent probe, similar to pyrene.

Organic semiconductors are solids whose building blocks are pi-bonded molecules or polymers made up by carbon and hydrogen atoms and – at times – heteroatoms such as nitrogen, sulfur and oxygen. They exist in the form of molecular crystals or amorphous thin films. In general, they are electrical insulators, but become semiconducting when charges are either injected from appropriate electrodes, upon doping or by photoexcitation.

<span class="mw-page-title-main">Organic field-effect transistor</span> Type of field-effect transistor

An organic field-effect transistor (OFET) is a field-effect transistor using an organic semiconductor in its channel. OFETs can be prepared either by vacuum evaporation of small molecules, by solution-casting of polymers or small molecules, or by mechanical transfer of a peeled single-crystalline organic layer onto a substrate. These devices have been developed to realize low-cost, large-area electronic products and biodegradable electronics. OFETs have been fabricated with various device geometries. The most commonly used device geometry is bottom gate with top drain and source electrodes, because this geometry is similar to the thin-film silicon transistor (TFT) using thermally grown SiO2 as gate dielectric. Organic polymers, such as poly(methyl-methacrylate) (PMMA), can also be used as dielectric. One of the benefits of OFETs, especially compared with inorganic TFTs, is their unprecedented physical flexibility, which leads to biocompatible applications, for instance in the future health care industry of personalized biomedicines and bioelectronics.

<span class="mw-page-title-main">Single crystal</span> Material with a continuous, unbroken crystal lattice

In materials science, a single crystal is a material in which the crystal lattice of the entire sample is continuous and unbroken to the edges of the sample, with no grain boundaries. The absence of the defects associated with grain boundaries can give monocrystals unique properties, particularly mechanical, optical and electrical, which can also be anisotropic, depending on the type of crystallographic structure. These properties, in addition to making some gems precious, are industrially used in technological applications, especially in optics and electronics.

<span class="mw-page-title-main">Pentacene</span> Hydrocarbon compound (C22H14) made of 5 fused benzene rings

Pentacene is a polycyclic aromatic hydrocarbon consisting of five linearly-fused benzene rings. This highly conjugated compound is an organic semiconductor. The compound generates excitons upon absorption of ultra-violet (UV) or visible light; this makes it very sensitive to oxidation. For this reason, this compound, which is a purple powder, slowly degrades upon exposure to air and light.

<span class="mw-page-title-main">Tetracene</span> Chemical compound

Tetracene, also called naphthacene, is a polycyclic aromatic hydrocarbon. It has the appearance of a pale orange powder. Tetracene is the four-ringed member of the series of acenes.

<span class="mw-page-title-main">Fluorene</span> Chemical compound

Fluorene, or 9H-fluorene is an organic compound with the formula (C6H4)2CH2. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of naphthalene. It has a violet fluorescence, hence its name. For commercial purposes it is obtained from coal tar. It is insoluble in water and soluble in many organic solvents. Although sometimes classified as a polycyclic aromatic hydrocarbon, the five-membered ring has no aromatic properties. Fluorene is mildly acidic.

<span class="mw-page-title-main">Hexacene</span> Chemical compound

Hexacene is an aromatic compound consisting of six linearly-fused benzene rings. It is a blue-green, air-stable solid with low solubility.

<span class="mw-page-title-main">Acene</span> Class of chemical compounds

In organic chemistry, the acenes or polyacenes are a class of organic compounds and polycyclic aromatic hydrocarbons made up of benzene rings which have been linearly fused. They follow the general molecular formula C4n+2H2n+4.

<span class="mw-page-title-main">Diindenoperylene</span> Chemical compound

Diindenoperylene (DIP) is an organic semiconductor which receives attention because of its potential application in optoelectronics (solar cells, OLEDs) and electronics (RFID tags). DIP is a planar perylene derivative with two indeno-groups attached to opposite sides of the perylene core. Its chemical formula is C32H16, the full chemical name is diindeno[1,2,3-cd:1',2',3'-lm]perylene. Its chemical synthesis has been described.

<span class="mw-page-title-main">Zethrene</span> Chemical compound

Zethrene (dibenzo[de,mn]naphthacene) is a polycyclic aromatic hydrocarbon consisting of two phenalene units fused together. According to Clar's rule, the two exterior naphthalene units are truly aromatic and the two central double bonds are not aromatic at all. For this reason the compound is of some interest to academic research. Zethrene has a deep-red color and it is light sensitive - complete decomposition under a sunlight lamp occurs within 12 hours. The melting point is 262 °C.

<span class="mw-page-title-main">Polyfluorene</span> Chemical compound

Polyfluorene is a polymer with formula (C13H8)n, consisting of fluorene units linked in a linear chain — specifically, at carbon atoms 2 and 7 in the standard fluorene numbering. It can also be described as a chain of benzene rings linked in para positions with an extra methylene bridge connecting every pair of rings.

<span class="mw-page-title-main">Phenacene</span> Group of chemical compounds

Phenacenes are a class of organic compounds consisting of fused aromatic rings. They are polycyclic aromatic hydrocarbons, related to acenes and helicenes from which they differ by the arrangement of the fused rings.

<span class="mw-page-title-main">Perylenetetracarboxylic dianhydride</span> Chemical compound

Perylenetetracarboxylic dianhydride (PTCDA) is an organic dye molecule and an organic semiconductor. It is used as a precursor to a class of molecules known as Rylene dyes, which are useful as pigments and dyes. It is a dark red solid with low solubility in aromatic solvents. The compound has attracted much interest as an organic semiconductor.

<span class="mw-page-title-main">Contorted aromatics</span> Hydrocarbon compounds composed of rings fused such that the molecule is nonplanar

In organic chemistry, contorted aromatics, or more precisely contorted polycyclic aromatic hydrocarbons, are polycyclic aromatic hydrocarbons (PAHs) in which the fused aromatic molecules deviate from the usual planarity.

<span class="mw-page-title-main">Klaus Müllen</span>

Klaus Müllen is a German chemist working in the fields of polymer chemistry, supramolecular chemistry and nanotechnology. He is known for the synthesis and exploration of the properties of graphene-like nanostructures and their potential applications in organic electronics.

Oana Jurchescu is a Romanian physicist who is the Baker Family Physics Professor at Wake Forest University. Her research considers charge transport in organic and organic/inorganic hybrid semiconductors. In 2022, she was awarded a National Science Foundation Special Creativity Award for her work translating organic electronic materials into real-world devices.

References

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  2. 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.
  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. 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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. 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.