517-51-1 Usage
Description
Rubrene, a molecule with a tetracene backbone and four appended phenyl rings, is one of the most studied molecular semiconductors due to its high charge mobility. Notably, room-temperature hole mobilities of the order of 20-40 cm2V-1s-1 have been measured for rubrene in single-crystal organic field-effect transistors (SC-OFET). It is widely used in organic electronics, especially organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs).
Chemical Properties
red crystalline powder
Uses
Rubrene is an organic semiconductor used in organic light-emitting diodes (OLEDs) and organic field-effect transistors. It is used as a sensitizer in chemoluminesence. It is also used to prepare single crystal transistors. It acts as a reagent for chemiluminescence research and for transition metal complex ligation. Further, it is used as a p-type organic semiconductor.
Preparation
Rubrene is an organic molecule that has long been known for its outstanding semiconductor performance in organic electronic devices.Rubrene is prepared by treating 1,1,3-triphenylprop-2-yne-1-ol with thionyl chloride.The resulting chloroallene undergoes dimerization and dehydrochlorination to give rubrene.
General Description
Rubrene is a tetraphenyl derivative of tetracene that is used as an organic semiconductor. It is used as a source material in the fabrication of rubrene single crystal based transistors with carrier mobility over 10 cm2V?1s?1.
Purification Methods
It has also been recrystallised from *benzene under red light because it is chemiluminescent and light sensitive. [Beilstein 5 IV 2968.]
Structure and conformation
The rubrene molecule is basically the tetracene molecule with four wings. Its family are the polycyclic aromatic hydrocarbons. When rubrene molecules combine to build orthorhombic crystals, the molecules have a centrosymmetric structure with 2/m symmetry, as shown in the figure (their tetracene backbone acquires a twist when the molecules are free from constrains). Symmetry considerations imply that transitions between electronic ground state and first excited state can only be mediated by electromagnetic radiation that is polarized parallel to the 2-fold symmetry axis of the molecule (the M axis), which is in the plane of the tetracene backbone and perpendicular to its long axis.https://www.lehigh.edu/~inlo/rubrene.html
Check Digit Verification of cas no
The CAS Registry Mumber 517-51-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 7 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 517-51:
(5*5)+(4*1)+(3*7)+(2*5)+(1*1)=61
61 % 10 = 1
So 517-51-1 is a valid CAS Registry Number.
InChI: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
517-51-1Relevant articles and documents
Oxidation of rubrene, and implications for device stability
Ly, Jack T.,Lopez, Steven A.,Lin, Janice B.,Kim, Jae Joon,Lee, Hyunbok,Burnett, Edmund K.,Zhang, Lei,Aspuru-Guzik, Alán,Houk,Briseno, Alejandro L.
, p. 3757 - 3761 (2018/04/12)
The rapid spontaneous photo-oxidation of rubrene to form endo-peroxide, rubrene-Ox1, was monitored via1H NMR and UV-vis spectroscopy. The reaction is thermally reversible, which restores high mobility devices in both the crystalline thin film and single crystal. Prolonged stirring in chlorinated solvents yields a secondary, irreversible product, rubrene-Ox2, which has lost phenol, as confirmed by single crystal analysis. An acid-catalyzed rearrangement of the endo-peroxide to form rubrene-Ox2 was identified here with Density Functional Theory (DFT). Implications of the nature of these processes for the preparation of organic transistors are described.
The rubrenic synthesis: The delicate equilibrium between tetracene and cyclobutene
Braga, Daniele,Jaafari, Abdelhafid,Miozzo, Luciano,Moret, Massimo,Rizzato, Silvia,Papagni, Antonio,Yassar, Abderrahim
, p. 4160 - 4169 (2011/10/01)
Herein we describe the synthesis of new substituted tetraaryltetracenes, obtained by the dimerization of triarylchloroallenes, prepared from propargyl alcohols. The propargyl alcohols were prepared by two different synthetic strategies and then the alcohols were treated to obtain the corresponding acenes. In addition to the expected tetracene derivatives, we observed the formation of bis(alkylidene)cyclobutenes. When strong electron-donating substituents were present, the main product was the cyclobutene. We discuss a reaction mechanism that accounts for the formation of the cyclobutenes.
Synthesis process
-
Page/Page column 5, (2008/06/13)
A process for synthesizing a naphthacene compound comprises the steps of: (a) reacting a propargyl alcohol compound with a reagent capable of forming a leaving group to form a reaction mixture containing an intermediate; and then (b) heating the intermediate in the presence of a solvent and in the absence of any oxidizing agent and in the absence of any base, to form the naphthacene compound.
