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 structureedit
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]
Synthesisedit
Rubrene is prepared by treating 1,1,3-Triphenyl-2-propyn-1-ol with thionyl chloride.[9]
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]
Referencesedit
Wikimedia Commons has media related to Rubrene.
^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. PMC10347425. PMID 37315945.
^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.
^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.
^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. PMC5090444. PMID 27877287.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^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.
^Akopyan, S. A.; Avoyan, R. L. and Struchkov, Yu. T. Z. Strukt. Khim. 3, 602 (1962)
^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.
^Furniss, B. Vogel's Textbook of Practical Organic Chemistry (5th ed.). pp. 840–841.
^Furniss, B. Vogel's Textbook of Practical Organic Chemistry (5th ed.). pp. 844–845.
^Richter, M. M. (2004). "Electrochemiluminescence (ECL)". Chemical Reviews. 104 (6): 3003–36. doi:10.1021/cr020373d. PMID 15186186.
January 01, 1970
rubrene, tetraphenyltetracene, organic, compound, with, formula, c18h8, c6h5, colored, polycyclic, aromatic, hydrocarbon, because, distinctive, optical, electrical, properties, rubrene, been, extensively, studied, been, used, sensitiser, chemoluminescence, yel. 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 Rubrene Names Preferred IUPAC name 5 6 11 12 Tetraphenyltetracene Other names 5 6 11 12 Tetraphenylnaphthacene rubrene Identifiers CAS Number 517 51 1 Y 3D model JSmol Interactive image ChemSpider 61510 Y ECHA InfoCard 100 007 494 EC Number 208 242 0 PubChem CID 68203 CompTox Dashboard EPA DTXSID8060161 InChI 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 YKey YYMBJDOZVAITBP UHFFFAOYSA N YInChI 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 28HKey YYMBJDOZVAITBP UHFFFAOYAD SMILES c5 c3c c1ccccc1c c2ccccc2 c3c c4ccccc4 c6ccccc56 c7ccccc7 c8ccccc8 Properties Chemical formula 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 Y verify what is Y N Infobox references Contents 1 Electronic properties 2 Crystal structure 3 Synthesis 4 Redox properties 5 ReferencesElectronic properties editAs 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 editSeveral 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 editRubrene is prepared by treating 1 1 3 Triphenyl 2 propyn 1 ol with thionyl chloride 9 nbsp The resulting chloroallene undergoes dimerization and dehydrochlorination to give rubrene 10 nbsp Redox properties editRubrene 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 edit nbsp Wikimedia Commons has media related to Rubrene 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 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 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 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 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Taylor W H 1936 X ray measurements on diflavylene rubrene and related compounds Zeitschrift fur Kristallographie 93 1 6 151 doi 10 1524 zkri 1936 93 1 151 S2CID 101491070 Akopyan S A Avoyan R L and Struchkov Yu T Z Strukt Khim 3 602 1962 Henn D E amp Williams W G 1971 Crystallographic data for an orthorhombic form of rubrene J Appl Crystallogr 4 3 256 doi 10 1107 S0021889871006812 Bulgarovskaya I Vozzhennikov V Aleksandrov S Belsky V 1983 Latv PSR Zinat Akad Vestis Fiz Teh Zinat Ser 4 53 115 Furniss B Vogel s Textbook of Practical Organic Chemistry 5th ed pp 840 841 Furniss B Vogel s Textbook of Practical Organic Chemistry 5th ed pp 844 845 Richter M M 2004 Electrochemiluminescence ECL Chemical Reviews 104 6 3003 36 doi 10 1021 cr020373d PMID 15186186 Retrieved from https en wikipedia org w index php title Rubrene amp oldid 1215499223, wikipedia, wiki, book, books, library,
