Rubrene

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.{{cite journal|doi=10.1016/S0022-0248(98)00034-7|title=Physical vapor growth of organic semiconductors|journal=Journal of Crystal Growth|volume=187|issue=3–4|pages=449|year=1998|last1=Laudise|first1=R.A|last2=Kloc|first2=Ch|last3=Simpkins|first3=P.G|last4=Siegrist|first4=T|bibcode=1998JCrGr.187..449L}}Jurchescu, Oana Diana (2006) [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"] in Molecular organic semiconductors for electronic devices, PhD thesis Rijksuniversiteit Groningen.

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.{{cite journal |journal=Science and Technology of Advanced Materials |volume=10 |issue=2 |date=6 July 2009 |article-number=024314 |title=Organic field-effect transistors using single crystals |last1=Hasegawa |first1=Tatsuo |last2=Takeya |first2=Jun |bibcode=2009STAdM..10b4314H |doi=10.1088/1468-6996/10/2/024314 |pmc=5090444 |pmid=27877287 }}

Several polymorphs of rubrene are known. Crystals grown from vapor in vacuum can be monoclinic,{{cite journal|author=Taylor, W. H.|journal= Zeitschrift für Kristallographie|title= X-ray measurements on diflavylene, rubrene, and related compounds|volume= 93|page= 151|date=1936|issue= 1–6|doi=10.1524/zkri.1936.93.1.151|s2cid= 101491070}} triclinic,Akopyan, S. A.; Avoyan, R. L. and Struchkov, Yu. T. Z. Strukt. Khim. 3, 602 (1962) and orthorhombic motifs.{{cite journal|author=Henn, D. E.|author2=Williams, W. G.|name-list-style=amp |journal= J. Appl. Crystallogr.|doi=10.1107/S0021889871006812|title=Crystallographic data for an orthorhombic form of rubrene|volume= 4|page= 256 |date=1971|issue=3}} Orthorhombic crystals (space group B_bam) are obtained in a closed system in a two-zone furnace at ambient pressure.Bulgarovskaya, I.; Vozzhennikov, V.; Aleksandrov, S.; Belsky, V. (1983). Latv. PSR Zinat. Akad. Vestis, Fiz. Teh. Zinat. Ser. 4. 53: 115

Rubrene is prepared by treating 1,1,3-Triphenyl-2-propyn-1-ol with thionyl chloride.{{cite book |first=B.|last=Furniss|title = Vogel's Textbook of Practical Organic Chemistry|edition=5th|pages=840–841}}

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The resulting chloroallene undergoes dimerization and dehydrochlorination to give rubrene.{{cite book |first=B.|last=Furniss|title = Vogel's Textbook of Practical Organic Chemistry|edition=5th|pages=844–845}}

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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.{{cite journal|author=Richter, M. M.|title=Electrochemiluminescence (ECL)|journal=Chemical Reviews|volume=104|issue=6|pages=3003–36|doi=10.1021/cr020373d|pmid=15186186|year=2004}}

{{Commons category|Rubrene}}

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Category:Polycyclic aromatic hydrocarbons

Category:Organic semiconductors

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