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932450

Sigma-Aldrich

Rubrene

≥99% (HPLC)

Synonym(s):

Naphthacene, Rubrene, 5,6,11,12-Tetraphenylnaphthacene

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About This Item

Empirical Formula (Hill Notation):
C42H28
CAS Number:
517-51-1
Molecular Weight:
532.67
Beilstein:
1917339
MDL number:
MFCD00003703
UNSPSC Code:
12352005
NACRES:
NA.21

grade

sublimed grade

Quality Level

100

Assay

≥99% (HPLC)

optical activity

[α]/D

loss

0.5% TGA, > 250 °C (weight loss)

mp

330-335 °C (lit.)

solubility

THF: soluble
chloroform: soluble
toluene: soluble

λmax

299 nm

fluorescence

λex 221-227 nm; λem ≥35000 nm (in 0.005g/l, Heptane)
λex 296-302 nm; λem ≥95000 nm (in 0.005g/l, Heptane)
λex 457-463 nm; λem ≥5000 nm (in 0.005g/l, Heptane)
λex 485-491 nm; λem ≥9000 nm (in 0.005g/l, Heptane)
λex 520-526 nm; λem ≥9000 nm (in 0.005g/l, Heptane)
λem 553 nm±10 nm in THF

Orbital energy

HOMO 5.4 eV 
LUMO 3.2 eV 

λ

in THF

UV absorption

λ: 299 nm±5 nm Amax

SMILES string

c1ccc(cc1)-c2c3ccccc3c(-c4ccccc4)c5c(-c6ccccc6)c7ccccc7c(-c8ccccc8)c25

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

InChI key

YYMBJDOZVAITBP-UHFFFAOYSA-N

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Application

5,6,11,12-Tetraphenylnaphthacene, also known as Rubrene, can be used in studies such as organic electronics and optoelectronics. Rubrene is widely used as an organic emitter material in OLED devices due to its high photoluminescence quantum yield and excellent electroluminescent properties. It emits intense red-orange light, making it suitable for red-emitting OLEDs. It exhibits excellent charge transport properties, allowing it to be used as an organic semiconducting material in OFET devices. Rubrene has been studied for potential applications in organic photovoltaic devices. It can be used in research areas in photovoltaics and sensors.
5,6,11,12-Tetraphenylnaphthacene, also known as Rubrene, is a solution-processable small molecular semiconductor. It is often used in chemiluminescence research and transition metal complex ligation. In OLED devices. it′s used as yellow fluorescent dopant.
Reagent for chemiluminescence research and for transition metal complex ligation.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Direct Comparison of Solution- and Vacuum-Processed Small Molecular Organic Light-Emitting Devices with a Mixed Single Layer
Wang, et al.
ACS Applied Materials & Interfaces, 3, 2496-2503 (2011)
Critical assessment of charge mobility extraction in FETs
Choi, Hyun Ho, et al.
Nature Materials, 17, 2-7 (2017)
Sarah Wieghold et al.
The journal of physical chemistry letters, 11(3), 601-607 (2020-01-03)
Recent advances in perovskite-sensitized photon upconversion via triplet-triplet annihilation (TTA) in rubrene have yielded several unanswered questions about the underlying mechanism and processes occurring at the interface. In particular, the near-infrared perovskite emission is not significantly quenched and a rapid
Quantum localization and delocalization of charge carriers in organic semiconducting crystals
Giannini, S. et al.
Nature Communications, 10, 3843-3843 (2019)

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