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699152

Sigma-Aldrich

Bathocuproine

greener alternative

sublimed grade, 99.99% trace metals basis

Synonym(s):

2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline, BCP

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About This Item

Empirical Formula (Hill Notation):
C26H20N2
CAS Number:
4733-39-5
Molecular Weight:
360.45
Beilstein:
306714
EC Number:
225-240-5
MDL number:
MFCD00004972
UNSPSC Code:
12352103
PubChem Substance ID:
329762113
NACRES:
NA.23

grade

sublimed grade

Assay

99.99% trace metals basis

form

powder

greener alternative product characteristics

Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

279-283 °C (lit.)
285 °C (DSC)

λmax

277 nm

fluorescence

λem 386 nm in THF

Orbital energy

HOMO 7 eV 
LUMO 3.5 eV 

OLED Device Performance

ITO/CuPc/NPD/TCTA/mCP:Firpic (6%)/BCP/LiF/Al

  • Color: blue
  • Max. EQE: 4.2 %

ITO/NPD/CBP:Ir(ppy)3/BCP/Alq3/Mg:Al
  • Color: green
  • Max. Luminance: 100000 Cd/m2
  • Max. EQE: 8 %
  • Turn-On Voltage: 4.3 V

ITO/NPD/TCTA/BCPO:Ir(piq)3 (7-8%)/BCP/Alq3/LiF/Al
  • Color: red
  • Max. Luminance: 24529 Cd/m2
  • Max. EQE: 17 %
  • Turn-On Voltage: 2.7 V

ITO/NPD/TCTA/BCPO:Ir(ppy)3 (7-8%)/BCP/Alq3/LiF/Al
  • Color: green
  • Max. Luminance: 207839 Cd/m2
  • Max. EQE: 21.6 %
  • Turn-On Voltage: 2.1 V

greener alternative category

, Enabling

SMILES string

Cc1cc(-c2ccccc2)c3ccc4c(cc(C)nc4c3n1)-c5ccccc5

InChI

1S/C26H20N2/c1-17-15-23(19-9-5-3-6-10-19)21-13-14-22-24(20-11-7-4-8-12-20)16-18(2)28-26(22)25(21)27-17/h3-16H,1-2H3

InChI key

STTGYIUESPWXOW-UHFFFAOYSA-N

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General description

TGA/DSC Lot specific scans available upon request
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product belongs to Enabling category of greener alternatives thus aligns with "Design for energy efficency". Electron transport organic materials have the chemical functionality to transport electrons and are used as electron transport layer in OLED devices. Click here for more information.

Application

Organic electronic material useful as OLED electron transporter and hole blocker.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H413

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Douglas Ganini et al.
Free radical biology & medicine, 53(7), 1514-1521 (2012-07-25)
Ceruloplasmin (ferroxidase) is a copper-binding protein known to promote Fe(2+) oxidation in plasma of mammals. In addition to its classical ferroxidase activity, ceruloplasmin is known to catalyze the oxidation of various substrates, such as amines and catechols. Assays based on
Kazutaka Hirakawa et al.
Free radical research, 38(5), 439-447 (2004-08-06)
Titanium dioxide (TiO2) is a potential photosensitizer for photodynamic therapy. In this study, the mechanism of DNA damage catalyzed by photo-irradiated TiO2 was examined using [32P]-5'-end-labeled DNA fragments obtained from human genes. Photo-irradiated TiO2 (anatase and rutile) caused DNA cleavage
Takuya Iwamoto et al.
Pharmaceutical research, 25(3), 598-604 (2007-08-22)
It has been reported that dacarbazine (DTIC) is photogenotoxic. The purpose of this study is to clarify the mechanism of photogenotoxicity induced by DTIC. We examined DNA damage induced by UVA-irradiated DTIC using 32P-5'-end-labeled DNA fragments obtained from human genes.
Zachary J Peters et al.
Reproductive toxicology (Elmsford, N.Y.), 23(4), 513-520 (2007-03-21)
The trophoblast cell line, JEG-3, was used to study the cytotoxicity of phenanthrene, 9,10-phenanthrenequinone (PHEQ), anthracene, and 9,10-anthracenedione alone and with copper. The endpoints were the capacity of cultures to reduce alamar Blue (AB), a measure of energy metabolism, and
Brian V Popp et al.
Journal of the American Chemical Society, 126(45), 14832-14842 (2004-11-13)
The mechanism of olefin substitution at palladium(0) has been studied, and the results provide unique insights into the fundamental reactivity of electron-rich late transition metals. A systematic series of bathocuproine-palladium(0) complexes bearing trans-beta-nitrostyrene ligands (ns(X) = X-C(6)H(4)CH=CHNO(2); X = OCH(3)
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