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140910

Sigma-Aldrich

Bathocuproine

greener alternative

96%

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:
24848482
NACRES:
NA.23

Assay

96%

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.)

λmax

~280 nm in methanol

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

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

Bathocuproine can be used as an electron modificationlayer or interlayer between ETL(electron transport layer) in perovskite solarcells, which can be fabricated using the spin-coating deposition method or thevacuum thermal evaporation method. The addition of bathocuproine enhances thepower conversion efficiency of organic photovoltaic cells.

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF4996V
WXBF4329V
WXBF3183V
WXBF2860V
WXBF3592V

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What solvents can be used to dissolve Product 140910, Bathocuproine?

    This product can be dissolved in 5% pyridine to yield a dark yellow solution. It is also soluble in methanol (36 mg/100ml), isoamyl alcohol (18 mg/100 ml), dioxane (100 mg/ml), 95% ethanol (50 mg/ml) and nitrobenzene.

  5. What is the maximum absorbance wavelength for Product 140910, Bathocuproine?

    The ?max is at approximately 280 nm in methanol.

  6. What are the possible applications for Product 140910, Bathocuproine?

    It can be used for Cu(I) detection, range 0.1-10 ppm, as it is a Cu(I)-specific colorimetric reagent. It is also an organic electron transporting material.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Electromodulation of photoluminescence in vacuum-evaporated films of bathocuproine
Misnik, M., Falkowski, K., Mroz, W., & Stampor, W.
Chemical Physics, 410, 45-54 (2013)
Structural templating as a route to improved photovoltaic performance in copper phthalocyanine/fullerene (C 60) heterojunctions
Sullivan, P., et al.
Applied Physics Letters, 91(23), 233114-233114 (2007)
Development of air stable polymer solar cells using an inverted gold on top anode structure.
Sahin, Yucel, et al.
Thin Solid Films, 476(2), 340-343 (2005)
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)
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
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