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Details

Stereochemistry ACHIRAL
Molecular Formula C26H20N2
Molecular Weight 360.4504
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BATHOCUPROINE

SMILES

CC1=CC(C2=CC=CC=C2)=C3C=CC4=C(N=C(C)C=C4C5=CC=CC=C5)C3=N1

InChI

InChIKey=STTGYIUESPWXOW-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C26H20N2
Molecular Weight 360.4504
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Bathocuproine is a promising organic material of a hole blocking layer in organic light-emitting diodes or an electron buffer layer in organic photovoltaic cells. When a thin layer of bathocuproine is inserted between the metal electrode and the organic layer of the organic semiconductor device, the electron injection/collection efficiency at the interface is significantly improved. As an organic electronic material bathocuproine useful as OLED electron transporter and hole blocker. Bathocuproine sulphonate acts as a specific chelator of monovalent copper Cu(I).

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Electroluminescence property of highly soluble Ir(III) complex utilized by various hole blocking layers in polymer light emitting diodes.
2010-05
3-Phenyl-pyridinium tetra-chlorido-aurate(III).
2010-02-27
Effect of secondary ligands' size on energy transfer and electroluminescent efficiencies for a series of europium(III) complexes, a density functional theory study.
2009-11-14
Dichlorido(6,6'-dimethyl-2,2'-bipyridine-κN,N')zinc(II).
2009-09-26
Dichlorido(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline-κN,N')mercury(II) acetonitrile hemisolvate.
2009-07-01
(2,9-Dimethyl-4,7-diphenyl-1,10-phen-anthroline-κN,N')bis-(thio-cyanato-κS)mercury(II).
2009-06-24
Equilibrium and ab initio computational studies on the adduct formation of 1,3-diketonato-lithium(I), -sodium(I) and -potassium(I) with 1,10-phenanthroline and its 2,9-dimethyl derivatives.
2009-06-15
2,9-Dimethyl-4,7-diphenyl-1,10-phenanthrolin-1-ium tetra-chloridoaurate(III).
2009-04-02
[The role of BCP in electroluminescence of multilayer organic light-emitting devices].
2009-03
[Spectral characteristics of white organic light-emitting devices based on a novel nitrile fluorescence dye].
2009-03
Improvement of viewing angle and pixel contrast ratio in green top-emitting organic light-emitting devices.
2008-06-09
Differential modulation of Alzheimer's disease amyloid beta-peptide accumulation by diverse classes of metal ligands.
2007-11-01
Oxidative modification of human ceruloplasmin by methylglyoxal: an in vitro study.
2006-05-31
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005-06
[The study of electroplex emission based on PVK/BCP].
2005-05
Design of rhenium(I) polypyridine biotin complexes as a new class of luminescent probes for avidin.
2005-03-21
A spectroscopic and computational study on the effects of methyl and phenyl substituted phenanthroline ligands on the electronic structure of Re(I) tricarbonyl complexes containing 2,6-dimethylphenylisocyanide.
2005-03-21
Copper-mediated oxidative DNA damage induced by eugenol: possible involvement of O-demethylation.
2004-12-31
Synthesis, characterization, photophysical properties, and biological labeling studies of a series of luminescent rhenium(I) polypyridine maleimide complexes.
2002-01-14
Chelation and intercalation: complementary properties in a compound for the treatment of Alzheimer's disease.
2000-06
Oxidative damage to cellular and isolated DNA by metabolites of a fungicide ortho-phenylphenol.
1999-05
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
In Tyrode buffer, S-nitrosocysteine (cysNO) (10 microM) broke down at a rate of 3.3 uM/min. Bathocuproine sulphonate (10 microM) reduced this to 0.5 uM/min.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:01:26 GMT 2025
Edited
by admin
on Mon Mar 31 19:01:26 GMT 2025
Record UNII
9THP2V94FX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BATHOCUPROINE
MI  
Common Name English
NSC-89195
Preferred Name English
BATHOCUPROINE [MI]
Common Name English
1,10-PHENANTHROLINE, 2,9-DIMETHYL-4,7-DIPHENYL-
Systematic Name English
BCP
Common Name English
2,9-DIMETHYL-4,7-DIPHENYL-1,10-PHENANTHROLINE
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID4063585
Created by admin on Mon Mar 31 19:01:26 GMT 2025 , Edited by admin on Mon Mar 31 19:01:26 GMT 2025
PRIMARY
PUBCHEM
65149
Created by admin on Mon Mar 31 19:01:26 GMT 2025 , Edited by admin on Mon Mar 31 19:01:26 GMT 2025
PRIMARY
MERCK INDEX
m2275
Created by admin on Mon Mar 31 19:01:26 GMT 2025 , Edited by admin on Mon Mar 31 19:01:26 GMT 2025
PRIMARY Merck Index
FDA UNII
9THP2V94FX
Created by admin on Mon Mar 31 19:01:26 GMT 2025 , Edited by admin on Mon Mar 31 19:01:26 GMT 2025
PRIMARY
NSC
89195
Created by admin on Mon Mar 31 19:01:26 GMT 2025 , Edited by admin on Mon Mar 31 19:01:26 GMT 2025
PRIMARY
MESH
C002478
Created by admin on Mon Mar 31 19:01:26 GMT 2025 , Edited by admin on Mon Mar 31 19:01:26 GMT 2025
PRIMARY
CAS
4733-39-5
Created by admin on Mon Mar 31 19:01:26 GMT 2025 , Edited by admin on Mon Mar 31 19:01:26 GMT 2025
PRIMARY
WIKIPEDIA
Bathocuproine
Created by admin on Mon Mar 31 19:01:26 GMT 2025 , Edited by admin on Mon Mar 31 19:01:26 GMT 2025
PRIMARY
ECHA (EC/EINECS)
225-240-5
Created by admin on Mon Mar 31 19:01:26 GMT 2025 , Edited by admin on Mon Mar 31 19:01:26 GMT 2025
PRIMARY