PRODUCTS

BATHOCUPROINE

Bathocuproine is a versatile phenanthroline derivative widely used in copper analysis, coordination chemistry, and advanced optoelectronic applications.
Bathocuproine's strong metal-chelating ability and effective hole-blocking performance make it valuable in both analytical methods and electronic devices.
Bathocuproine is especially important in OLEDs, organic photovoltaics, and perovskite solar cells where it helps improve interfacial charge management.

CAS Number: 4733-39-5
EC Number: 225-240-5
Molecular Formula: C26H20N2
Molecular Weight: 360.45 g/mol

Synonyms: Bathocuproine, 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline, 4733-39-5, 1,10-Phenanthroline, 2,9-dimethyl-4,7-diphenyl-, 9THP2V94FX, DTXSID4063585, NSC-89195, RefChem:561106, DTXCID9040556, 225-240-5, Bathocuproin, MFCD00004972, 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline;Bathocuproin;2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline;2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline [BCP], 2,9-dimethyl-4,7-diphenylpyridino[3,2-h]quinoline, 4,7-Diphenyl-2,9-dimethyl-1,10-phenanthroline, NSC89195, Bathocuproine, 96%, BATHOCUPROINE [MI], Oprea1_173365, SCHEMBL36914, BIDD:GT0563, CHEMBL220061, orb2815697, SCHEMBL29351092, SCHEMBL29356702, STTGYIUESPWXOW-UHFFFAOYSA-, 2,7-diphenyl-1,10-phenanthroline, CS-D1200, 1, 2,9-dimethyl-4,7-diphenyl-, SBB008863, AKOS005145736, Bathocuproine (purified by sublimation), DS-4182, FB52492, AC-24458, SY010658, DB-050427, D0711, EU-0070645, NS00031681, ST50308524, 2,9-dimethyl-4,7-diphenyl-1,1-phenanthroline, O10635, 2,9-dimethyl-4,7-diphenyl-1,10-phenantroline, 2.9-Dimethyl-4.7-diphenyl-1.10-phenanthroline, 2,9,-dimethyl-4,7-diphenyl-1,10-phenanthroline, F235890, T202009, 2,9-dimethyl-4,7-di(phenyl)-1,10-phenanthroline, doi:10.14272/STTGYIUESPWXOW-UHFFFAOYSA-N.1, 2, 9-Dimethyl-4, 7-diphenyl-1, 10-phenanthroline, 4, 7-Diphenyl-2, 9-dimethyl-1, 10-phenanthroline, Q27273191, Bathocuproine, sublimed grade, 99.99% trace metals basis, 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline; Bathocuproine, 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (purified by sublimation), InChI=1/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, 4,4′-(2,9-Dimethyl-1,10-phenanthrolin-4,7-diyl)dibenzolsulfonsäure, , 4,4′-(2,9-Dimethyl-1,10-phenanthroline-4,7-diyl)dibenzenesulfonic acid, , Acide 4,4′-(2,9-diméthyl-1,10-phénanthroline-4,7-diyl)dibenzènesulfonique, bathocuproine disulfonic acid, Benzenesulfonic acid, 4,4′-(2,9-dimethyl-1,10-phenanthroline-4,7-diyl)bis-, 31037-51-1, 4-[2,9-DIMETHYL-7-(4-SULFOPHENYL)-1,10-PHENANTHROLIN-4-YL]BENZENE-1-SULFONIC ACID, 73348-75-1, Bathocuproine disulfonate, bathocuproine sulfonate, BATHOCUPROINE-4,4′-DISULFONIC ACID, Bathocuproinedisulphonic acid

Bathocuproine is an organic compound with the formula (C6H5)2(CH3)2C12H4N2.
Bathocuproine is related to 1,10-phenanthroline by the placement of two methyl groups and two phenyl groups in the 2,9 and 4,7 positions, respectively.

Like 1,10-phenanthroline, bathocuproine is a bidentate chelating ligand.
The two methyl groups flank the nitrogen centers, such that bathocuproine is a bulky ligand.
Bathocuproine forms a monomeric 1:1 complex with nickel(II) chloride, whereas the less bulky parent phenanthroline forms a 2:1 complex.

Bathocuproine was first prepared by Case and Brennan in the early 1950s is a pale yellow solid that is soluble in polar organic solvents.

Organic photovoltaic cells (OPVCs) are considered to be promising devices because of their mechanical flexibility, ease of fabrication and potential for low-cost production.
For small-molecule OPVCs the most-common material to use between the acceptor, here C60, and the top electrode, Al, is 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, also known as bathocuproine.

Indeed, the insertion of Bathocuproine results in an enhanced power-conversion efficiency (PCE).
The improved power-conversion efficiency has been attributed to an increased exciton harvesting in the active layer.
As Bathocuproine is a wide-band-gap material it acts as an exciton-blocking barrier (EBL) that prohibits excitons diffusing towards the Al electrode where they would otherwise be quenched.

Bathocuproine is used as a reagent for the determination of copper.
Bathocuproine acts as an exciton blocking barrier which prohibits excitons diffusion process towards the Al electrode otherwise being quenched.
Bathocuproine is the most commonly used buffer layer between acceptor and cathode layer.

Bathocuproine has been a valuable synthetic compound in scientific research for several decades.
This cationic dye finds extensive applications in various scientific studies, including fluorescence microscopy and histochemical staining.

Bathocuproine plays a role in biochemical and physiological investigations, primarily due to its remarkable affinity for proteins and other molecules.
Bathocuproine is frequently employed as a fluorescent marker in cell biology and histology.

This paper aims to delve into the synthesis method, scientific research applications, mechanism of action, biochemical and physiological effects, advantages, limitations, and future directions concerning Bathocuproine research.
Bathocuproine boasts a wide array of applications within the scientific research realm.

Bathocuproine is utilized as a fluorescent marker in cell biology and histology due to its strong binding capacity with proteins and other molecules.
Fluorescence microscopy benefits from the high affinity of Bathocuproine for DNA and RNA.

Moreover, Bathocuproine has been employed as a histochemical stain to identify the presence of proteins, lipids, and carbohydrates.
The binding mechanism of Bathocuproine involves a cation-exchange process.

This cationic dye readily binds to negatively charged molecules like proteins and DNA, forming a stable covalent bond.
This exceptional covalent bond formation enables Bathocuproine to effectively bind to proteins and other molecules, thus serving as useful as a fluorescent marker.

Bathocuproine is a copper(I)-specific chelator.
Bathocuprone binds Cu⁺ tightly and is widely used in biochemical assays of copper and to modulate copper-dependent processes in cell culture.
In vitro, bathocuproine sulfonate (a water-soluble analog) abolishes copper-mediated toxicity in cultured cells and alters cysteine/cystine metabolism by inhibiting copper-catalyzed oxidation, and when paired with cysteine it can enhance growth of certain cells or Plasmodium under specific conditions, consistent with copper chelation effects at low micromolar to millimolar concentrations.

Bathocuproine is the most popular electron transport material due to its wide-band-gap and high electron affinity.
A thin layer of Bathocuproine inserted between a metal cathode and an electron transport layer improves the performances of organic light emitting diodes and organic photovoltaic cells (including perovskite solar cells) significantly.

Bathocuproine has a large ionization energy of 6.5 eV, which is the highest occupied molecular orbital derived-level (HOMO level) with respect to the vacuum level and corresponds to the hole transport level.
Thus, the Bathocuproine layer was initially intended to block the exciton and hole diffusion from the electron transport layer to the cathode.

Bathocuproine is an aromatic nitrogen-containing heterocyclic compound derived from 1,10-phenanthroline.
Bathocuproine is widely used as a copper-chelating reagent and as a functional organic material in electronic and optoelectronic applications.
Bathocuproine is especially important as a hole-blocking and interfacial layer material in OLEDs, organic solar cells, and perovskite solar cells.

Bathocuproine is a highly versatile compound known for its exceptional ability to chelate metal ions, particularly copper.
This property makes it invaluable in various applications, including analytical chemistry, where it is used as a reagent for the detection and quantification of copper in different matrices.

Bathocuproine's strong affinity for copper ions allows for precise measurements, making it a preferred choice among researchers and industry professionals.
Additionally, Bathocuproine is utilized in the field of photochemistry, where it serves as a stabilizing agent in organic light-emitting diodes (OLEDs) and other optoelectronic devices, enhancing their performance and longevity.

Moreover, Bathocuproine's unique structure contributes to its effectiveness in various applications, including its role in the development of sensors and catalysts.
Bathocuproine's ability to form stable complexes with metal ions not only aids in analytical applications but also opens avenues for innovative research in materials science and nanotechnology.
With its broad range of uses and significant advantages over similar compounds, Bathocuproine stands out as a crucial tool for professionals seeking reliable and efficient solutions in their work.

Applications of Bathocuproine:
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.

Bathocuproine is a wide-band-gap material and has a high electron affinity.
When it is embedded into organic electronic devices, bathocuproine acts as an exciton-blocking barrier which prohibits exciton diffusion process towards the Al electrode otherwise being quenched.

One of the most commonly used buffer layer between acceptor and cathode layers is bathocuproine.
The introduction of the buffer layer can greatly improve the PCE of polymer organic solar cells.

Bathocuproine is one of the most popular hole-blocking layer materials that is used in organic electronics, including perovskite solar cells.
Bathocuproine was demonstrated that a BCP buffer layer reduces nonradiative recombination of excitons at the C60 –Al interface.
Bathocuproine's most important function is to establish an Ohmic contact between the C60 film and the Al electrode in photovoltaic devices.

Uses of Bathocuproine:
Bathocuproine is used as a reagent for the determination of copper.
Bathocuproine acts as an exciton blocking barrier which prohibits excitons diffusion process towards the Al electrode otherwise being quenched.
Bathocuproine is the most commonly used buffer layer between acceptor and cathode layer.

Bathocuproine can be used as an electron-modifying layer or as an interlayer between ETLs (electron transport layers) in calcite solar cells, and it can be prepared by spin-coating deposition or vacuum thermal evaporation.
The addition of Bathocuproine enhances the energy conversion efficiency of organic photovoltaic cells.

Bathocuproine is used as a selective chelating reagent for copper ions in analytical and coordination chemistry.
Bathocuproine is used as a hole-blocking material in organic light-emitting diodes (OLEDs).

Bathocuproine is used as an interfacial layer in organic photovoltaic and perovskite solar cells.
Bathocuproine is used to improve charge transport and reduce electron-hole recombination in optoelectronic devices.

Bathocuproine is used in spectrophotometric methods for the detection and determination of copper.
Bathocuproine is used in research involving metal-ion complexation, semiconductor interfaces, and organic electronic materials.

Advantages of Bathocuproine:
Bathocuproine provides strong and selective complexation with copper ions, making it useful in analytical and coordination chemistry.
Bathocuproine offers effective hole-blocking properties that can improve charge separation and reduce recombination in optoelectronic devices.

Bathocuproine is compatible with thin-film electronic applications and can enhance interfacial performance in OLEDs, organic solar cells, and perovskite solar cells.
Bathocuproine has a well-defined aromatic structure that contributes to good electronic and optical stability in research applications.

Bathocuproine can be used in sensitive spectrophotometric methods for copper determination.
Bathocuproine is versatile across analytical chemistry, materials science, and organic electronics.

Synthesis of Bathocuproine:
Bathocuproine can be synthesized through the condensation and cyclization of o-phenylenediamine with an α,β-unsaturated ketone such as 4-phenyl-3-buten-2-one under acidic conditions.
The reaction forms the substituted 1,10-phenanthroline ring system, followed by oxidation and aromatization to produce 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline.
Classical procedures are related to the Skraup or Doebner–von Miller phenanthroline synthesis, while newer methods use optimized acid-catalyzed one-step routes to improve efficiency and product yield.

Stability and Reactivity of Bathocuproine:

Chemical Stability:
Stable under normal and recommended storage conditions.

Reactivity:
No hazardous reactions are expected under normal handling and processing conditions.

Conditions to Avoid:
Avoid excessive heat and contact with incompatible materials.

Incompatible Materials:
Strong oxidizing agents.

Hazardous Decomposition Products:
Thermal decomposition or combustion may produce carbon oxides, nitrogen oxides and irritating gases or vapors.

Handling and Storage of Bathocuproine:

Safe Handling:
Handle in a well-ventilated area.
Avoid dust formation, inhalation, ingestion and contact with skin or eyes.

Storage Conditions:
Keep the container tightly closed in a cool, dry and well-ventilated place.
Keep away from incompatible materials.

First Aid Measures of Bathocuproine:

Inhalation:
Move the affected person to fresh air.
Obtain medical attention if symptoms persist.

Skin Contact:
Wash thoroughly with plenty of water and soap.
Remove contaminated clothing and seek medical attention if irritation develops.

Eye Contact:
Rinse immediately with plenty of water for at least 15 minutes.
Obtain medical attention if irritation persists.

Ingestion:
Rinse mouth with water.
Do not give anything by mouth to an unconscious person.
Seek medical attention.

Firefighting Measures of Bathocuproine:

Suitable Extinguishing Media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Specific Hazards:
Combustion or thermal decomposition may release carbon oxides, nitrogen oxides and irritating fumes.

Protective Equipment:
Firefighters should wear self-contained breathing apparatus and suitable protective clothing.

Accidental Release Measures of Bathocuproine:

Personal Precautions:
Avoid dust formation and inhalation.
Ensure adequate ventilation and wear appropriate personal protective equipment.

Environmental Precautions:
Prevent the material from entering drains, surface water or the environment.

Cleanup Methods:
Carefully sweep or collect spilled material without generating dust and place it in a suitable closed container for disposal.

Exposure Controls/Personal Protective of Bathocuproine:

Engineering Controls:
Provide adequate ventilation and local exhaust where dust may be generated.

Eye Protection:
Wear safety glasses or protective goggles.

Hand Protection:
Wear suitable chemical-resistant protective gloves.

Skin Protection:
Wear appropriate protective clothing.

Respiratory Protection:
Respiratory protection is generally not required under normal conditions; use a suitable particulate respirator when dust exposure is significant or ventilation is inadequate.

General Hygiene:
Wash hands thoroughly after handling and before eating, drinking or smoking.

Identifiers of Bathocuproine:
CAS Number: 4733-39-5
Molecular Formula: C26H20N2
Molecular Weight: 360.45 g/mol
PubChem CID: 65149
IUPAC Name: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
InChI Key: STTGYIUESPWXOW-UHFFFAOYSA-N

CAS: 4733-39-5
IUPAC Name: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
Molecular Formula: C26H20N2
InChI Key: STTGYIUESPWXOW-UHFFFAOYSA-N
SMILES: CC1=CC(C2=CC=CC=C2)=C2C=CC3=C(C=C(C)N=C3C2=N1)C1=CC=CC=C1
Molecular Weight (g/mol): 360.46
Synonym: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline

Product Number: B2694
Purity / Analysis Method : >99.0%(T)(HPLC)
Molecular Formula / Molecular Weight: C26H20N2 = 360.46
Physical State (20 deg.C): Solid
Storage Temperature : Room Temperature (Recommended in a cool and dark place, <15°C)
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Air Sensitive
Packaging and Container : 1G-Glass Bottle with Plastic Insert (View image)
CAS RN: 4733-39-5
Reaxys Registry Number: 306714
PubChem Substance ID: 87558362
SDBS (AIST Spectral DB): 11056
MDL Number:
MFCD00004972

CAS No.: 4733-39-5
Chemical Name: Bathocuproine
CBNumber: CB2299411
Molecular Formula: C26H20N2
Molecular Weight: 360.45
MDL Number: MFCD00004972

CAS Number: 4733-39-5
ChEMBL: ChEMBL220061
ChemSpider: 58658
ECHA InfoCard: 100.022.945
EC Number: 225-240-5
PubChem CID: 65149
UNII: 9THP2V94FX
CompTox Dashboard (EPA): DTXSID4063585
InChI: 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
Key: STTGYIUESPWXOW-UHFFFAOYSA-N
SMILES: CC1=NC2=C(C=CC3=C2N=C(C=C3C4=CC=CC=C4)C)C(=C1)C5=CC=CC=C5

Empirical Formula (Hill Notation): C26H20N2
CAS Number: 4733-39-5
Molecular Weight: 360.45
UNSPSC Code: 12352103
NACRES: NA.23
PubChem Substance ID: 24848482
EC Number: 225-240-5
Beilstein/REAXYS Number: 306714
MDL number: MFCD00004972

Properties of Bathocuproine:
Chemical formula: C26H20N2
Molar mass: 360.460 g·mol−1
Appearance: Pale yellow solid
Melting point: 283 °C (541 °F; 556 K)
Solubility in water: organic solvents

assay: 96%
form: powder
manufacturer/tradename: ECACC
sustainability: Greener Alternative Product
mp: 279-283 °C (lit.)
λmax: ~280 nm in methanol
orbital energy: HOMO 7 eV , LUMO 3.5 eV
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

Molecular Weight: 360.4 g/mol
XLogP3-AA: 6.5
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 2
Exact Mass: 360.162648646 Da
Monoisotopic Mass: 360.162648646 Da
Topological Polar Surface Area: 25.8 Å²
Heavy Atom Count: 28
Complexity: 461
Isotope Atom Count: 0
Computed by PubChem
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Melting point: 279-283 °C(lit.)
Boiling point: 482.47°C (rough estimate)
Density: 1.2408 (rough estimate)
refractive index: 1.7620 (estimate)
storage temp.: Sealed in dry,Room Temperature
solubility: Benzene (Slightly, Heated), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
form: Powder
pka: 5.88±0.30(Predicted)
color: Yellow
Water Solubility: Soluble in methanol (36mg/100ml), ethanol, 2-propanol, bezene, and acetone. Partly miscible in water.
λmax: 277 nm
BRN: 306714
InChI: 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
InChIKey: STTGYIUESPWXOW-UHFFFAOYSA-N
SMILES: N1C2C(=CC=C3C=2N=C(C)C=C3C2=CC=CC=C2)C(C2=CC=CC=C2)=CC=1C

Specifications of Bathocuproine:
Appearance (Color): White to yellow or pale cream to pale brown
Form: Crystals or powder or crystalline powder
Assay (Non-aqueous acid-base Titration): ≥97.5 to ≤102.5% (non-U.S. sourced material)
Assay from Supplier's CofA: ≥97.5% (U.S. sourced material)
Comment: Material sourced in the U.S. and in other countries
Identification (FTIR): Conforms (non-U.S. sourced material)
GC/MS Analysis: Conforms (U.S. sourced material)

Names of Bathocuproine:

Preferred IUPAC name:
2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline

Other names:
2,9-Dimethyl-4,7-diaphenyl-1,10-phenanthroline
2,9-Dimethyl-4,7-diphenylphenanthroline
4,7-Diphenyl-2,9-dimethyl-1,10-phenanthroline
BCP