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

Base Information

• Chemical Name: 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline
• CAS No.: 4733-39-5
• Molecular Formula: C26H20N2
• Molecular Weight: 360.458
• Hs Code.: 29339990
• European Community (EC) Number: 225-240-5
• NSC Number: 89195
• UNII: 9THP2V94FX
• DSSTox Substance ID: DTXSID4063585
• Nikkaji Number: J8.767J
• Wikipedia: Bathocuproine
• Wikidata: Q27273191
• ChEMBL ID: CHEMBL220061
• Mol file: 4733-39-5.mol

Synonyms:2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline;bathocuproine;bathocuproine sulfite (1:2)

Chemical Property of 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 7.38E-11mmHg at 25°C
• Melting Point: 279-283 ºC
• Refractive Index: 1.686
• Boiling Point: 531.9 ºC at 760 mmHg
• PKA: 5.88±0.30(Predicted)
• Flash Point: 231 ºC
• PSA: 25.78000
• Density: 1.173 g/cm³
• LogP: 6.73380
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Benzene (Slightly, Heated), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• Water Solubility.: Soluble in methanol (36mg/100ml), ethanol, 2-propanol, bezene, and acetone. Partly miscible in water.
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 360.162648646
• Heavy Atom Count: 28
• Complexity: 461

Purity/Quality:

>99% ^*data from raw suppliers

Bathocuproine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 24/25-36-26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: CC1=CC(=C2C=CC3=C(C=C(N=C3C2=N1)C)C4=CC=CC=C4)C5=CC=CC=C5
• Description: Bathocuproine (BCP) 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.?BCP is one of the most popular hole-blocking layer materials that is used in organic electronics, including perovskite solar cells.
• Uses: It is used as a reagent for the determination of copper. It acts as an exciton blocking barrier which prohibits excitons diffusion process towards the Al electrode otherwise being quenched. It is the most commonly used buffer layer between acceptor and cathode layer. Bathocuproine is used as a reagent for the determination of copper. It acts as an exciton blocking barrier which prohibits excitons diffusion process towards the Al electrode otherwise being quenched. It is the most commonly used buffer layer between acceptor and cathode layer.

Technology Process of 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline

There total 11 articles about 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4,7-dichloro-2,9-dimethyl-1,10-phenanthroline + phenylboronic acid (98-80-6) → Bathocuproine (4733-39-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; water; for 24h; Reflux; Inert atmosphere;

DOI:10.1039/c6dt02474b

Reference yield:

C36H25MnN6O3 → 5-Phenyl-1H-tetrazole (18039-42-4,3999-10-8) + carbon monoxide (201230-82-2) + Bathocuproine (4733-39-5)

Guidance literature:

In dichloromethane; UV-irradiation;

DOI:10.1002/ejic.201900987

Reference yield:

1,2-diamino-benzene (95-54-5) → Bathocuproine (4733-39-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 0.25 h / Reflux

1.2: 2 h / Reflux

2.1: diphenylether / 0.67 h / 240 - 260 °C

3.1: trichlorophosphate / 3.5 h / 90 °C / Inert atmosphere

4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 24 h / Reflux; Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; trichlorophosphate; In tetrahydrofuran; diphenylether; water; 4.1: |Suzuki-Miyaura Coupling;

DOI:10.1039/c6dt02474b

upstream raw materials:

2-methyl-8-nitro-4-phenyl-quinoline

1-phenylbut-2-en-1-one

2-nitro-aniline

1,2-diamino-benzene

Downstream raw materials:

{Cu(bcn)2}ClO₄

bis(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)copper(I) hexafluorophosphate

(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)palladium(II) acetate

Pd(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)Cl₂

Refernces

• 1、 Edwards, Alyn C.,Wagner, Christoph,Geist, Andreas,Burton, Neil A.,Sharrad, Clint A.,Adams, Ralph W.,Pritchard, Robin G.,Panak, Petra J.,Whitehead, Roger C.,Harwood, Laurence M.. "Exploring electronic effects on the partitioning of actinides(III) from lanthanides(III) using functionalised bis-triazinyl phenanthroline ligands". . p. 18102 - 18112. Retrieved 2016/11/25.