1662-01-7

Basic information

• Product Name: Bathophenanthroline
• Synonyms: 4,7-Diphenyl-1,1-phenanthroline;4,7-DIPHENYL-1,10-PHENANTHROLINE;BATHOPHENANTHROLINE;TIMTEC-BB SBB008862;1,10-bathophenanthroline;10-Phenanthroline,4,7-diphenyl-1;4,7-Diphenyl-1,10-diazaphenanthrene;4,7-Diphenyl-1,10-phenanthroli
• CAS NO: 1662-01-7
• Molecular Formula: C₂₄H₁₆N₂
• Molecular Weight: 332.4
• EINECS: 216-767-1
• Product Categories: Achiral Nitrogen;Py-N;Analytical Chemistry;Chelating Reagents;Electroluminescence;Functional Materials;Highly Purified Reagents;Other Categories;Phenanthrolines;Refined Products by Sublimation;White crystalline powder;White crystalline powder;oled materials;organic amine
• Mol File: 1662-01-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 218-220 °C(lit.)
• Boiling Point: 459.52°C (rough estimate)
• Flash Point: 242.111 °C
• Appearance: White to yellow to pinkish/Crystalline Powder, Crystals or Crystalline Mass
• Density: 1.2047 (rough estimate)
• Vapor Pressure: 2.63E-11mmHg at 25°C
• Refractive Index: 1.7620 (estimate)
• Storage Temp.: Store at +15°C to +25°C.
• Solubility: Soluble in organic solvents. Slightly soluble in acidic aqueous
• PKA: 4.83±0.10(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 261048
• CAS DataBase Reference: Bathophenanthroline(CAS DataBase Reference)
• NIST Chemistry Reference: Bathophenanthroline(1662-01-7)
• EPA Substance Registry System: Bathophenanthroline(1662-01-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: SF8427000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 1662-01-7(Hazardous Substances Data)

Usage

Classification

Hole-blocking layer (HBL) materials , Electron injection layer (EIL) materials, OLEDS, Organic photovoltaics, Perovskite solar cells.

Applications

BPhen is widely used as a hole-blocking or exciton-blocking layer due to its wide energy gap and high ionisation potential. The phenanthroline unit is small, rigid, and planar, with extended π-electrons and short hopping lengths that facilitate electron mobility. The electron mobility of BPhen is about 5 × 10-4 cm2 V-1 s-1, which is about two orders of magnitude higher than that of Alq3. When doped with lithium, BPhen:Li is an excellent electron-transport material, and is often used as an electron-injection layer to enable ohmic contact to any electrode -- without the need to consider the work function alignments.

Reactions

Bidentate ligand and reagent for determination of iron. Ligand used in the copper-catalyzed protodecarboxylation of aromatic carboxylic acids.

Description

BPhen is widely used as a hole-blocking or exciton-blocking layer due to its wide energy gap and high ionisation potential.

Chemical Properties

white to faintly yellow crystalline powder

Uses

Different sources of media describe the Uses of 1662-01-7 differently. You can refer to the following data:
1. Bathophenanthroline is widely used for determination of iron in serum and urine by colorimtetry. It acts as buffer layer to improve the efficiency of organic photovoltaic cells. It is very useful as a scavenger reagent, for the removal of traces of iron and copper from reagent solutions, which is used in the trace metal determination. Iron bathophenanthroline complex is involved as a redox mediating agent for imaging surface immobilized deoxyribonucleic acid (DNA) by using Scanning Electrochemical Microscopy (SECM).
2. Bathophenanthroline was used in an ultra-sensitive and selective nonextractive quenchofluorimetric method, in order to determine palladium (II) at μg/l Levels. It may also be used as the buffer layer to improve the performance of organic photovoltaic cells.

Definition

ChEBI: A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two phenyl substituents at positions 4 and 7.

General Description

This product has been enhanced for catalysis.

InChI:InChI=1/C24H16N2/c1-3-7-17(8-4-1)19-13-15-25-23-21(19)11-12-22-20(14-16-26-24(22)23)18-9-5-2-6-10-18/h1-16H

Synthetic route

3-chloropropiophenone (936-59-4) + 1,2-diamino-benzene (95-54-5) → bathophenanthroline (1662-01-7)

Conditions	Yield
With hydrogenchloride; hydrogen iodide In water at 100℃; for 0.333333h; Reagent/catalyst; Temperature;	76.4%

4-phenyl-8-aminoquinoline (55484-55-4) + 3-chloropropiophenone (936-59-4) → bathophenanthroline (1662-01-7)

Conditions	Yield
With phosphoric acid; orthoarsenic acid

3-chloropropiophenone (936-59-4) → bathophenanthroline (1662-01-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: arsenic acid; aqueous sulfuric acid 2: SnCl2+2 H2O; ethanol 3: syrupy H3PO4; H3aso4 View Scheme

4-phenyl-8-nitroquinoline (25771-65-7) → bathophenanthroline (1662-01-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: SnCl2+2 H2O; ethanol 2: syrupy H3PO4; H3aso4 View Scheme

2-nitro-aniline (88-74-4) → bathophenanthroline (1662-01-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: arsenic acid; aqueous sulfuric acid 2: SnCl2+2 H2O; ethanol 3: syrupy H3PO4; H3aso4 View Scheme

[Co(4,7-diphenyl-1,10-phenanthroline)2(diflunisal)][hexafluorophosphate] → bathophenanthroline (1662-01-7) + 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid (22494-42-4)

Conditions	Yield
In aq. phosphate buffer at 37℃; for 24h; Time;

bis-(dimethyl(phenyl)silylmethyl)(cycloocta-1,5-diene)platinum(II) + bathophenanthroline (1662-01-7) → bis-(dimethyl(phenyl)silylmethyl)(4,7-diphenyl-1,10-phenanthroline)platinum(II)

Conditions	Yield
In toluene Ar atmosphere; stirring (60°C, 28 d); removal of excess of ligand on washing with aq. FeSO4, concn., pptn. on addn. of hexane; elem. anal.;	99%

bis(triphenylphosphino)copper(I) nitrate (14494-93-0, 23751-62-4, 106678-35-7) + bathophenanthroline (1662-01-7) + triphenylphosphine (603-35-0) → (4,7-diphenyl-1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate (1262033-35-1)

Conditions	Yield
In chloroform at 20℃; for 1h; Schlenk technique;	99%

bathophenanthroline (1662-01-7) → 2-methyl-4,7-diphenyl-1,10-phenanthroline

Conditions	Yield
With methyllithium In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere;	99%

MoO2Br2(NCCH3)2 + bathophenanthroline (1662-01-7) → ((C6H5)2C12H6N2)MoO2(Br)2

Conditions	Yield
In tetrahydrofuran N2; stirred for 1 h; cncd., pptd. (ether), ppt. washed (diethyl ether), dried (vac.); elem. anal.;	98%

bathophenanthroline (1662-01-7) + chromium(III) chloride (10025-73-7) → [(4,7-diphenyl-1,10-phenanthroline)2CrCl2]Cl (1242583-98-7)

Conditions	Yield
With Zn In ethanol solid anhyd. CrCl3 was added to a suspn. of phenanthroline-compound in abs. ethanol, a trace amount of zinc dust was added, the mixt. was heatedto reflux for 1 h; filtered, rotary evapd.;	98%

bathophenanthroline (1662-01-7) + [(η5-C5H4CH2C6H4Br-4)Mo(CO)2(NCMe)2][BF4] → [(η5-C5H4CH2C6H4Br-4)Mo(CO)2(4,7-Ph2-phen)][BF4]

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;	98%

silver tetrafluoroborate (14104-20-2) + bathophenanthroline (1662-01-7) + 1,3-bis-(diphenylphosphino)propane (6737-42-4) → [Ag2(4,7-diphenyl-1,10-phenanthroline)2(μ-1,3-bis(diphenylphosphino)propane)](BF4)2

Conditions	Yield
Stage #1: silver tetrafluoroborate; 1,3-bis-(diphenylphosphino)propane In methanol; dichloromethane for 1h; Inert atmosphere; Schlenk technique; Stage #2: bathophenanthroline In methanol; dichloromethane for 1h; Inert atmosphere; Schlenk technique;	97%

dichloro(benzene)ruthenium(II) dimer (37366-09-9) + bathophenanthroline (1662-01-7) → [(BZ)(Ph2phen)RuCl]Cl

Conditions	Yield
In methanol for 3.25h; Inert atmosphere; Reflux;	97%
In water for 0.25h; Sonication; Green chemistry;

bathophenanthroline (1662-01-7) + [(η5-C5H4CH2C6H4F-4)Mo(CO)2(NCMe)2][BF4] → [(η5-C5H4CH2C6H4F-4)Mo(CO)2(4,7-Ph2-phen)][BF4]

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;	97%

bathophenanthroline (1662-01-7) + diethylzinc (557-20-0) → C28H26N2Zn

Conditions	Yield
for 1h; Inert atmosphere; Schlenk technique; Glovebox;	97%

bis(pentafluorophenyl)(1,5-cyclooctadiene)platinum(II) + bathophenanthroline (1662-01-7) → (4,7-diphenylphenanthroline)Pt(C6F5)2 (852954-53-1)

Conditions	Yield
recrystn. and subl.;	96%

copper(II) choride dihydrate + bathophenanthroline (1662-01-7) + (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) → Cu(4,7-diphenyl-1,10-phenanthroline)(naproxen)2

Conditions	Yield
Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: copper(II) choride dihydrate; bathophenanthroline In methanol at 50℃; for 20h;	96%

tetrakis(actonitrile)copper(I) hexafluorophosphate (64443-05-6) + bathophenanthroline (1662-01-7) + bis[2-(diphenylphosphino)phenyl] ether (166330-10-5) → C60H44CuN2OP2(1+)*F6P(1-) (1421057-29-5)

Conditions	Yield
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; bis[2-(diphenylphosphino)phenyl] ether In dichloromethane Schlenk technique; Reflux; Stage #2: bathophenanthroline In dichloromethane at 20℃; Schlenk technique; Reflux;	95%

dichlorobis(dimethylsulfoxide)platinum(II) (30729-25-0, 25794-47-2, 15274-33-6, 22840-91-1, 75992-73-3, 14568-13-9) + bathophenanthroline (1662-01-7) → dichlorido(4,7-diphenyl-1,10-phenanthroline)platinum(II) (35273-41-7)

Conditions	Yield
In methanol for 3h; Reflux;	95%

copper(II) choride dihydrate + diethyl ether (60-29-7) + bathophenanthroline (1662-01-7) + (S,S)-1,2-diaminocyclohexane (21436-03-3) + potassium perchlorate → [copper(II)((1S,2S)-diaminocyclohexane)(4,7-diphenyl-1,10-phenanthroline)](perchlorate)2*0.5(C4H10O)

Conditions	Yield
In ethanol; water at 60℃; for 3.5h;	94%

(tetra-n-butylammonium)2[Mo3S7Cl6] + bathophenanthroline (1662-01-7) → Mo3S7Cl4(4,7-diphenyl-1,10-phenanthroline)

Conditions	Yield
In dichloromethane at 20℃; for 6.5h; Reflux;	94%

bathophenanthroline (1662-01-7) + methyllithium (917-54-4) → 2-methyl-4,7-diphenyl-1,10-phenanthroline

Conditions	Yield
In diethyl ether; toluene at 0 - 20℃; for 1h; Schlenk technique; Inert atmosphere;	94%
In diethyl ether; toluene at 0℃; for 0.5h;	63%
In diethyl ether; toluene at 0℃; for 0.5h; Inert atmosphere; Schlenk technique;	55%

uranyl nirate hexahydrate + bathophenanthroline (1662-01-7) → [UVIO2(NO3)2(4,7-diphenyl-1,10-phenanthroline)]

Conditions	Yield
In acetonitrile at 20℃; for 0.5h;	94%

tetrakis(acetonitrile)copper(I)tetrafluoroborate + bathophenanthroline (1662-01-7) + bis(diphenylphosphino)acetylene (5112-95-8) + benzene (71-43-2) → C100H72Cu2N4P4(2+)*2BF4(1-)*C6H6

Conditions	Yield
Stage #1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; bis(diphenylphosphino)acetylene In dichloromethane; acetonitrile for 0.5h; Inert atmosphere; Stage #2: bathophenanthroline In dichloromethane; acetonitrile for 1h; Inert atmosphere; Stage #3: benzene In diethyl ether at -100.16℃;	94%

tetrakis(acetonitrile)copper(I)tetrafluoroborate + bathophenanthroline (1662-01-7) + bis(diphenylphosphino)acetylene (5112-95-8) → [Cu2(μ-dppa)2(bathophenanthroline)2](BF4)2

Conditions	Yield
Stage #1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; bis(diphenylphosphino)acetylene In dichloromethane; acetonitrile for 0.5h; Inert atmosphere; Stage #2: bathophenanthroline In dichloromethane; acetonitrile for 1h; Inert atmosphere;	94%

bathophenanthroline (1662-01-7) + palladium diacetate (3375-31-3) → (4,7-diphenyl-1,10-phenanthroline)palladium(II) acetate (95246-09-6)

Conditions	Yield
In dichloromethane; toluene at 20℃; Inert atmosphere;	93%
In dichloromethane; toluene at 20℃; Inert atmosphere;	93%
With CH3COOH In acetone (Pd(MeCOO)2) is dissolved in acetone at room temp., after 30 min soln. is filtd. and a few drops of glacial acetic acid are added, the ligand is added as a solid to the soln.; ppt. is filtd., washed with cold acetone and dried in vac., elem. anal.;	70%

bathophenanthroline (1662-01-7) + 1,3-dibromo-propane (109-64-8) → 2Br(1-)*C27H22N2(2+)

Conditions	Yield
at 130℃; for 6h; Inert atmosphere;	93%
In nitrobenzene Menschutkin reaction;
With oxygen for 0.5h; Reflux;
In toluene Reflux;

ethanol (64-17-5) + Eu2(Piv)6(HPiv)6*HPiv + bathophenanthroline (1662-01-7) → [(4,7-diphenyl-1,10-phenanthroline)2Eu2(piv)6]*2EtOH

Conditions	Yield
In ethanol EtOH added to 4,7-Ph2-1,10-phen and Eu complex, heated at 80°C; filtered, concd.(vac.) at room temp., kept at 20°C for 24 h, washed (cold EtOH), dried (air), elem. anal.;	93%
With air at 80℃; Schlenk technique;	53%

[{η5-C5H4(C5F4N)}Mo(CO)2(NCMe)2][BF4] + bathophenanthroline (1662-01-7) → [{η5-C5H4(C5F4N)}Mo(CO)2(4,7-diphenyl-1,10-phenanthroline)][BF4]

Conditions	Yield
In dichloromethane at 20℃; for 16h;	93%

bathophenanthroline (1662-01-7) + [(η5-C5H4CH2C6H4Cl-4)Mo(CO)2(NCMe)2][BF4] → [(η5-C5H4CH2C6H4Cl-4)Mo(CO)2(4,7-Ph2-phen)][BF4]

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;	93%

+ 5,7-dihydroxy-2-phenyl-chromen-4-one (480-40-0) + bathophenanthroline (1662-01-7) → C39H25CuN2O4(1+)*ClO4(1-)

Conditions	Yield
Stage #1: copper(II) perchlorate hexahydrate; 5,7-dihydroxy-2-phenyl-chromen-4-one In methanol at 20℃; for 0.5h; Stage #2: bathophenanthroline In methanol at 20℃; for 2h;	93%

cis-bis{(trimethylsilyl)methyl}(1,5-cyclooctadiene)platinum(II) (36223-69-5) + bathophenanthroline (1662-01-7) → bis(trimethylsilylmethyl)(4,7-diphenyl-1,10-phenanthroline)platinum(II)

Conditions	Yield
In toluene under Ar, heated to 60°C for 14 days; extn. (aq. ferrous sulphate soln.), organic phase concd., addn. of n-hexane, cooled, washed with hexane; elem. anal.;	92%

Upstream product

• 55484-55-4 8-Amino-4-phenylquinoline 
• 936-59-4 3-chloropropiophenone 
• 88-74-4 2-nitro-aniline 
• 5394-23-0 4,7-dichloro-1,10-phenanthroline 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 95-54-5 1,2-diamino-benzene 
• 25771-65-7 8-nitro-4-phenylquinoline 

Downstream Products

• 69178-81-0 [Cr(4,7-diphenyl-1,10-phenanthroline)3](ClO₄)3 
• 35273-41-7 dichlorido(4,7-diphenyl-1,10-phenanthroline)platinum(II) 
• 106548-41-8 [(4,7-diphenyl-1,10-phenanthroline)₂RuCl₂] 
• 36309-88-3 ruthenium(II)-tris-4,7-diphenyl-1,10-phenanthroline dichloride 
• 83005-95-2 W(CO)4(4,7-diphenyl-1,10-phenanthroline) 
• 120782-63-0 {Rh(1,5-cyclooctadiene)(4,7-diphenyl-1,10-phenanthroline)}{Rh(1,5-cyclooctadiene)Br₂} 
• 120782-60-7 {Rh(1,5-cyclooctadiene)(4,7-diphenyl-1,10-phenanthroline)}Br 
• 75213-31-9 tris(4,7-diphenyl-1,10-phenanthroline)ruthenium(II) perchlorate 

Related news

Aggregation of non-amphiphilic Bathophenanthroline (cas 1662-01-7) in the restricted geometry of Langmuir–Blodgett films with two different matrices09/25/2019

The behavior of binary mixed Langmuir monolayers from the mixture of non-amphiphilic bathophenanthroline (BPH) and behenic acid (BA)/poly(methyl methacrylate) (PMMA) spread on aqueous subphase was investigated on the basis of the analysis of surface pressure–average area per molecule (π–A) is...detailed

Short communicationEffects of a Bathophenanthroline (cas 1662-01-7) exciton blocking layer on thermal annealing-free bulk heterojunction solar cells09/24/2019

The effects of bathophenanthroline (Bphen) as an exciton blocking layer (EBL) on annealing-free bulk heterojunction solar cells were investigate. A nonannealed donor–acceptor conjugated polymer was employed as the donor to ensure the simplicity of device fabrication and good reproducibility of ...detailed

Synthesis, structure, theoretical studies and luminescent properties of a ternary erbium(III) complex with acetylacetone and Bathophenanthroline (cas 1662-01-7) ligands09/10/2019

A novel erbium(III) complex with acetylacetone (Hacac) and bathophenanthroline (4,7-diphenyl-1,10-phenanthroline, bath) ligands, formulated as [Er(acac)3(bath)], has been characterized by elemental analysis, X-ray diffraction, thermogravimetric analysis, Fourier transform infrared spectroscopy, ...detailed

Synthesis and photoluminescence properties of asymmetrical europium(III) complexes involving carbazole, phenanthroline and Bathophenanthroline (cas 1662-01-7) units09/09/2019

Three novel europium complexes, Eu(CCHPD)3Phen = Tris[1-(9H-carbazol-9-yl)-3-[(6-(9H- carbazol-9-yl)hexoxy)-phenyl]-1,3-dione](1,10-phenanthroline) europium(III), Eu(CCHPD)3Bath = Tris[1-(9H-carbazol-9-yl)-3-[(6-(9H-carbazol-9-yl)hexoxy)-phenyl]-1,3-dione](bathophenanthroline) europium(III) and ...detailed

Short communicationEffect of charge carrier behaviours in LiF-doped Bathophenanthroline (cas 1662-01-7) (LiF:Bphen) on the performance of organic light-emitting diodes09/08/2019

Charge carrier behaviours of LiF-doped bathophenanthroline (LiF:Bphen) were investigated by single carrier devices: electron-only and hole-only devices. The results indicate that LiF doped with Bphen has dual roles: increasing current density due to enhanced electron injection and transport; dec...detailed

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