1499-10-1

Basic information

• Product Name: 9,10-Diphenylanthracene
• Synonyms: 9,10-diphenyl-anthracen;anthracene,9,10-diphenyl-;9,10-DIPHENYLANTHRACENE;9,10-DIPHENYLANTHRACEN 97%;9,10-DIPHENYLENEANTHRACENE OEKANAL, 250;Bis(2,4,6-Trichlorophenyl)EthanedioateTcpo;9,10-Diphenylanthracene(blue) (DPA);9,10-Diphenylanthracene, scintillation grade, 99+%
• CAS NO: 1499-10-1
• Molecular Formula: C₂₆H₁₈
• Molecular Weight: 330.42
• EINECS: 216-105-1
• Product Categories: Industrial/Fine Chemicals;Scintillators;Anthracenes;Electroluminescence;Functional Materials;Photoluminescent Materials > Light-Emitting Dopants and Fluorescent Dyes;Photonic and Optical Materials;DIO - DIZChemical Class;Alpha Sort;Analytical Standards;AromaticsVolatiles/ Semivolatiles;Chemical Class;D;DAlphabetic;Hydrocarbons;NeatsAnalytical Standards;PAHs;Arenes;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 1499-10-1.mol
• Article Data: 81

Chemical Properties

• Melting Point: 245-248 °C(lit.)
• Boiling Point: 485°C(lit.)
• Flash Point: 234.745 °C
• Appearance: Light yellow to beige/Fine Crystalline Powder
• Density: 1.1398 (estimate)
• Vapor Pressure: 1.59E-08mmHg at 25°C
• Refractive Index: 1.8430 (estimate)
• Storage Temp.: Store below +30°C.
• Water Solubility: INSOLUBLE
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 1914010
• CAS DataBase Reference: 9,10-Diphenylanthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-Diphenylanthracene(1499-10-1)
• EPA Substance Registry System: 9,10-Diphenylanthracene(1499-10-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37-26
• RIDADR: 2811
• WGK Germany: 3
• RTECS: SS6825000
• TSCA: Yes
• Hazardous Substances Data: 1499-10-1(Hazardous Substances Data)

Usage

Chemical Properties

slightly yellow powder

Uses

9,10-Diphenylanthracene acts as a sensitizer in chemiluminescence. It is used in light sticks in order to produce blue light. It is also useful in blue organic light-emitting diodes (OLEDs) and OLED-based displays. Further, it plays an important role in the preparation of 9,10-difluoro-9,10-diphenyl-9,10-dihydro-anthracene. In addition to this, it is used as an organic semiconductor.

Definition

ChEBI: 9,10-diphenylanthracene is a member of the class of anthracenes that is anthracene in which both of the hydrogens on the central ring are substituted by phenyl groups. It has a role as a fluorochrome and a photosensitizing agent.

Application

9,10-Diphenylanthracene is a polycyclic aromatic hydrocarbon and a useful organic semiconductor. 9,10-Diphenylanthracene is also a sensitiser in chemiluminescence. It has applications related to OLEDs and OLED-based displays.

General Description

9,10-Diphenylanthracene, an aromatic hydrocarbon, is a blue light emitting material that is used for the measurement of fluorescence quantum yields in dilute solutions. Its derivatives show potential candidature in organic light emitting diode (OLED) devices. It is also used as a fluorophore for the study of peroxyoxalate chemiluminescence (POCL).

Purification Methods

Crystallise the anthracene from acetic acid or xylene [Baumstark et al. J Org Chem 52 3308 1987]. [Beilstein 5 IV 2807.]

InChI:InChI=1/C26H18/c1-3-11-19(12-4-1)25-21-15-7-9-17-23(21)26(20-13-5-2-6-14-20)24-18-10-8-16-22(24)25/h1-18H

Synthetic route

9,10-Dibromoanthracene (523-27-3) + phenylboronic acid (98-80-6) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
With potassium phosphate; dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium(II) In toluene at 80℃; for 0.0833333h; Suzuki-Miyaura cross-coupling reaction; Air;	97%
With potassium carbonate In methanol at 80℃; for 0.5h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	97%
With potassium phosphate In ethanol at 80℃; for 2h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	97%

9,10-dichloroanthracene (605-48-1) + phenylmagnesium bromide (100-58-3) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride In 1,4-dioxane; diethyl ether at 20℃; for 24h; Kumada-Corriu cross-coupling reaction; Inert atmosphere;	95%
With methylmagnesium bromide; triethylamine; nickel dichloride In tetrahydrofuran; methanol; ethanol; toluene	80.4%
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran at 25 - 35℃; Inert atmosphere; Cooling with ice;	68.49%

9,10-diphenyl-9,10-epidioxyanthracene (15257-17-7) → 9,10-diphenylanthracene (1499-10-1) + oxygen (80937-33-3)

Conditions	Yield
In toluene for 24h;	A 95% B 37%

(9s,10s)-9,10-diphenyl-9,10-dihydro-9,10-epoxyanthracene (19061-38-2) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Sealed tube;	94%
With isopropylmagnesium bromide In tetrahydrofuran for 2h; Heating;	52%
With acetic acid; zinc
With zinc In acetic acid for 10h; Heating; Yield given;

9,10-dichloroanthracene (605-48-1) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
Pd(PPh3)4 In tetrahydrofuran; chlorobenzene	87.8%

anthranol (6318-17-8) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
With titanium tetrachloride; triethylamine In dichloromethane at 0 - 25℃; for 0.5h; Inert atmosphere;	82%
With formic acid; sodium formate
With acetic acid; potassium iodide

bromobenzene (108-86-1) + 9,10-Dibromoanthracene (523-27-3) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
Pd(PPh3)2Cl2 In tetrahydrofuran	81.7%
Pd(PPh3)2Cl2 In tetrahydrofuran	73.8%

9,10-Dibromoanthracene (523-27-3) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
Ni(dppe)Cl2 In tetrahydrofuran	81.7%
Ni(AcaC)2 In tetrahydrofuran	75.9%

Ni(PPh3)2Br2 + 9,10-dichloroanthracene (605-48-1) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
In tetrahydrofuran	81.4%

9,10-Dibromoanthracene (523-27-3) + phenylmagnesium bromide (100-58-3) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran at 25 - 35℃; Inert atmosphere; Cooling with ice;	75.45%

10-isocyano-9,10-diphenyl-4a,10-dihydroanthracene → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
In [D3]acetonitrile at 20℃; for 72h;	68%

magnesium bis(9,10-diphenylanthracenide) * 6 THF → 9,10-diphenylanthracene (1499-10-1) + C26H18Mg*3C4H8O (126615-80-3)

Conditions	Yield
In tetrahydrofuran at 60℃; for 4h;	A n/a B 65%

o-phthalic dicarboxaldehyde (643-79-8) + benzene (71-43-2) → anthracene (120-12-7) + 9-phenylanthracene (602-55-1) + 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
With boron trifluoride monohydrate at 20℃; for 16h; Sealed tube;	A 13% B 64% C 2%

1,3-diphenylisobenzofuran (5471-63-6) + 1,2-dibromobenzene (583-53-9) → 9,10-diphenylanthracene (1499-10-1) + 9,10-diphenyl-9,10-epidioxyanthracene (15257-17-7) + o-dibenzoylbenzene (1159-86-0)

Conditions	Yield
With dihydrogen peroxide; lithium diphenylphosphide In tetrahydrofuran Product distribution; Mechanism; multistep reaction; possible intermediate formation of dehydrobenzene;	A n/a B n/a C 60%

benzyne (462-80-6, 53356-60-8, 193469-78-2) + 2,5-diphenyl-6H-1,3,4-oxadiazin-6-one (63617-45-8) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
	60%

2-(trifluoromethyl)triphenylmethane (73475-39-5) → 9-phenylanthracene (602-55-1) + 9,10-diphenylanthracene (1499-10-1) + 9-fluoro-10-phenylanthracene (2022-42-6)

Conditions	Yield
With trifluorormethanesulfonic acid In chloroform at 0℃; for 4h; Inert atmosphere;	A n/a B n/a C 53%

phenyl benzyl ketone (451-40-1) + halobenzene → 9,10-diphenylanthracene (1499-10-1) + trans-1,2-diphenylbenzocyclobutenol

Conditions	Yield
Stage #1: phenyl benzyl ketone With tetramethylpiperidine; tert.-butyl lithium In tetrahydrofuran; hexane at -40℃; Stage #2: halobenzene In tetrahydrofuran; hexane at -40℃; for 5h;	A n/a B 52%

1-(α-bromobenzyl)-2-(α-bromo-α-phenylbenzyl)benzene (337309-40-7) → 9,10-diphenylanthracene (1499-10-1) + 2-(diphenylmethyl)benzophenone (102948-87-8)

Conditions	Yield
With tetraethylammonium bromide In N,N-dimethyl-formamide Electrolysis; Hg cathode; C anode; Ag reference electrode;	A 37% B 7%

diphenyl-9,10 diepoxy-4a,10:9,9a tetrahydro-4a,10.9,9a anthracene (80232-59-3) → 9,10-diphenylanthracene (1499-10-1) + 10-phenyl-10-hydroxy-9-anthracenone (5146-30-5) + diphenyl-4b,9b dihydro-4b,9b benzofuro<3,2-b>benzofurane (66927-73-9, 80232-58-2) + diphenyl-6,11 dihydro-6,11 epoxy-6,11-dibenzooxepine (36818-38-9)

Conditions	Yield
In diethyl ether at -37℃; for 24h; Irradiation;	A n/a B 31% C 35% D 10%

9,10-Dibromoanthracene (523-27-3) + benzene (71-43-2) → 9,10-diphenylanthracene (1499-10-1) + 9-bromo-10-phenylanthracene (23674-20-6)

Conditions	Yield
With 3-benzyl-1-(N-phenylcarbamoylmethyl)imidazolium chloride; potassium tert-butylate at 20 - 100℃; for 36h; Schlenk technique; Inert atmosphere; Green chemistry;	A 32% B 35%

2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) + 2,5-diphenyl-6H-1,3,4-oxadiazin-6-one (63617-45-8) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
With tetrabutylammonium triphenyldifluorosilicate In tetrahydrofuran at 20 - 60℃; for 24h; Inert atmosphere;	34.7%

9,10-diphenyl-9,10-epidioxyanthracene (15257-17-7) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
In benzene for 8h; Irradiation;	24%
Thermodynamic data; Product distribution; ΔH(excit.), ΔS(excit.), yield of 1O formation and isotonic effect in the thermolysis in various solvents;
Product distribution; Mechanism; thermolysis, magnetic isotope effect;
In 1,4-dioxane at 60.2℃; Thermodynamic data; Rate constant; ΔE<*>, log A, ΔH<*>, ΔS<*>; oxygen isotope effect; magnetic field effect; other solvents, temperatures;
In o-xylene at 80℃; Kinetics; Further Variations:; Temperatures;

1,3-diphenylisobenzofuran (5471-63-6) + (2-fluorophenyl)trimethylsilane (1842-26-8) → 9,10-diphenylanthracene (1499-10-1) + 9-(2-fluorophenyl)-10-phenylanthracene (134456-79-4) + 2-<(2-Fluorphenyl)phenylmethyl>benzophenon (134456-80-7) + o-dibenzoylbenzene (1159-86-0)

Conditions	Yield
With potassium tert-butylate In N,N,N,N,N,N-hexamethylphosphoric triamide at 0℃; for 1h;	A n/a B n/a C 21% D n/a

9,10-dichloro-9,10-diphenyl-9,10-dihydro-anthracene (6486-01-7) → 9,10-diphenylanthracene (1499-10-1) + 10-phenyl-10-hydroxy-9-anthracenone (5146-30-5) + C52H38O4 (113882-03-4)

Conditions	Yield
With potassium ozonate In dichloromethane; Dichlorodifluoromethane at -50℃; for 1h;	A 10% B n/a C n/a

9,10-Dibromoanthracene (523-27-3) + phenylboronic acid (98-80-6) → biphenyl (92-52-4) + 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
With dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; triethylamine In water at 20℃; for 24h; Suzuki-Miyaura Coupling; Green chemistry;	A 10% B 10%

formic acid (64-18-6) + anthranol (6318-17-8) + sodium formate (141-53-7) → 9,10-diphenylanthracene (1499-10-1)

formic acid (64-18-6) + Methyl-(10-hydroxy-9.10-diphenyl-9.10-dihydro-anthryl-(9))-aether (859336-12-2) → 9,10-diphenylanthracene (1499-10-1)

benzophenone (119-61-9) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
With calcium
With calcium hydride

1,1-Diphenylmethanol (91-01-0) → 9,10-diphenylanthracene (1499-10-1)

Conditions	Yield
With calcium hydride

9,10-diphenylanthracene (1499-10-1) → 9,10-diphenyl-9,10-epidioxyanthracene (15257-17-7)

Conditions	Yield
With oxygen; methylene blue In dichloromethane at -78 - 20℃; Irradiation;	100%
With CaO2*2H2O2 In tetrahydrofuran at 50℃; for 3h;	98%
With oxygen; methylene blue In chloroform for 3h; UV-irradiation;	90%

9,10-diphenylanthracene (1499-10-1) → cis,trans-9,10-diphenyl-9,10-dihydroanthracene (803-58-7)

Conditions	Yield
With hydrogen iodide; acetic acid for 120h; Heating;	99%
With potassium hydroxide semihydrate; phosphorus; water In dimethyl sulfoxide at 120℃; for 3h; Temperature; Inert atmosphere; regioselective reaction;	74%
With Dicalcium Nitride Electride In tetrahydrofuran; isopropyl alcohol at 65℃; for 24h; Birch Reduction; Inert atmosphere;	50%
With sodium amalgam; ethanol
Multi-step reaction with 2 steps 1: Li / liquid ammonia / -60 °C / reduction by alkali metal 2: tetrahydrofuran / -40 °C / quenching with parent compound View Scheme

9,10-diphenylanthracene (1499-10-1) → 9,10-diphenyl-9,10-dihydro-9,10-epidioxyanthracene (15257-17-7)

Conditions	Yield
With oxygen In toluene at 20℃; under 760.051 Torr; for 7.5h; Irradiation;	99%
With dihydrogen peroxide In dichloromethane at 20℃; for 3h;	61%
With hematoporphyrin In tetrahydrofuran; ethanol at 17℃; Irradiation; Yield given;

1-(2,6-difluorophenyl)pyrrole-2,5-dione + 9,10-diphenylanthracene (1499-10-1) → (3aR)-2-(2,6-difluorophenyl)-5,10-diphenyl-3a,4,11,11a-tetrahydro-1H-4,11-ethenonaphtho[2,3-f]isoindole-1,3(2H)-dione (1617526-43-8)

Conditions	Yield
With aluminum (III) chloride In chloroform at 20℃; for 1h; Temperature; Solvent; Diels-Alder Cycloaddition; stereoselective reaction;	98%
at 140℃; for 120h; Diels-Alder Cycloaddition; stereoselective reaction;	92%

9,10-diphenylanthracene (1499-10-1) + C27H18F2O4 → C53H36F2O4

Conditions	Yield
In toluene at 100℃; for 8h; Diels-Alder Cycloaddition; Green chemistry; regioselective reaction;	93%

9,10-diphenylanthracene (1499-10-1) + C27H18Cl2O4 → C53H36Cl2O4

Conditions	Yield
In toluene at 100℃; for 8h; Diels-Alder Cycloaddition; Green chemistry; regioselective reaction;	89%

9,10-diphenylanthracene (1499-10-1) + C31H26Cl2O4 (1577232-64-4) → C57H44Cl2O4

Conditions	Yield
In toluene at 100℃; for 8h; Diels-Alder Cycloaddition; Green chemistry; regioselective reaction;	87%

9,10-diphenylanthracene (1499-10-1) → C26H20O2

Conditions	Yield
With dihydrogen peroxide; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 0℃;	85%

9,10-diphenylanthracene (1499-10-1) → 9,10-diphenyl-1,2,3,4,5,6,7,8-octahydroanthracene (342794-86-9)

Conditions	Yield
With tetrahydrofuran; methylmagnesium bromide; hydrogen; cobalt acetylacetonate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride at 0 - 60℃; under 60006 Torr; for 48h; Autoclave; regioselective reaction;	83%

9,10-diphenylanthracene (1499-10-1) + dimethyl 2,2-bis(5-phenylpenta-2,4-diyn-1-yl)malonate (1384480-00-5) → C53H38O4

Conditions	Yield
In toluene at 100℃; for 8h; Diels-Alder Cycloaddition; Green chemistry; regioselective reaction;	83%

9,10-diphenylanthracene (1499-10-1) + C33H32O4 → C59H50O4

Conditions	Yield
In toluene at 100℃; for 8h; Diels-Alder Cycloaddition; Green chemistry; regioselective reaction;	83%

diethyl 2,2-bis(5-phenylpenta-2,4-diyn-1-yl)malonate (1068614-44-7) + 9,10-diphenylanthracene (1499-10-1) → C55H42O4

Conditions	Yield
In toluene at 100℃; for 8h; Diels-Alder Cycloaddition; Green chemistry; regioselective reaction;	82%

9,10-diphenylanthracene (1499-10-1) + C31H28O4 (1577232-58-6) → C57H46O4

Conditions	Yield
In toluene at 100℃; for 8h; Diels-Alder Cycloaddition; Green chemistry; regioselective reaction;	82%

9,10-diphenylanthracene (1499-10-1) + dimethyl 2,2-bis(5-(p-tolyl)penta-2,4-diyn-1-yl)malonate → C55H42O4

Conditions	Yield
In toluene at 100℃; for 8h; Diels-Alder Cycloaddition; Green chemistry; regioselective reaction;	81%

9,10-diphenylanthracene (1499-10-1) + C31H28O4 → C57H46O4

Conditions	Yield
In toluene at 100℃; for 8h; Diels-Alder Cycloaddition; Green chemistry; regioselective reaction;	81%

9,10-diphenylanthracene (1499-10-1) + C31H28O4 (1577232-61-1) → C57H46O4

Conditions	Yield
In toluene at 100℃; for 8h; Diels-Alder Cycloaddition; Green chemistry; regioselective reaction;	81%

9,10-diphenylanthracene (1499-10-1) + C35H36O4 → C61H54O4

Conditions	Yield
In toluene at 100℃; for 8h; Diels-Alder Cycloaddition; Green chemistry; regioselective reaction;	81%

9,10-diphenylanthracene (1499-10-1) → 9,10-Difluoro-9,10-diphenyl-9,10-dihydro-anthracene (38399-73-4)

Conditions	Yield
With tetrabutyl ammonium fluoride In acetonitrile electrolysis at 0.95 V vs. Ag/Ag+;	80%

9,10-diphenylanthracene (1499-10-1) → rubicene (197-61-5)

Conditions	Yield
With trifluorormethanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 0℃; for 0.166667h; Scholl Reaction; Inert atmosphere;	80%

Upstream product

• 109-69-3 n-Butyl chloride 
• 78-86-4 s-butyl chloride 
• 6486-01-7 9,10-dichloro-9,10-diphenyl-9,10-dihydro-anthracene 
• 57-13-6 urea 
• 36204-66-7 trans-9,10-dihydroxy-9,10-diphenyl-9,10-dihydroanthracene 
• 64-19-7 acetic acid 
• 84-65-1 9,10-phenanthrenequinone 
• 859336-12-2 Methyl-(10-hydroxy-9.10-diphenyl-9.10-dihydro-anthryl-⁽⁹⁾)-aether 
• 337309-39-4 1-(α-hydroxybenzyl)-2-(α-hydroxy-α-phenylbenzyl)benzene 
• 102948-87-8 2-(diphenylmethyl)benzophenone 
• 408313-84-8 2,2-dioxo-1,1,3-triphenyl-1,3-dihydro-2λ⁶-benzo[c]thiophene 
• 96179-18-9 10-methoxy-9,10-diphenyl-9,10-dihydro-[9]anthryl hydroperoxide 
• 6318-17-8 anthranol 
• 803-58-7 cis,trans-9,10-diphenyl-9,10-dihydroanthracene 

Downstream Products

• 97151-76-3 9,10-Diethoxy-9,10-dihydro-9,10-diphenylanthracen 
• 2348-55-2 sec-Butyl-Radikal 
• 2492-36-6 n-butyl radical 
• 3744-21-6 2,2-dimethyl-propyl 
• 71880-21-2 2,2-Dimethyl-hex-5-enyl-Radikal 
• 123676-18-6 12-(p-nitrobenzoyl)-1,3-dichloro-6,11-diphenyl-11,12-dihydro-6,11<1',2'>-benzeno-6H-dibenz<1,4>oxazocine 
• 38399-73-4 9,10-Difluoro-9,10-diphenyl-9,10-dihydro-anthracene 
• 1499-10-1 9,10-diphenylanthracene dication 
• 113882-02-3 C₂₆H₁₈O₃ 
• 15257-17-7 9,10-diphenyl-9,10-dihydro-9,10-epidioxyanthracene 
• 2819-03-6 1-adamantyl radical 
• 68525-40-6 C₁₁H₁₅ 
• 128252-08-4 CCDC-756597 
• 128252-03-9 9.10t-dimethoxy-9r.10c-diphenyl-9.10-dihydro-anthracene 

Relevant articles and documents

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The ortho, meta, and para isomers of 9,10-dipyridylanthracene 1 have been synthesized and converted into their endoperoxides 1-O2 upon oxidation with singlet oxygen. The kinetics of this reaction can be controlled by the substitution pattern an

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Kinetic and equilibrium parameters of [4+2] cycloaddition reaction of 2,6-dimethylnaphthalene with 4-phenyl-1,2,4-triazoline-3,5-dione

Kinetic parameters of forward and retro Diels-Alder reactions between 2,6-dimethylnaphthalene and 4-phenyl-1,2,4-triazolinedione were determined, as well as the equilibrium parameters of the reaction in 1,2-dichloroethane.

Palladium supported hybrid cellulose-aluminum oxide composite for Suzuki-Miyaura cross coupling reaction

A cellulose-aluminum oxide composite was prepared and modified with organo-functional groups by reacting with the coupling reagent (CH 3O)3Si(CH2)3NH2 through Al-O-Si bonds. The amino groups confined in the composite were found to be efficient for palladium entrapment, leading to a highly active and reusable heterogeneous catalyst (Pd@Al2O3-CELL) for Suzuki-Miyaura cross coupling reaction in water and H2O/DMF (8:2) mixture at 80 °C. Copyright

Radical cations of twisted acenes: Chiroptical properties and spin delocalization

We introduce the first series of enantiopure twistacene radical cations, which form reversibly upon chemical or electrochemical oxidation. Their vis-NIR chiroptical properties (Cotton effect and anisotropy factor) increase systematically with the backbone twist. The hyperfine constants observed by EPR demonstrate significant spin delocalization even for large backbone twist angles.

Low temperature Kumada-Corriu cross-coupling of polychlorinated acene derivatives and a synthesis of sterically demanding acenes

Conditions for low-temperature Kumada-Corriu cross-coupling of polychlorinated acenes with Grignard reagents are reported. Our work was motivated by a search for cross-coupling reactions effective in the synthesis of functionalized linear acenes for organic materials applications. Treatment of polychlorinated acenes with the PEPPSI-IPr catalyst and MeMgBr undergo 6-8 concurrent coupling reactions to yield products such as octamethylnaphthalene, which is distorted out of planarity due to the steric interaction between the methyl groups. More sterically demanding Grignard reagents such as PhMgBr coupled cleanly with 9,10-dichloroanthracene to provide products such as 9,10-diphenylanthracene, a blue OLED component, in excellent yield.

State-Selective Photochemistry of Singlet Oxygen Precursors: Kinetics and Wavelength Dependence of the Photodissociation of Anthracene Endoperoxides

The photochemical behavior of the two isomeric endoperoxides (9,10-PMO2 and 1,4-PMO2) of 1,4-dimethyl-9,10-diphenylanthracene was found to differ in their kinetics and reaction efficiencies.Consistent with the work of Rigaudy et al. and Brauer et al. on a related endoperoxide we find that the generation of 1O2 is wavelength dependent, occuring from upper excited singlet states of the endoperoxide, whereas bond cleavage of the O-O endoperoxide bond occurs principally from the lowest excited singlet and triplet states.Results of picosecond kinetics and absolute quantum yield measurements are discussed in terms of various concerted and nonconcerted mechanisms for the formation of 1O2 and the anthracene fragment.

The improvement of π-conjugation by the lateral benzene of anthracene and naphthalene

The 1,4-diarylnaphthalenes, 1,4-diarylanthracenes, and 9,10-diarylanthracenes containing the different side arenes, including phenyl, 2-thienyl, and 2-furyl groups, were synthesized to study the influence of structures on π-conjugation. According to photophysics and computation, the smaller dihedral angles and the lateral benzene of anthracene would increase the π-conjugation in some cases. Compared to 1,4-diarylnaphthalenes, 1,4-di(thien-2-yl)anthracene, 1,4-di(fur-2-yl)anthracene, and 9,10-di(fur-2-yl)anthracene displayed better π-conjugation in both of the ground and fluorescing excited states, but 9,10-di(thien-2-yl)anthracene only showed better π-conjugation in the fluorescing excited state.

Synthesis of symmetrical and unsymmetrical 9,10-diarylanthracene derivatives via bis-Suzuki-Miyaura cross-coupling reaction

Synthesis of various 9,10-diarylanthracene derivatives via bis-Suzuki-Miyaura cross-coupling reaction as a key step is described. Availability of the 9,10-dithienylanthracenes derivatives where the thiophene unit is present in the molecule (e. g. 11, 12, 14) may provide an easy access to novel polymer and/or dendrimer preparation. In addition, we have synthesized unsymmetrical 9,10-diarylanthracene derivatives 20-25 by the Suzuki-Miyaura cross-coupling reaction, which are difficult to prepare by other transition metal-catalyzed cross-coupling reactions.

Synthesis of N-Heterocyclic Carbine Silver(I) and Palladium(II) Complexes with Acylated Piperazine Linker and Catalytic Activity in Three Types of C—C Coupling Reactions

Two bis-imidazolium salts LH2·Cl2 and LH2·(PF6)2 with acylated piperazine linker and two N-heterocyclic carbene (NHC) silver(I) and palladium(II) complexes [L2Ag2](PF6)2 (1) and [L2Pd2Cl4] (2) were prepared. The crystal structures of LH2·Cl2 and 1 were confirmed by X-ray analysis. In 1, one 26-membered macrometallocycle was generated through two silver(I) ions and two bidentate ligands L. The catalytic activity of 2 was investigated in Sonogashira, Heck-Mizoroki and Suzuki-Miyaura reactions. The results displayed that these C—C coupling reactions can be smoothly carried out under the catalysis of 2.

Modular synthesis of unsymmetrical doubly-ring-fused benzene derivatives based on a sequential ring construction strategy using oxadiazinones as a platform molecule

An efficient benzene ring construction method using oxadiazinones as a platform molecule has been developed. Sequential reactions of oxadiazinones with cycloalkynes and arynes afforded partially reduced polyaromatics. This method enables facile preparation of various unsymmetrical doubly-ring-fused benzene derivatives including multisubstituted tetrahydroanthracenes and anthracenes.