20302-14-1

Basic information

• Product Name: 9,9-Diphenylfluorene
• Synonyms: 9,9-Diphenylfluorene;9H-Fluorene, 9,9-diphenyl-
• CAS NO: 20302-14-1
• Molecular Formula: C₂₅H₁₈
• Molecular Weight: 318.41042
• Mol File: 20302-14-1.mol

Chemical Properties

• Melting Point: 224.0 to 228.0 °C
• Boiling Point: 438.9 °C at 760 mmHg
• Flash Point: 216 °C
• Appearance: /
• Density: 1.157 g/cm³
• Vapor Pressure: 1.72E-07mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Toluene
• CAS DataBase Reference: 9,9-Diphenylfluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,9-Diphenylfluorene(20302-14-1)
• EPA Substance Registry System: 9,9-Diphenylfluorene(20302-14-1)

Safety Data

• Hazardous Substances Data: 20302-14-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronic Devices:
9,9-Diphenylfluorene is utilized as a key component in organic light-emitting diodes (OLEDs) for its high thermal stability and efficient electron transport properties, which contribute to the performance and longevity of these devices.
Used in Organic Photovoltaics:
In the field of organic photovoltaics, 9,9-Diphenylfluorene is employed for its potential to enhance the efficiency of solar cells by improving charge transport and light absorption.
Used in Field-Effect Transistors:
9,9-Diphenylfluorene serves as a material in field-effect transistors, where its electron transport properties are leveraged to achieve better device performance and stability.
Used as a Laser Dye:
Owing to its strong blue emission, 9,9-Diphenylfluorene is used as a laser dye in various applications that require specific wavelength emissions, such as in scientific research and material processing.
Used in Fluorescence Research:
9,9-Diphenylfluorene is applied in fluorescence research due to its fluorescence properties, which are valuable for studying molecular interactions, imaging, and sensing applications across different scientific disciplines.

InChI:InChI=1/C25H18/c1-3-11-19(12-4-1)25(20-13-5-2-6-14-20)23-17-9-7-15-21(23)22-16-8-10-18-24(22)25/h1-18H

Upstream product

• 6326-62-1 (biphenyl-2-yl)(diphenyl)methanol 
• 64-19-7 acetic acid 
• 462-06-6 fluorobenzene 
• 591-51-5 phenyllithium 
• 108-86-1 bromobenzene 
• 60-29-7 diethyl ether 
• 86-73-7 9H-fluorene 
• 76-84-6 triphenylmethyl alcohol 
• 789-24-2 9-Phenylfluorene 
• 71-43-2 benzene 
• 25603-67-2 9-phenyl-fluoren-9-ol 
• 341-02-6 trityl tetrafluoroborate 
• 119-61-9 benzophenone 
• 82214-69-5 2-biphenylmagnesium bromide 

Downstream Products

• 2396-01-2 phenyl radical 
• 612-94-2 2-phenylnaphthalene 
• 605-02-7 1-phenylnaphthalene 
• 71-43-2 benzene 
• 1196694-11-7 N-(naphthalen-1-yl)-9,9-diphenyl-9H-fluoren-2-amine 
• 186259-63-2 2,7-dibromo-9,9-diphenyl-9H-fluorene 
• 2108145-19-1 2-nitro-9,9-diphenylfluorene 

Relevant articles and documents

Synthesis of Heterocycle-Containing 9,9-Diarylfluorenes Using Superelectrophiles

A superacid-promoted method for the synthesis of 9,9-diarylfluorenes is described. The chemistry involves cyclizations and arylations with biphenyl-substituted heterocyclic ketones and a mechanism is proposed involving superelectrophilic intermediates. The key reactive intermediates-dicationic and trication fluorenyl cations have been observed by low-temperature NMR and the mechanism has been further studied using DFT calculations.

The Argon Laser-Jet Initiated, Multiple-Photon (Reluctant), Electrocyclic Ring Opening of 10,10-Diphenyl-9-(10H)-phenanthrenone: A Carbene and Biradical Modeling Study.

While 10,10-diphenyl-9-(10H)-phenanthrenone (1) is inert under conventional irradiation conditions, it undergoes decarbonylation under high-intensity argon laser-jet conditions to form 9,9-diphenylfluorene (3) and the cycloheptatriene 4.Molecular modeling studies indicate that 3 arises from collapse of the singlet carbene 15 and the triene 4 from the triplet carbene 35.

Compound constituting a hole transfer layer and an electron transfer layer of an organic light emitting diode or a method for producing the same

The present invention relates to a compound constituting a hole transport layer and an electron transport layer of an organic light emitting diode, or a method for manufacturing the same. According to the present invention, it is possible to provide a plurality of compounds having excellent yields and excellent purity constituting the hole transport layer and the electron transport layer. An object of the present invention is to provide the compound constituting the hole transport layer and the electron transport layer of the organic light emitting diode, or the method for manufacturing the same.(AA) HPLC analysis result of a final productCOPYRIGHT KIPO 2020

Synthesis of spirocyclic diarylfluorenes by one-pot twofold SNAr reactions of diaryl sulfones with diarylmethanes

Treatment of dibenzothiophene dioxides with cyclic diarylmethanes in the presence of KN(SiMe3)2 results in the formation of fluorene-based spirocyclic tetraarylmethanes in a single operation. The transformation would proceed via an intermolecular SNAr reaction of the dioxides with cyclic diarylmethylpotassium followed by intramolecular SNAr cyclization. This straightforward strategy provides a wide range of spirocyclic diarylfluorenes including unusual ones that are otherwise difficult to synthesize.

Palladium-catalyzed arylation of methylene-bridged polyarenes: Synthesis and structures of 9-arylfluorene derivatives

In the presence of a catalytic system comprised of palladium(II) acetate and tricyclohexylphosphine, the reaction of fluorene with haloarenes generated 9-arylfluorenes in good to excellent yields. The scope and limitations of the coupling reaction were investigated. This synthetic protocol is more efficient than conventional methods. A wide range of functional groups, including alkyl, alkoxy, ester, and nitrile, can tolerate the reaction conditions herein. Sterically congested haloarenes also gave satisfactory results. Furthermore, this synthetic method is utilized to prepare 9,9-diarylfluorenes and tetraarylindenofluorene. Depending on the reaction conditions, the arylation of bowl-shaped sumanene gave monoarylated sumanene either as the sole product or with another diaryl-substituted product. Copyright

Non-catalytic conversion of C-F bonds of benzotrifluorides to C-C bonds using organoaluminium reagents

A facile method for the conversion of C-F bonds of benzotrifluorides to C-C bonds has been developed using aluminium reagents in the absence of catalysts.

A general and efficient synthesis of substituted fluorenes and heterocycle-fused indenes containing thiophene or indole rings utilizing a Suzuki-Miyaura coupling and acid-catalyzed Friedel-Crafts reactions as key steps

A general and efficient synthesis of fluorenes or heterocycle-fused indenes including 3-thia-cyclopenta[a]indenes, 9-thia-indeno[1,2-a]indenes, 5,6-dihydroindeno[2,1-b]indoles has been developed. This methodology is realized by a multistep protocol involv

Syntheses and Reactions of 9-Substituted 10-Phenylthioxanthenium Salts: Negative Evidence for Thia-anthracene Oligomerisation

Various 9-aryl-10-phenylthioxanthenium salts have been prepared and their stereochemistry determined by (1)H n.m.r. spectroscopy.Reactions of the 10-phenylthioxanthenium salts or 10-phenyl-10-thia-anthracenes with aryl-lithiums have been studied in order to investigate whether or not 10-thia-antracenes cause oligomerisation.The 10-phenylthioxanthenium salts reacted with aryl-lithiums to give 9-phenylthioxanthenes in good yields.However, 10-phenylthioxanthenium salt (19) when treated with phenyl-lithium at -15 to -20 deg C gave 9-phenylthioxanthenol (38) (17percent) together with 9-phenylthioxanthene (13) because of the lability of 10-phenyl-10-thia-anthracene to air. 10-Phenyl-9-(p-tolyl)-10-thia-anthracene (50) generated in situ from the sulphonium salt (22) and lithium diisopropylamide failed to react with p-tolyl-lithium.An isolable ylide, 9-benzoyl-10-phenyl-10-thia-anthracene (52) was treated with p-tolyl-lithium at 0 deg C to give 9-benzoylthioxanthene (4) (82percent).In contrast, 9,9,10-triphenylthioxanthenium salt (24) on treatment with phenyl-lithium gave a ring-opened product (40), a ring-contracted product (41), diphenylsulphide (42), and 9,9-diphenylthioxanthene (12).These results indicate that the 10-phenyl-thia-anthracenes or the ?-sulphuranes of thioxanthenes do not cause oligomerisation.

REACTION OF TRIPHENYLMETHYLCATION IN TRIFLUOROMETHANESULFONIC ACID. REACTION OF CARBODICATIONS

Triphenylmethyl cation reacts in the presence of trifluoromethanesulfonic acid in benzene.Products are 9-phenylfluorene, 9,9-diphenylfluorene, and triphenylmethane.A protonated triphenylmethyl cation and a protonated 9-phenylfluorenyl cation are postulated as intermediates.

REGIOSELECTIVE DIMETALLIERUNG VON AROMATEN. BEQUEMER ZUGANG ZU 2,2'-DISUBSTITUIERTEN BIPHENYLDERIVATEN

Lithiation of biphenyl with 2.4 mol of n-butyllithium in the presence of TMEDA led directly to the 2,2'-dilithio derivative (I) in modest, but preparatively useful yields.I, in turn, was converted to a variety of products.The activation of the 2'-position of 2-lithiobiphenyl was shown directly by a separate experiment.MNDO calculations indicate stabilization in I by double bridging and in 2-lithiobiphenyl by intramolecular ? interaction of Li with the o-phenyl group.Similar interactions in substitution transition states rationalize the specificity of the reactions observed.