474918-32-6

Basic information

• Product Name: 2-Bromo-9,9-diphenylfluorene
• Synonyms: 9H-Fluorene, 2-bromo-9,9-diphenyl-;2-bromo-9,9-diphenylfluorene;2-bromo-9,9-diphenyl-fluororene;2-Bromo-9,5-diphenylfluorene;2--9,9--;2-Dibromo-9,9-diphenylfluorene;2-Bromo-9,9-diphenyl;2-BroMo-9,9-diphenyl-9H-fluorene
• CAS NO: 474918-32-6
• Molecular Formula: C₂₅H₁₇Br
• Molecular Weight: 397.31
• EINECS: 1312995-182-4
• Product Categories: Fluorene Derivatives;OLED materials,pharm chemical,electronic
• Mol File: 474918-32-6.mol

Chemical Properties

• Melting Point: 217.0 to 221.0 °C
• Boiling Point: 480.5 °C at 760 mmHg
• Flash Point: 235.7 °C
• Appearance: /
• Density: 1.363 g/cm³
• Refractive Index: 1.681
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Toluene
• CAS DataBase Reference: 2-Bromo-9,9-diphenylfluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-9,9-diphenylfluorene(474918-32-6)
• EPA Substance Registry System: 2-Bromo-9,9-diphenylfluorene(474918-32-6)

Safety Data

• Hazardous Substances Data: 474918-32-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics Industry:
2-Bromo-9,9-diphenylfluorene is used as a key intermediate for the synthesis of 9,9-diphenylfluorene-capped oligothiophenes, which serve as active materials in field-effect transistors and light-emitting diodes. Its high fluorescent properties and electron delocalization make it a valuable component in the development of efficient and high-performance organic electronic devices.
Used as a Non-Linear Optical (NLO) Material:
Due to its π-electron conjugation and high electron delocalization, 2-bromo-9,9-diphenylfluorene can be utilized as a non-linear optical material. This application is particularly relevant in the field of photonics, where materials with non-linear optical properties are essential for the development of advanced optical devices and systems.

Synthesis

10 g (30 mmol) of 2-bromo-9-phenyl-9H-fluoren-9-ol was dissolved in 60 ml of benzene, and 2.4 ml (45 mmol) of concentrated sulfuric acid diluted with a small amount of benzene was added to the solution. The mixture was stirred for 5 hours at 80° C, and after evaporating the benzene, 1 N sodium hydroxide solution was added to the remaining solution to a pH of around 7. The mixture was extracted 3 times with ethyl acetate (40 ml). The collected organic layer was dried with magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography. 6 g of Intermediate N (yield: 50%).

References

(2015). Synthesis method of 2-bromo-9, 9-diphenylfluorene, Google Patents. Wong, Ken-Tsung, et al. "Synthesis and properties of novel thiophene-based conjugated homologues: 9, 9-diphenylfluorene-capped oligothiophenes."Organic letters 4.25 (2002): 4439-4442.

InChI:InChI=1/C25H17Br/c26-20-15-16-22-21-13-7-8-14-23(21)25(24(22)17-20,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H

Upstream product

• 108-86-1 bromobenzene 
• 486-25-9 9-fluorenone 
• 3096-56-8 2-bromofluoren-9-one 
• 100-58-3 phenylmagnesium bromide 
• 17103-26-3 methyl 4'-bromo-[1,1'-biphenyl]-2-carboxylate 
• 71-43-2 benzene 
• 736928-22-6 2-bromo-9-phenyl-9-hydroxyfluorene 

Downstream Products

• 462128-39-8 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-diphenyl-9H-fluorene 
• 1008530-48-0 C₆₂H₄₄Si 
• 1008530-49-1 C₅₄H₄₆OSi₂ 
• 1158844-76-8 C₃₁H₂₂ 
• 1158844-77-9 C₃₁H₂₀Br₂ 
• 1158844-78-0 C₄₃H₄₄B₂O₄ 
• 1221237-90-6 C₃₁H₂₁Cl 
• 1221237-91-7 C₃₇H₂₇N 
• 1221237-18-8 C₆₂H₄₄N₂ 
• 1334287-59-0 4-(9,9-diphenyl-9H-fluoren-2-yl)benzaldehyde 
• 400607-31-0 (9,9-diphenyl-9H-fluoren-2-yl)boronic acid 
• 1601479-57-5 1,2-bis(4-(9,9-diphenyl-9H-fluoren-2-yl)phenyl)-1,2-diphenylethene 
• 1610059-33-0 C₇₇H₇₁N₃ 

Relevant articles and documents

Preparation method 2 -amino -9-9 - diphenyl fluorene

The invention discloses a preparation method of 2 - amino -9 and 9 - diphenyl fluorene, which comprises the following steps: taking 9 - fluorenone as a raw material, and carrying out bromination reaction to obtain 2 - bromo -9 - fluorenone. 2 - Bromo -9 - fluorenone and bromobenzene formative reagent are reacted to obtain 2 - bromo -9 - phenyl -9 - hydroxyl - fluorene. 2 - Bromo -9 - phenyl -9 - hydroxy - fluorene was subjected to an alkylation reaction with benzene to give 2 - bromo -9, 9 - diphenylfluorene. 2 - Bromo -9, 9 - diphenylfluorene and cuprous oxide, palladium acetate (II) and N - methylpyrrolidinone were reacted in liquid ammonia to give 2 - amino -9, 9 - diphenylfluorene. The preparation method is used for preparing 2 - amino -9 and 9 - diphenylfluorene, the used preparation is easy to obtain, the technological process is simple, the product yield is high, the production cost is reduced, 2 - amino -9 and 9 - diphenyl fluorene are produced.

A 2 - bromo - 9, 9 - diphenyl wu synthetic method

The invention discloses a synthetic method of 2-bromo-9,9-diphenyl fluorene. The synthetic method comprises the following steps: (1) mixing trifluoroacetic acid, aluminium chloride anhydrous and benzene in a molar ratio to obtain A liquid; (2) mixing 2-bromo-9-phenyl-fluoren-9-ol and benzene in a molar ratio to obtain B liquid; (3) under gas shield, mixing the A liquid and the B liquid in proportion while stirring, and controlling the system temperature to be not over 50 DEG C at the same time; (4) raising the temperature to be 65-75 DEG C, reacting for 1-1.5 h, supplementing trifluoroacetic acid, and continuously reacting for 2-4 h; and (5) separating and purifying to obtain the 2-bromo-9,9-diphenyl fluorene. The synthetic method is simple in operation and mild in reaction condition, has higher yield and lower cost, and has wide industrial popularization prospect.

2 - bromo - 9, 9 - diphenyl wu synthetic method

The invention provides a synthesis method of 2-bromo-9,9-diphenylfluorene and belongs to the technical field of organic synthesis. The synthesis method comprises steps as follows: (1), after 2-bromo-9-phenyl-fluorene-9-ol and benzene are mixed, reaction gas is introduced for a reaction at the temperature of 61-66 DEG C while the components are stirred, the temperature is increased and backflow is performed after gas introduction is finished, and water is separated while backflow is performed; (2), a catalyst is added in 0.5-1 h after a system obtained from the step (1) is cooled, the temperature is increased to 35-50 DEG C, and the mixture reacts for 3.5-5 h; (3), 2-bromo-9,9-diphenylfluorene is obtained through separation and purification. The synthesis method of 2-bromo-9,9-diphenylfluorene is low in cost, especially when hydrogen chloride and hydrogen bromide are utilized; with the adoption of an aluminum trichloride anhydrous and ferric chloride anhydrous mixed catalysis mode, the catalysis effect is good, the reaction time is short, and the yield is high; the operation is simple, the process is reliable, and scale-up is facilitated.

Process for preparing 2 - bromo - 9, 9 - diphenyl wu

The invention relates to a one-pot method for preparing 2-bromo-9,9-diphenylfluorene and belongs to the technical field of organic synthesis. The method comprises steps shown in the specification. The reaction can be finished in one reactor, particularly for a chlorination reaction, intermediate products are not required to be separated out, a subsequent reaction of replacement of chlorine atoms with benzene rings is performed after a system reactant and a catalyst are directly added, the whole operation is simple, and the technology is reliable and suitable for enlargement; besides, by means of the used catalyst, side reactions can be effectively reduced, the product yield is increased to be higher than 90%, meanwhile, separation can be realized through filtration after the reaction due to the fact that the catalyst is a solid catalyst, and the after-treatment process is simplified.

DERIVATIVES OF 2-DIARYLAMINOFLUORENE AND ORGANIC ELECTRONIC COMPOUNDS CONTAINING THEM

The present invention relates to certain fluorenes, to the use of the compounds in an electronic device, and to an electronic device comprising at least one of these compounds. The present invention furthermore relates to a process for the preparation of the compounds and to a formulation and composition comprising one or more of the compounds.

Novel tri-carbazole modified fluorene host material for highly efficient solution-processed blue and green electrophosphorescent devices

A series of novel solution-processable small-molecule host materials: 2DPF-TCz, 2SBF-TCz, 27DPF-TCz, and 27SBF-TCz comprising a fluorene monomer as the rigid core and tri-carbazole as the periphery have been designed and synthesized, and their optical, electrochemical, and thermal properties have been fully characterized. The host materials exhibit high glass-transition temperatures (231-310 °C) and high triplet energy levels (2.61-2.73 eV). High-quality amorphous thin films can be obtained by spin-coating the host materials from solutions. It is found that the HOMO level of the host materials can be tuned by linking the tri-carbazole unit to the 2,7 positions of the fluorine core, resulting in appropriate HOMO energy levels (-5.36 to -5.23 eV) for improved hole-injection in the device. Solution-processed blue and green electrophosphorescent devices bases on the developed host materials exhibit high efficiencies of 21.2 and 34.8 cd A-1, respectively.

LUMINESCENT COMPOUNDS AND ELECTROLUMINESCENT DEVICE USING THE SAME

The present invention relates to organic electroluminescent compounds and organic electroluminescent devices employing the same. More specifically, the invention relates to organic electroluminescent compounds containing an anthracenyl group or an aryl group having an anthracenyl substituent m the aryl ring of fluorene or indenofluorene, as a blue electroluminescent material in an organic electroluminescent layer. The electroluminescent compounds according to the invention exhibit high luminous efficiency and excellent life property, so that an OLED device having very good operation lifetime can be prepared therefrom.

Synthesis and photophysical properties of pyrrole/polycyclic aromatic units hybrid fluorophores

A series of pyrrole/polycyclic aromatic unit hybrid fluorophores was developed by a two-stage synthetic strategy. Their central aryl-substituted pyrrole cores were constructed by a Paal-Knorr pyrrole synthesis reaction. The reaction conditions and mechanism are also discussed in detail. End-capping triflate onto the central pyrrole core enables the core to incorporate various polycyclic aromatic units. The Buchwald-Hartwig amination reaction and the Suzuki-Miyaura cross-coupling reaction were adopted to incorporate the triflate end-capping pyrrole with N-phenylnaphthalen-1-amine and various polycyclic aromatic units to form the hybrid fluorophores. The photophysical properties and thermal properties of the fluorophores were characterized. Most of the pyrrole fluorophores emitted blue light and exhibited high quantum efficiency. The fluorescence properties of these pyrrole fluorophores were induced by manipulating the surrounding polycyclic aromatic units. When the central pyrrole core was incorporated with amino or naphthalene moieties, the fluorescence efficiency and thermal stability of fluorophores 1 and 2 were low (φf g f > 0.99) and stable glassy morphology (the Tg value of the fluorophore 6 was as high as 220 °C). Results of this study demonstrate that the sterically induced fluorescence of crowded pyrrole and the fluorescent polycyclic aromatic units significantly affect the emission properties of the hybrid fluorophores.

Ter(9,9-diarylfluorene)s: Highly efficient blue emitter with promising electrochemical and thermal stability

Novel ter(9,9-diarylfluorene)s were synthesized by a Suzuki-coupling reaction of 2-bromofluorene (1) and 2,7-fluorenediboronic ester derivatives (3) with high isolated yields (63-86%). The X-ray structure analysis of ter(9,9′-spirobifluorene) (4aa) revealed that the conjugated chromophore adopts a helical conformation. This conformation effectively releases the steric interaction between the fluorene moieties and prevents inter-chromophore interactions. The introduction of aryl groups at the C9 position of fluorene was highly beneficial to the thermal and morphological stability of these oligomers. These terfluorenes exhibit intense blue fluorescence with excellent quantum yields both in solution (～100%) and in solid state (66-90%), and possess interesting reversible redox properties. Highly efficient blue light-emitting OLED devices were fabricated using 4aa and 4cc as emitters as well as hole transporters. The devices exhibit low turn-on voltage (～3 V) and high EL external quantum efficiency (2.5-3%). Copyright