198964-46-4

Basic information

• Product Name: 9,9-Dioctyl-2,7-dibromofluorene
• Synonyms: 9,9-DioCLyl-2,7-DibroMofluorene;9H-Fluorene, 2,7-dibroMo-9,9-dioctyl-;9,9-Dioctyl-2,7-dibroMoflurene;9H-Fluorene, 2,7-dibroMo-9,9-dioctyl- 2,7-DibroMo-9,9-bis(n-octyl)fluorene;9,9-Dioctyl-2,7-dibroMofluorene 96%;9 9-DIOCTYL-2 7-DIBROMOFLUORENE 96;9,9-Dioctyl-2,7-diformylfluorne;9,9-Dioctyl-2,7-dibromofluorene
• CAS NO: 198964-46-4
• Molecular Formula: C₂₉H₄₀Br₂
• Molecular Weight: 548.44
• EINECS: 1312995-182-4
• Product Categories: OLED materials,pharm chemical,electronic;Fluorene Derivatives;Organic Electronics and Photonics;Polyfluorene (PFO, PFE) Monomers;Synthetic Tools and Reagents;Fluorene Series
• Mol File: 198964-46-4.mol
• Article Data: 94

Chemical Properties

• Melting Point: 59-63 °C(lit.)
• Boiling Point: 567.211 °C at 760 mmHg
• Flash Point: 341.372 °C
• Appearance: /solid
• Density: 1.212 g/cm³
• Vapor Pressure: 2.69E-12mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 9,9-Dioctyl-2,7-dibromofluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,9-Dioctyl-2,7-dibromofluorene(198964-46-4)
• EPA Substance Registry System: 9,9-Dioctyl-2,7-dibromofluorene(198964-46-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37/39-26
• WGK Germany: 2
• Hazardous Substances Data: 198964-46-4(Hazardous Substances Data)

Usage

Description

9,9-Dioctyl-2,7-dibromofluorene is a white solid that serves as a crucial reactant in the synthesis of various polymer semiconductors. It is particularly utilized in the creation of donor-acceptor type photoelectrical materials, which are essential components in advanced electronic devices.

Uses

Used in Organic Light-Emitting Diodes (OLEDs):
9,9-Dioctyl-2,7-dibromofluorene is used as a reactant for synthesizing 5,5''-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(thiophene-2-carbaldehyde), a key component in the development of OLEDs. This photoelectrical material contributes to the efficient light emission and energy transfer properties of OLEDs, making them suitable for use in display and lighting applications.
Used in Organic Photovoltaic (OPVs):
In the field of organic photovoltaics, 9,9-Dioctyl-2,7-dibromofluorene is employed as a reactant to produce polymer semiconductors that enhance the light absorption and charge transport capabilities of OPVs. This improves the overall efficiency and performance of solar cells, making them more viable for renewable energy applications.
Used in Organic Field-Effect Transistors (OFETs):
9,9-Dioctyl-2,7-dibromofluorene is also used as a reactant in the synthesis of polymer semiconductors for OFETs. These materials are crucial for the development of flexible and lightweight electronic devices, such as sensors, displays, and wearable electronics, due to their high charge carrier mobility and compatibility with solution-based processing techniques.
Used in Polymer Synthesis:
9,9-Dioctyl-2,7-dibromofluorene is used as a building block in the synthesis of various polymer semiconductors through Suzuki coupling or Stille coupling reactions. These polymers find applications in a wide range of electronic and optoelectronic devices, showcasing the versatility and importance of 9,9-Dioctyl-2,7-dibromofluorene in the field of materials science.

InChI:InChI=1/C29H40Br2/c1-3-5-7-9-11-13-19-29(20-14-12-10-8-6-4-2)27-21-23(30)15-17-25(27)26-18-16-24(31)22-28(26)29/h15-18,21-22H,3-14,19-20H2,1-2H3

Upstream product

• 123863-99-0 9,9-dioctyl-9H-fluorene 
• 111-83-1 1-bromo-octane 
• 16433-88-8 2,7-dibromo-9H-fluorene 
• 1310-73-2 sodium hydroxide 
• 86-73-7 9H-fluorene 
• 14348-75-5 2,7-dibromofluorene-9-one 
• 629-27-6 1-Iodooctane 

Downstream Products

• 196207-58-6 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene 
• 258865-48-4 9,9-dioctyl-9H-fluorene-2,7-diyldiboronic acid 
• 620624-96-6 2-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolane-2'-yl)-7-bromo-9,9-bisoctylfluorene 
• 778641-67-1 2,7-bis-(4-methoxy-phenyl)-9,9-dioctyl-9H-fluorene 
• 850153-27-4 4-(7-bromo-9,9-dioctyl-9H-fluoren-2-yl)-N,N-diphenylaniline 
• 86-73-7 9H-fluorene 
• 123863-99-0 9,9-dioctyl-9H-fluorene 
• 915031-04-8 N,N'-bisphenyl-9,9-dioctyl-9H-fluorene-2,7-diamine 
• 415707-95-8 2,7-bis(4-phenylcarboxylic acid methyl ester)-9,9-di-n-octylfluorene 
• 415708-05-3 2,7-bis(4-phenylcarboxylic acid)-9,9-di-n-octylfluorene 
• 893402-97-6 2,7-bis(4-phenylcarboxylic acid)-9,9-di-n-octylfluorene disuccimidyl ester 
• 317802-08-7 2,7-bis(1,3,2-dioxaborinan-2-yl)-9,9-dioctylfluorene 
• 778641-69-3 C₄₁H₅₀O₂ 

Relevant articles and documents

Synthesis and ring opening reaction of octaoctyl substituted [2.2.2.2](2,7)-fluorenophanetetraene by photooxidation

Octaoctyl substituted fluorenophanetetraene has been synthesized from its corresponding octaoctyl substituted tetrathia[3.3.3.3]fluorenophane followed by benzyne Stevens rearrangement, oxidation and thermal elimination. The solid-state structure of octaoctyl substituted [2.2.2.2](2,7)-fluorenophanetetraene reveals that fluorene units are connected by cis vinylenes and alkyl chains are located inside and outside the rings. The photooxidation reaction of the fluorenophanetetraene was carried out in a dilute solution under UV light irradiation to give all trans linear fluorenevinylene with aldehyde end groups. The optical properties of the fluorenophanetetraene and its linear compound generated by photooxidation have been investigated and compared. The fluorescence quantum yield of the fluorenophanetetraene in solution is much lower than that of its linear compound generated by photooxidation due to shorter effective conjugation lengths; however, the fluorescence intensity of the fluorenophanetetraene in the solid state is much higher than that of its linear compound generated by photooxidation possibly due to weak intermolecular interaction.

Facile synthesis of fluorene-based π-conjugated polymers via sequential bromination/direct arylation polycondensation

The synthesis of fluorene-based π-conjugated polymers via sequential bromination and Pd-catalyzed direct arylation polycondensation was demonstrated; the protocol allows dual functionalization of each aromatic monomer in one-pot fashion. This synthetic protocol afforded the corresponding polymers with high molecular weights in good yields (up to yield 80%, Mn 34,500).

A supramolecular approach to lithium ion solvation at nanostructured dye sensitised inorganic/organic heterojunctions

A novel arylamine based hole transporting material (HTM) with tetraethylene glycol (TEG) side groups is reported. Lithium ions solubilised by the TEG groups are employed to modulate interfacial electron transfer reactions at a dye sensitised TiO2/su

High-efficiency red-light emission from polyfluorenes grafted with cyclometalated iridium complexes and charge transport moiety

We report a new route for the design of electroluminescent polymers by grafting high-efficiency phosphorescent organometallic complexes as dopants and charge transport moieties onto alky side chains of fully conjugated polymers for polymer light-emitting diodes (PLED) with single layer/single polymers. The polymer system studied involves polyfluorene (PF) as the base conjugated polymer, carbazole (Cz) as the charge transport moiety and a source for green emission by forming an electroplex with the PF main chain, and cyclometalated iridium (Ir) complexes as the phosphorescent dopant. Energy transfer from the green Ir complex or an electroplex formed between the fluorene main chain and side-chain carbazole moieties, in addition to that from the PF main chain, to the red Ir complex can significantly enhance the device performance, and a red light-emitting device with the high efficiency 2.8 cd/A at 7 V and 65 cd/m2, comparable to that of the same Ir complex-based OLED, and a broad-band light-emitting device containing blue, green, and red peaks (2.16 cd/A at 9 V) are obtained. Copyright

Efficient design and structural modifications for tuning the photoelectric properties of small-molecule acceptors in organic solar cells

Five novel small molecules were designed and synthesized to investigate the relationships between molecular structures and photoelectric properties. Firstly, three A1-A-A1 type molecules, incorporating a 2,1,3-benzothiadiazole (BT) unit with no, one or two fluorine atoms as the core, 2-ethylhexyl-substituted phthalimide (PI) as the terminal moiety and ethynyl functionalized thiophene as the π-linker, were synthesized to explore the effect of fluorination on photoelectric properties, namely (PIAT)2BT, (PIAT)2fBT and (PIAT)2dfBT. By introducing fluorine atoms on the molecular backbone, both the HOMO and LUMO energy levels can be tuned efficiently, with minimal influence on optical absorption. Next, on the basis of the BT-based molecules, two extended molecules containing diketopyrrolopyrrole (DPP) were constructed, namely (PIAT)2DPP and FADPPPI, improving optical absorption successfully, especially for FADPPPI with an absorption edge of 850 nm in the film. Considering the photoelectric properties of the above five molecules, poly(3-hexylthiophene) (P3HT) was chosen as the electron donor material to pair with these molecules, and preliminary device fabrication and investigation of photovoltaic performances were performed. These results demonstrate that our materials show great potential in being small-molecule acceptors for organic solar cells (OSCs), and further research on device fabrication and optimization is in progress in our laboratory.

High-efficiency polymer solar cells via the incorporation of an amino-functionalized conjugated metallopolymer as a cathode interlayer

An amino-functionalized conjugated metallopolymer PFEN-Hg was developed as a cathode interlayer for inverted polymer solar cells. The resulting devices exhibited significantly improved performance with power conversion efficiencies exceeding 9%. Moreover, good device performance was achievable with the PFEN-Hg over a wider range of film thickness, likely due to the Hg-Hg interactions and improved π-π stacking.

Novel water-soluble light-emitting materials prepared by noncovalently bonded self-assembly

Novel noncovalently connected water-soluble nanoparticles containing hydroxyl-capped polyfluorene (PFOH) and poly-(acrylic acid) (PAA) were obtained and characterized. These nanoparticles were quite stable in water and no precipitate was observed after weeks. Transmission electron microscopy (TEM), scanning electron microscopy (SEM), and laser light scattering (DLS) were used to confirm the morphology of the PFOH/PAA nanoparticles. Their optical properties were investigated and showed the similar optoelectronic properties with PFOH solid film. Copyright

SOLAR CELL DYES FOR COPPER REDOX BASED DYE SENSITIZED SOLAR CELLS AND COMBINATIONS THEREOF

The present application discloses compounds and compositions, useful in the manufacture of dye-sensitized solar cells and other similar technology.

Star-shaped oligofluorene truxene macromolecules - Synthesis and properties as a function of alkyl chain length

Star-shaped oligofluorene truxenes are very promising materials and have demonstrated excellent properties as the gain medium in organic semiconductor lasers (OSLs).1-10 Alkyl chains in oligofluorene truxenes act as solubilizing groups as well as spacers to prevent intermolecular π-π stacking that leads to quenching of the light emission. A new series of star-shaped systems analogous to hexyl oligofluorene truxenes11 with alkyl chains of different lengths (butyl chains and octyl chains) was synthesized. The objective of this study was to investigate the effect of alkyl chain length on the film-forming properties of oligofluorene-truxene materials and, as a result, on their optoelectronic properties for applications as the gain medium in OSLs.