128055-74-3

Basic information

• Product Name: 2,2',7,7'-Tetrabromo-9,9'-spirobifluorene
• Synonyms: 2,2',7,7'-TETRABROMO-9,9'-SPIROBIFLUORENE;2,2'',7,7''-TETRABROMO-9,9''-SPIRO-BIFLUOROENE;2,2'',7,7''-TETRABROMO-9,9''-SPIROBI[9H-FLUORENE];2,2',7,7'-Tetrabromo-9,9'-spirobiflurene;2,2',7,7'-Tetrabromo;2,2',7,7'-TetrabroMo-9,9'-Spirobifluorene,TetrabroMo-9,9'-Spirobifluorene;9,9'-Spirobi[9H-fluorene], 2,2',7,7'-tetrabroMo- 2,2',7,7'-TetrabroMo-9,9'-spirobi[9H-fluorene];TetrabroMo-9,9'-spirobifl
• CAS NO: 128055-74-3
• Molecular Formula: C₂₅H₁₂Br₄
• Molecular Weight: 631.98
• EINECS: 1312995-182-4
• Product Categories: Fluorene Derivatives;Fluorene Series
• Mol File: 128055-74-3.mol

Chemical Properties

• Melting Point: 395-400°C
• Boiling Point: 633.7 °C at 760 mmHg
• Flash Point: 322.5 °C
• Appearance: off-white crystal
• Density: 2.12 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform
• CAS DataBase Reference: 2,2',7,7'-Tetrabromo-9,9'-spirobifluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2',7,7'-Tetrabromo-9,9'-spirobifluorene(128055-74-3)
• EPA Substance Registry System: 2,2',7,7'-Tetrabromo-9,9'-spirobifluorene(128055-74-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 128055-74-3(Hazardous Substances Data)

Usage

Uses

Used in OLED Industry:
2,2',7,7'-Tetrabromo-9,9'-spirobifluorene is used as a blue light emitting material for the preparation of OLEDs. Its application is particularly focused on utilizing amorphous compounds with a spiro-bifluorene core, which contributes to the device's efficiency and performance. The compound's ability to decrease crystallization and prevent aggregate or excimer formation results in improved color stability and overall device quality.

Upstream product

• 159-66-0 9,9'-spirobifluorene 
• 2052-07-5 2-Bromobiphenyl 
• 67665-44-5 9-((1,1'-biphenyl)-2-yl)-9H-fluoren-9-ol 
• 90-41-5 2-phenylaniline 
• 171408-84-7 2,7-dibromo-9,9'-spirobi[fluorene] 
• 486-25-9 9-fluorenone 
• 2113-51-1 2-iodobiphenyl 

Downstream Products

• 128055-75-4 2,2',7,7'-tetrakis(4''-(trimethylsilyl)phenyl)-9,9'-spirobifluorene 
• 171408-92-7 2,2',7,7'-Tetraphenyl-9,9'-spirobifluorene 
• 1267662-20-3 C₆₅H₇₂Si₄ 
• 1357929-84-0 C₈₁H₆₈N₄O₄ 
• 1425942-31-9 2,2',7,7'-tetrakis(3,4,5-trifluorophenyl)spiro-9,9'-bifuorene 
• 1425942-32-0 2,2',7,7'-tetrakis(3,5-bis(trifluoromethyl)phenyl)spiro-9,9'-bifuorene 
• 1425942-33-1 2,2',7,7'-tetrakis(2-(trifluoromethyl)phenyl)spiro-9,9'-bifuorene 
• 1425942-28-4 2,2',7,7'-tetrakis(2-fluorophenyl)spiro-9,9'-bifuorene 
• 1425942-29-5 2,2',7,7'-tetrakis(3-fluorophenyl)spiro-9,9'-bifuorene 
• 723285-23-2 2,2',7,7'-tetrakis(3-fluorophenyl)spiro-9,9'-bifuorene 
• 1425942-30-8 2,2',7,7'-tetrakis(2,4-bifluorophenyl)spiro-9,9'-bifuorene 
• 1573202-44-4 N²,N²,N^2',N^2',N⁷,N⁷,N^7',N^7'-octakis(3-methoxypheny)-9,9'-spirobi[fluorene]-2,2',7,7'-tetraamine 
• 1628961-22-7 N²,N²,N^2',N^2',N⁷,N⁷,N^7',N^7'-octakis(2-methoxypheny)-9,9'-spirobi[fluorene]-2,2',7,7'-tetraamine 
• 207739-72-8 N²,N²,N^2',N^2',N⁷,N⁷,N^7',N^7'-octakis(4-methoxypheny)-9,9'-spirobi[fluorene]-2,2',7,7'-tetraamine 

Relevant articles and documents

Toward stable interfaces in conjugated polymers: Microporous poly(p-phenylene) and poly(phenyleneethynylene) based on a spirobifluorene building block

Conjugated polymer networks based on spirobifluorene building units exhibit defined photoluminescence as well as pronounced microporosity, that is, large, stable interfaces. Copyright

Bigger and Brighter Fluorenes: Facile π-Expansion, Brilliant Emission and Sensing of Nitroaromatics

π-Expanded butterfly-like 2D fluorenes and 3D spirobifluorenes 1–5 were synthesized via a DDQ-mediated oxidative cyclization strategy with a high regioselectivity. Through structural modification via π-expansion, it was possible to achieve near-ultraviolet absorption, bright-blue emission, very high near-unity fluorescence quantum yields in solution as well as in film states, and deep-lying HOMO energy levels with excellent thermal stabilities. Furthermore, these electron-rich compounds displayed a notable behavior towards sensing of nitroaromatic explosives, such as picric acid, up to a detection limit of 0.2 ppb.

Synthesis of Conjugated Copolymer Containing Spirobifluorene Skeleton by Acyclic Diene Metathesis Polymerization for Polymer Light-Emitting Diode Applications

Grubbs-type, Hoveyda-type, cyclic alkyl amino carbene (CAAC)-based ruthenium olefin metathesis catalysts were used for the acyclic diene metathesis (ADMET) polymerization of 2,7-divinyl-9,9-di-n-octylfluorene (DVF). Additionally, various ratios of DVF and 2,2′,7,7′-tetravinyl-9,9′-spirobifluorene (TVSF) were subjected to ADMET polymerization to obtain polymers P1–P7. Polymers P1–P4 were analyzed with gel permeation chromatography, UV–vis spectroscopy, and photoluminescence spectroscopy. As the TVSF ratio increases, polymers exhibit lower solubility but a narrower band in the photoluminescence spectrum. Polymer light-emitting diode (PLED) devices were fabricated with polymers P1, P2, and P3. The performances of the PLED devices indicated that polymers including more spirobifluorene blocks showed better turn-on voltage, brightness, current efficiency, and power efficiency.

Nonlinear-Optical Behaviors of a Chiral Metal-Organic Framework Comprised of an Unusual Multioriented Double-Helix Structure

We present here the synthesis of one enantiomeric pair of metal-organic framework materials comprised of a unique multioriented double-helix structure from an achiral spirocenter ligand. Our study clearly shows that the chiral MOF material encompasses concurrently multiple nonlinear-optical functions in the solid state: the noncentrosymmetric structural feature brings the chiral MOF high second-harmonic-generation efficiency; the incorporation of the spirocenter ligand can efficiently produce two-photon-excited photoluminescence with a larger-action cross-sectional value.

Facile synthesis of a hole transporting material with a silafluorene core for efficient mesoscopic CH3NH3PbI3 perovskite solar cells

A novel electron-rich small-molecule, 4,4′-(5,5-dihexyl-5H-dibenzo[b,d]silole-3,7-diyl)bis(N,N-bis(4-methoxyphenyl)aniline) (S101), containing silafluorene as the core with arylamine side groups, has been synthesized via a short efficient route. When S101 was incorporated into a CH3NH3PbI3 perovskite solar cell as a hole transporting material (HTM), a short circuit photocurrent density (Jsc) of 18.9 mA cm-2, an open circuit voltage (Voc) of 0.92 V, and a fill factor (FF) of 0.65 contributing to an overall power conversion efficiency (PCE) of ～11% which is comparable to the PCE obtained using the current state-of-the-art HTM 2,2′,7,7′-tetrakis(N,N′-di-p-methoxyphenylamine)-9,9′-spirobifluorene (spiro-OMeTAD) (η = 12.3%) were obtained. S101 is thus a promising HTM with the potential to replace the expensive spiro-OMeTAD due to its comparable performance and much simpler and less expensive synthesis route.

HETEROATOMIC-BASED HOLE-TRANSPORT MATERIALS

Heteroatomic hole transport materials are provided. The hole transport materials include a non-carbon core: two, four, or eight aromatic groups covalently bound to the non-carbon core; a. terminal substituted diphenylamine end unit on each aromatic group: and optionally aromatic linker groups linking the aromatic groups and the substituted diphenylamine end units. In some embodiments the non-carbon core is non-carbon central atom such as Si, Ge, B?, P+Sn or Pb. In other embodiments, the non-carbon core is a cubic silsesquioxane. Also provided are methods for making these materials. The materials are particularly useful as hole transport materials in perovskite solar cells.

Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides

A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.

{[Ru(bda)]:XLy}n cross-linked coordination polymers: Toward efficient heterogeneous catalysis for water oxidation in an organic solvent-free system

Recently, the development of polymeric catalysts for water splitting has received an increasing amount of attention. In this study, we successfully developed a few novel cross-linked coordination polymers (CCPs) with the formula {[Ru(bda)]xLy}n as efficient heterogeneous catalysts for water oxidation in an organic solvent-free system, where Ru(bda) represents the catalytic center. Detailed water oxidation catalytic kinetics studies suggested that single-site water nucleophilic attack (WNA) is the general mechanism applied to these polymeric catalysts, which is different to the small-molecular reference, [Ru(bda)(pic)2] (pic = 4-picoline). The experimental evidence also indicated the importance of interfacial wettability and the existence of the Ru(bda)-macrocyclic fragments in the polymer network in determining the overall catalytic activity. More interestingly, end-capping modification via the pyridine/DMSO exchange reaction further removed the residual Ru(DMSO)x moieties on the surfaces of the polymer network, which leads to the improved performance with an impressive TOF of ～4.6 s-1 and TON of ～750 in an organic solvent-free system, which are superior to [Ru(bda)(pic)2]. The rate of catalysis is among the highest for a heterogeneous system reported to date. An electrochemical study showed the polymeric catalysts were also promising electrode materials for electrocatalytic water oxidation and an electrode based on CCP/Nafion/ITO maintained ～73% of its initial activity after 27 cycles under the optimal conditions.

Spirofluorene compound and light-emitting device thereof

The invention relates to the technical field of organic light-emitting materials and particularly relates to a spirofluorene compound and a light-emitting device thereof. A spirobifluorene compound is selected from a compound represented by formula I (shown in the description), wherein Y1 and Y2 respectively independently represent hydrogen, electron-withdrawing groups or electron-donating groups; at least one of X1 and X2 represents a substituent represented by formula II (shown in the description); M represents -S-, -P-, -SO-, -SO2-, -S(=S)-, -S(=S)(=S)-, -PO-, -PO2-, -P(=S)-, -P(=S)(=S)- and -C(=O)-; N1, N2, N3 and N4 respectively independently represent carbon atoms or nitrogen atoms; and n represents an integer of 0-4. The spirobifluorene compound disclosed by the invention has an A-D-A chemical structure, and a spatial dihedral angle close to 90 degrees is formed between an electron-donating D unit and an electron-withdrawing A unit, so that HOMO-LUMO track separation of a fluorescent material is beneficially thermally activated and delayed, so as to obtain ideal deltaEST.

Fluorinated 9,9′-spirobifluorene derivatives as host materials for highly efficient blue organic light-emitting devices

A series of new fluorinated 9,9′-spirobifluorene derivatives (SFs) have been designed and synthesized for organic light-emitting devices (OLEDs). The spatial structure of 2,2′,7,7′-tetrakis(2,4-bifluorophenyl) spiro-9,9′-bifluorene was determined by X-ray diffraction analysis. With the different substitution patterns of electron-withdrawing groups, such as F and CF3, the photophysical properties, energy levels and thermal stabilities of these SFs can be tuned, which is supported by density functional studies of their geometries and electronic structures. A non-doped deep blue OLED using 2,2′,7,7′-tetrakis(3-fluorophenyl)spiro-9,9′- bifluorene (Spiro-(3)-F) as the emitter shows excellent Commission Internationale de l'Eclairage (CIE) coordinates of (0.169, 0.122) with emission peaking at ca. 408 nm. Furthermore, these SFs serve as an excellent host material for the 4,4′-bis(9-ethyl-3-carbazovinylene)-1,1′- biphenyl dopant to form high-performance OLEDs with low turn-on voltages and high efficiencies, especially for Spiro-(3)-F as the fluorescent host with pure blue CIE coordinates of (0.149, 0.187), a low turn-on voltage of 3.4 V, high luminance of over 10 000 cd m-2, a high current efficiency of 6.66 cd A-1, and a high external quantum efficiency of 4.92%. The high efficiency is attributed to the high carrier mobility together with the low injection barriers for both the electron and the hole in the Spiro-(3)-F-based device.