171408-76-7

Basic information

• Product Name: 2-Bromo-9,9'-spirobi[9H-fluorene]
• Synonyms: 9,9′-Spirobi[9H-fluorene],2′-bromo;2-BROMO-9,9''-SPIROBIFLUOROENE;2-Bromo-9,9'-spirobi[9H-fluorene];2-Bromo-9,9'-spirobi;2-BroMo-9,9'-spirobiflu;2-BroMo-9,9'-spirobifluoren;2-broMo-9,9'-Spirobi[9H]-fluorene (BSBF);2- broMospirofluorene
• CAS NO: 171408-76-7
• Molecular Formula: C₂₅H₁₅Br
• Molecular Weight: 395.29
• EINECS: 1312995-182-4
• Product Categories: Fluorene Derivatives;Fluorene Series;OLED materials,pharm chemical,electronic;Pyridines
• Mol File: 171408-76-7.mol
• Article Data: 30

Chemical Properties

• Melting Point: 182.0 to 186.0 °C
• Boiling Point: 517.213 °C at 760 mmHg
• Flash Point: 259.774 °C
• Appearance: off-white crystal
• Density: 1.522 g/cm³
• Vapor Pressure: 0-0.001Pa at 20-50℃
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-Bromo-9,9'-spirobi[9H-fluorene](CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-9,9'-spirobi[9H-fluorene](171408-76-7)
• EPA Substance Registry System: 2-Bromo-9,9'-spirobi[9H-fluorene](171408-76-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 171408-76-7(Hazardous Substances Data)

Usage

Description

2-Bromo-9, 9’-spirobifluorene is a derivative of 9,9'-spirobifluorene. It is a quite useful blue light emitting material used in the organic light emitting diodes (OLEDs). It possesses high photoluminescence efficiency and good chemical stability. Moreover, It has high glass-transition temperature, excellent thermal stability and easy color tenability through introducing low band gap co-monomers.

Chemical Properties

Off-white to light yellow crystal or powder

Synthesis

Synthesis of 2-bromo-spirofluorene2-bromo-9-hydroxy-9-(2-biphenyl)fluorene (2g) dissolved in 25 mL acetic acid (15 mol/L) containing hydrochloric acid (12 mol/L) was refluxed for about 2 h to separate out a white solid, which was recrystallized with ethanol to produce white crystals of 2-bromo-spirofluorene (1.2 g, yield 63%). GC-MS (m/z +): 394. 1HNMR (400 MHz, CDCl3, ppm):δ7.80～7.86 (m, 3H), δ7. 70 (d, 1H),δ7.48 (m, 1H), δ7.36 ～ 7.40 (m, 3H), δ7.13 (m, 3H), δ6.84 (d, 1H), δ6.72 (m, 3H)

References

http://www.sigmaaldrich.com/catalog/product/aldrich/767735?lang=en®ion=USTang, S., et al. "A Molecular Glass for Deep-Blue Organic Light-Emitting Diodes Comprising a 9,9′-Spirobifluorene Core and Peripheral Carbazole Groups." Advanced Functional Materials 17.15(2010):2869-2877.Nakanotani, H., et al. "Extremely Low-Threshold Amplified Spontaneous Emission of 9,9′-Spirobifluorene Derivatives and Electroluminescence from Field-Effect Transistor Structure." Advanced Functional Materials17.14(2010):2328-2335.

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Downstream Products

• 236389-21-2 9,9'-spirobi[9H-fluoren]-2'-yl-boronic acid 
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Relevant articles and documents

Side chain modification on PDI-spirobifluorene-based molecular acceptors and its impact on organic solar cell performances

N-Substitution in perylene diimide (PDI) n-type semiconductors is critical for their performance in organic bulk heterojunction solar cells. In this work we synthesized and compared three perylene diimide-spirobifluorene derivatives, N-substituted with different alkyl side groups. These molecular systems were obtained by cost-effective methods, using straightforward synthetic procedures and easy purification. These PDI derivatives were used as electron acceptor materials, blended with a benchmark quinoxaline-benzodithiophene based donor polymer, in bulk heterojunction solar cells. All devices were processed by blade coating in air, and also using non-chlorinated solvents. The three molecules presented identical HOMO/LUMO energy levels and very similar optical properties but different photovoltaic responses. These different performances were discussed through optical, electrical and morphological characterizations. The highest power conversion efficiency was achieved for the active layer based on the derivative with branched and longer alkyl groups in N-positions, which favored a morphology with reduced donor:acceptor phase segregation.

Poly(vinylspirobifluorene): Synthesis and properties of a novel styrenic polymer

Synthesis and properties of a new class of styrenic polymer are reported. The radical polymerization of 2-vinyl-9,9′-spirobifluorene yielded high molecular weight poly(vinylspirobifluorene) with high thermal stability and high solubility, which gave a self-standing transparent film with high refractive index. Copyright

Organic electroluminescent compound and organic electroluminescent device containing same

The invention discloses an organic electroluminescent compound, which is formed by connecting a structural formula (1) and a structural formula (2), wherein * is a connecting site, the structural formula (1) and the structural formula (2) are defined in the specification, Y is O or S, X1-X8 are independently C-R5 or N, Z1-Z4 are independently C-R6 or N, the structural formula (1) can be connected with any non-N connecting site in Z1-Z4 on the A ring of the structural formula (2), and Ar is a substituted or unsubstituted C6-C60 aromatic hydrocarbon group or a substituted or unsubstituted C5-C60 heteroaromatic hydrocarbon group. When the organic electroluminescent compound is applied to the organic electroluminescent device, under the same current density, the luminous efficiency is greatly improved, the color purity is high, the starting voltage of the device is reduced, the power consumption of the device is relatively reduced, and the service life of the device is correspondingly prolonged.

Method for synthesizing 9,9'-spirobifluorene derivative

The invention relates to a method for synthesizing a 9,9'-spirobifluorene derivative, and belongs to the field of organic chemical synthesis. The method comprises the following steps: activating a C-Fbond in tetrahydrofuran under inert gas protection through reduction and lithiation reaction of raw materials of 2-fluorobiphenyl and a metal lithium sheet, thus establishing 2-biphenyl lithium; thenenabling the 2-biphenyl lithium to react with a fluorenone derivative, hydrolyzing, drying a solvent by distillation, and carrying out ring closing on solid in acetic acid, thus synthesizing the 9,9'-spirobifluorene derivative. According to the method disclosed by the invention, the 2-fluorobiphenyl in low cost is adopted as a raw material to replace 2-bromobiphenyl commonly adopted by a traditional method, the production cost is low, and reaction conditions are gentle; an applicable substrate range of the method is wide, and a new thought is provided for synthesis of the 9,9'-spirobifluorenederivative.