67665-47-8

Basic information

• Product Name: 2,2'-DIBROMO-9,9'-SPIROBIFLUORENE
• Synonyms: DibroMo-9,9'-spirobi[9H;9,9'-Spirobi[9H-fluorene],2,2'-dibroMo-;2,2'-DIBROMO-9,9'-SPIROBIFLUORENE;2,2'-Dibromo-9,9'-spirobi[9H-fluorene]
• CAS NO: 67665-47-8
• Molecular Formula: C₂₅H₁₄Br₂
• Molecular Weight: 474.18666
• EINECS: 1312995-182-4
• Product Categories: Fluorene Derivatives
• Mol File: 67665-47-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 240°C(lit.)
• Boiling Point: 557.4 °C at 760 mmHg
• Flash Point: 335.1 °C
• Appearance: /
• Density: 1.74
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,2'-DIBROMO-9,9'-SPIROBIFLUORENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-DIBROMO-9,9'-SPIROBIFLUORENE(67665-47-8)
• EPA Substance Registry System: 2,2'-DIBROMO-9,9'-SPIROBIFLUORENE(67665-47-8)

Safety Data

• Hazardous Substances Data: 67665-47-8(Hazardous Substances Data)

Usage

Chemical Properties

off-white powder

Upstream product

• 159-66-0 9,9'-spirobifluorene 
• 67665-45-6 2,2′-diamino-9,9′-spirobifluorene 
• 864957-74-4 bis(4'-bromobiphenyl-2-yl)methanone 
• 864957-73-3 bis(4'-trimethylsilanylbiphenyl-2-yl)methanone 
• 486-25-9 9-fluorenone 
• 2052-07-5 2-Bromobiphenyl 
• 67665-44-5 9-((1,1'-biphenyl)-2-yl)-9H-fluoren-9-ol 
• 98-80-6 phenylboronic acid 
• 583-53-9 2,3-dibromobenzene 
• 86-73-7 9H-fluorene 
• 17865-11-1 (4-(trimethylsilyl)phenyl)boronic acid 
• 106-37-6 1.4-dibromobenzene 
• 180577-88-2 4'-trimethylsilylbiphenyl-2-carboxylic acid methyl ester 

Downstream Products

• 445498-72-6 2,2'-bis(4-hexyl-2-thienyl)-9,9'-spirobifluorene 
• 445498-74-8 C₆₅H₇₂S₄ 
• 790674-48-5 (rac)-2,2'-diiodo-9,9'-spirobifluorene 
• 445498-73-7 2,2'-bis(5-bromo-4-hexyl-2-thienyl)-9,9'-spirobifluorene 
• 445498-75-9 C₆₅H₇₀Br₂S₄ 
• 67665-48-9 2,2'-dicyano-9,9'-spirobifluorene 
• 73100-47-7 2,2'-dimethyl-9,9'-spirobifluorene 

Relevant articles and documents

Synthesis and characterization of spiro-linked poly(terfluorene): A blue-emitting polymer with controlled conjugated length

The synthesis and characterization of a fluorene-spirobifluorene alternating copolymer, P(OF-SBF), are described. In the case of the spiro-segment, the two fluorene rings are orthogonally arranged and connected through a tetrahedral bonding carbon atom (t

Electron Transfer around a Molecular Corner

The distance dependence of electron transfer (ET) is commonly investigated in linear rigid rod-like compounds, but studies of molecular wires with integrated corners imposing 90° angles are very rare. By using spirobifluorene as a key bridging element and by substituting it at different positions, two isomeric series of donor-bridge-acceptor compounds with either nearly linear or angled geometries were obtained. Photoinduced ET in both series is dominated by rapid through-bond hole hopping across oligofluorene bridges over distances of up to 70 ?. Despite considerable conformational flexibility, direct through-space and through-solvent ET is negligible even in the angled series. The independence of the ET rate constant on the total number of fluorene units in the angled series is attributed to a rate-limiting tunneling step through the spirobifluorene corner. This finding is relevant for multidimensional ET systems and grids in which individual molecular wires are interlinked at 90° angles.

Improved synthesis of 2,2′-Dibromo-9,9′-spirobifluorene and its 2,2′-bisdonor-7,7′-bisacceptor-substituted fluorescent derivatives

(Chemical Equation Presented) Pure 2,2′-Dibromo-9,9′- spirobifluorene was synthesized by a method that did not involve troublesome dibromination of 9,9′-spirobifluorene or Sandmeyer reaction of 2,2′-diamino-9,9′-spirobifluorene. A series of donor-acceptor orthogonally substituted 9,9′-spirobifluorene was subsequently prepared showing rich variation of fluorescence in solution and in solid state.

Head-to-tail regioregular oligothiophene-functionalized 9,9′-spirobifluorene derivatives. 1. Synthesis

Two series of novel fully conjugated oligomers, oligothiophene-functionalized 9,9′-spirobifluorene derivatives, have been developed in this contribution. First, four 9,9′-spirobifluorene bromide derivatives (compounds 1a-d) are prepared through various synthetic routes. Oligothiophene derivatives with or without substituents are synthesized through the Grignard and Suzuki coupling reactions. The Negishi coupling reactions between oligothienylzinc chloride and various 9,9′spirobifluorene bromides with Pd(PPh3)4 as catalyst successfully produce the desired compounds, unsubstituted oligothiophene-functionalized 9,9′-spirobifluorene derivatives, compounds 2 to 4ad. Since the Negishi coupling reactions afford regioregularly head-to-tail (H-T) oligo(4-nhexylthiophene)-functionalized 9,9′-spirobifluorene derivatives in poor yields, the Suzuki coupling reactions between sodium 4-n-hexylthienyl-2-boronate 8, and various 9,9′-spirobifluorene-based bromides 1a-d and 9-16 are employed to produce highly regioregular head-to-tail oligothiophenefunctionalized 9,9′-spirobifluorene derivatives (compounds 5 to 7a-d) in very high yields. We also investigate the effect of solvents on the Suzuki coupling reactions. The structure and purity of all compounds are verified by FT-IR, 1H and 13C NMR, MS, and elemental analysis.